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Original: publisher page

Siddhi S. Hate, Susan M. Reutzel-Edens, Lynne S. Taylor* · Molecular Pharmaceutics (Just Accepted Manuscript, published on the web 06 Dec 2018) (2018)

Insight into Amorphous Solid Dispersion Performance by Coupled Dissolution and Membrane Mass Transfer Measurements

In a high-surface-area hollow-fiber apparatus that measures dissolution and membrane transport together, atazanavir solutions and ASDs that exceed the amorphous solubility and form drug-rich nanodroplets transferred more drug across the membrane, and the absorptive sink sped up release from slow-dissolving ASDs.

Abbreviations

ATZ atazanavir; ASD amorphous solid dispersion; DL drug loading (wt% drug in the ASD; 90:10, 70:30, 50:50 = polymer:ATZ, i.e. 10, 30, 50% DL); AS amorphous solubility; LLPS liquid-liquid phase separation; HPMC hydroxypropyl methylcellulose; HPMCAS hydroxypropyl methylcellulose acetate succinate; PVPVA polyvinylpyrrolidone/vinyl acetate (Kollidon VA 64); Cmax maximum receiver concentration; AUC area under the receiver concentration-time curve; DLS dynamic light scattering; NTA nanoparticle tracking analysis; PDI polydispersity index; I(369)/I(329) ratio of ATZ fluorescence emission intensities at 369 and 329 nm; Diss closed-compartment (non-sink) dissolution; Diss-Abs simultaneous dissolution-absorption; PLM polarized light microscopy; SI p. = page of the supporting information (PDF index).

Graphical abstract: An ASD with or without LLPS feeding the hollow fiber module
Graphical abstract · p.33 · An ASD with or without LLPS feeding the hollow fiber moduleShows. the LLPS case gives the higher receiver curve.

Story. Why they did it → how → what they found → how it fits together → what is left. Each part opens with the short version; "More detail" under it gives the full account. Grey ids open the evidence behind a sentence.

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Question

How do liquid-liquid phase separation and drug-rich nanodroplets, made by solvent shift or by dissolving ASDs of different drug loading and polymer, change drug transfer across a membrane when dissolution and absorption run together?

Short answer

Above the amorphous solubility (78 µg/mL), receiver Cmax kept rising with donor concentration (≈8.5 → ≈13.8 µg/mL from 100 to 500 µg/mL), at a lower slope, while droplet number rose. ·· The 10% loading HPMCAS and HPMC ASDs, the ones that formed nanodroplets, transferred the most drug (AUC ≈1220 and ≈1170 µg·min/mL). · The absorptive sink increased release from all 50% loading ASDs.

Conclusion

For atazanavir in pH 6.8 buffer at 37 °C with a 15 nm cellulosic hollow-fiber membrane, the authors conclude that drug-rich nanodroplets, whether made by solvent shift or by ASD dissolution, increase the amount of drug transferred, and that transfer keeps increasing with concentration above the amorphous solubility, in correlation with droplet number. ·· They read the slope change as a change in the mass transfer coefficient ("This shows"; "logically" from the rising droplet number), but neither free drug nor the coefficient was measured, and the mechanism is left open between Brownian-motion convection in the boundary layer ("Possibly"), dissolution-rate-limited absorption ("Alternatively") and higher solubility of shrinking droplets ("it is plausible"). ···· Among nine ASDs of HPMCAS, HPMC and PVPVA, only the 10% drug loading ones dissolved above the amorphous solubility; the HPMCAS and HPMC ones formed nanodroplets and transferred the most drug, the PVPVA one formed agglomerates that sustained transfer over 2 h but less well over 4 h, and the crystallizing 50:50 PVPVA ASD transferred the least. ···· The absorptive compartment increased release from all 50% drug loading ASDs and changed their ranking by polymer, so the authors recommend absorptive dissolution testing for "a more meaningful comparison" of formulations; the in vivo relevance "needs further investigation". ···

01Why this study

Known 1Supersaturation raises flux; solubilizers do not

Flux follows the chemical potential difference across the membrane, so supersaturated solutions raise it, while solubilizing additives lower drug activity.

Cussler 2009, ref 10; Raina 2015, ref 4 ·

Known 2Above the amorphous solubility, the solution splits

Drug-rich nanodroplets coexist with a water-rich phase held at the amorphous solubility, which caps free drug.

Ilevbare 2013, ref 23; Taylor 2016, ref 11

Known 3Nanodroplets act as a reservoir

In side-by-side cells they kept flux at its maximum until they were used up.

Indulkar 2016, ref 12; Raina 2014, ref 13 ·

Known 4Standard tests miss absorption

Closed dissolution tests have no sink, and two-compartment cells have small membranes and need many hours.

McAllister 2010, ref 28; Hate 2017, ref 31 ··

Gap → this paperHow do nanodroplets and ASD formulation variables affect membrane transport when dissolution and absorption are coupled at a biorelevant rate?
More detail

What was already known. The introduction builds on these points (numbered reference list):

  • Two formulation routes, two effects on transport. Solubilizing additives raise the equilibrium concentration but have been reported to leave membrane transport unchanged or to lower it, because they lower drug thermodynamic activity (Raina 2015, ref 4; Miller 2011, ref 5). Supersaturating formulations give intraluminal concentrations above equilibrium solubility and can enhance absorption (refs 6-9).
  • Flux follows chemical potential. The driving force for membrane transport is the chemical potential difference across the membrane (Cussler 2009, ref 10), so supersaturated solutions give higher flux, as long as the drug does not crystallize over biorelevant times (refs 11-13). Supersaturation can arise from amorphous solids, ASDs, salts, pH shifts, cocrystals and lipid formulations (Almeida e Sousa 2016, ref 14); ASDs generate and maintain it, with the polymer lowering the risk of crystallization (refs 15-19). ··
  • LLPS and the amorphous solubility. Highly supersaturated solutions of hydrophobic drugs may undergo LLPS into disordered colloidal aggregates, a precursor to crystallization (refs 20-22). Above the amorphous solubility the solution splits into a drug-rich phase, typically nanodroplets of water-saturated amorphous drug, and a water-rich phase at the amorphous solubility; activity is equal in both, the two are in metastable equilibrium until crystals nucleate, and the amorphous solubility is the highest free drug concentration possible (Ilevbare 2013, ref 23; Taylor 2016, ref 11; Indulkar 2016, ref 12; Raina 2014, ref 13; refs 24-26). ·
  • Nanodroplets as a reservoir. In vitro, without crystallization, nanodroplets replenished the aqueous phase from which drug crossed the membrane until the drug-rich phase was depleted; flux stayed high while supersaturation was constant, for a time set by the amount of drug in the drug-rich phase and how fast it dissolves. Nanodroplets "may potentially" enhance bioavailability (Indulkar 2016, ref 12). Drug-rich colloids have also been suggested to thin the unstirred water layer and raise effective permeability in vivo (Stewart 2017, ref 27). ·
  • Closed dissolution tests lack a sink. USP dissolution testing is a closed, one-compartment setup that "often fails" to predict supersaturating formulations, and modified apparatuses still lack an absorptive sink (McAllister 2010, ref 28; Kostewicz 2014, ref 29). Removing drug by absorption can change both dissolution and crystallization; crystallization was less extensive with an absorptive membrane (Bevernage 2012, ref 30; Hate 2017, ref 31). ·
  • Two-compartment cells are slow. Their membranes are small, and since mass transfer rate is proportional to membrane area, experiments are long, receiver concentrations low and an unstirred water layer slows transfer further (Indulkar 2016, ref 12; Sironi 2017, ref 35). The flow-through side-by-side study of refs 12-13 needed 16 h to follow depletion of the drug-rich phase, against a biorelevant intestinal absorption time of 3-4 h. ··
  • The new apparatus. The group's hollow-fiber module gives a large membrane area per volume, continuous flow on both sides that reduces the unstirred water layer, controlled hydrodynamics "potentially more similar" to in vivo, sink conditions through fresh receiver fluid and in-line receiver measurement; its robustness and sensitivity were described earlier (Hate 2017, ref 31; refs 36-38).
  • Why atazanavir, and what varies in ASDs. ATZ crystallizes relatively slowly, and enough of certain polymers inhibits its crystallization for more than 4 h (Indulkar 2018, ref 39). Drug loading and polymer type can change release rate, solution concentration and phase behaviour (Simonelli 1969, ref 40; Simonelli 1976, ref 41), and nanodroplets with higher diffusive flux have formed during dissolution of some ASDs (Jackson 2015, ref 15; Alonzo 2011, ref 42). ·

What the paper set out to do. Use the absorptive dissolution apparatus to understand dissolution and absorption of supersaturating systems that undergo LLPS: test solutions below and above the amorphous solubility, characterize the nanodroplets by number and size, measure simultaneous dissolution and absorption of ASDs of different drug loading and polymer, and compare with closed-compartment dissolution to see how the absorptive compartment changes the dissolution rate. ··

02How they approached it

One weakly basic, slow-crystallizing drug, unionized at pH 6.8, tested first as solutions of set supersaturation and then as nine ASDs; each ASD was dissolved both in a closed vessel and with the absorptive sink, and nanodroplets were tracked by fluorescence, DLS and NTA. ·····

ATZ solutionssolvent shift, 1 mg/mL HPMCAS30-500 µg/mL, from below to above the amorphous solubility; measured. ·
Solvent-shift solutions with HPMC or PVPVA1 mg/mL polymerCompared for nanodroplet size and fluorescence; the PVPVA droplets agglomerate; measured. ··
HPMCAS ASDscellulose ester, MF grade10, 30 and 50% drug loading; only 10% forms nanodroplets; measured. ·
HPMC ASDscellulose ether10, 30 and 50% drug loading; behave like the HPMCAS ASDs; measured. ··
PVPVA ASDsKollidon VA 6410, 30 and 50% drug loading; PVPVA raises the amorphous solubility to 94 µg/mL; the 10% ASD gives agglomerates and the 50% ASD crystallizes with absorption; measured. ···

What was done

Experiment

Solvent-shift solutions 30-500 µg/mL→fluorescence ratio, DLS, NTA→onset, size and number of nanodroplets.·······

↓
Experiment

Same solutions through the hollow-fiber module at 4 mL/min for 100 min→receiver profiles→Cmax and AUC vs donor concentration.··

↓
Experiment

Nine ASDs in closed-compartment dissolution, 200 µg/mL dose→apparent concentration and nanodroplet checks.···

Experiment

Same nine ASDs with simultaneous dissolution-absorption→donor and receiver profiles→AUC over 120 min.··

↓
Comparison

Solvent shift vs 90:10 HPMCAS ASD over 240 min→receiver profiles and droplet depletion.

Experiment

90:10 HPMCAS at 100, 200 and 500 µg/mL dose→receiver profiles.

Comparison

50% loading ASDs closed vs with absorption→total drug released.·

Experiment

10% loading ASDs over 4 h→how long the reservoir lasts.

More detail

What was done

  1. Solubility. Crystalline solubility was measured after 48 h with excess solid in pH 6.8, 50 mM phosphate buffer at 37 °C, by UV at 278 nm after centrifugation. The amorphous solubility (LLPS onset) was found by adding a 30 mg/mL methanolic ATZ stock at 40 µL/min to 50 mL buffer with 1 mg/mL HPMCAS at 37 °C and noting where scattering at 400 nm appeared; the same was done with 1.8 mg/mL PVPVA. ··
  2. Detecting nanodroplets. ATZ is autofluorescent: excited at 250 nm it emits at 329 nm, and a second band at 369 nm appears in a drug-rich environment, so I(369)/I(329) marks droplet formation and later their depletion. DLS (173°, 37 °C, filtered through 1 or 0.45 µm glass fiber filters) gave size and PDI; NTA in fluorescence mode with 1 µg/mL Nile red counted droplets, since HPMCAS solutions alone gave a high background. ····
  3. Solution mass transport. The donor (50 mL buffer with 1 mg/mL HPMCAS, ATZ added from a 25 mg/mL methanolic stock to 30-500 µg/mL) and fresh receiver buffer were pumped co-currently at 4 mL/min each through a cellulosic hollow fiber membrane (100 cm², 15 nm pores) at 37 °C for 100 min; the receiver was read by an in-line UV probe. Each run was followed by a 30 min 50% methanol wash, which recovered about 5-10% of the drug. ·
  4. ASDs. ASDs of 10, 30 and 50 wt% ATZ in HPMCAS, HPMC or PVPVA were made by rotary evaporation from methanol (HPMC: 1:1 dichloromethane:methanol) at 45 °C, vacuum-dried, cryo-milled and stored at 0% RH; all were X-ray amorphous. ··
  5. Closed vs absorptive dissolution. ASD powder equal to 200 µg/mL ATZ was suspended in 50 mL buffer at 37 °C, either stirred at 300 rpm in a closed vessel for 120 min or as the donor of the absorptive apparatus for 2 h (a 10 or 70 µm cannula filter kept particles out of the fibers). Donor concentration came from a UV dip probe, receiver from a flow-through UV cell; nanodroplets were checked by fluorescence, DLS and NTA, and crystals by polarized light microscopy. ··
  6. Further runs. 90:10 HPMCAS at 100, 200 and 500 µg/mL dose; the 10% loading ASDs for 4 h; solvent shift vs ASD over 240 min. ··

Key equations

Cmax fits (Fig. 4)
Cmax=0.07Cd+1.56(Cd<Cam)Cmax=0.01Cd+6.81(Cd>Cam)

Receiver Cmax rises with initial donor concentration C_d several times more steeply below the amorphous solubility C_am than above it, but it keeps rising; the paper prints the intercept as "1,56", and the above-AS line does not reproduce its own points, which rise about 0.013 µg/mL per µg/mL.·

AUC fits (Fig. 4)
AUC=5.51Cd+206.49AUC=1.29Cd+693.88

The same break for the area under the receiver curve (µg·min/mL): the slope falls about four-fold above the amorphous solubility but stays positive.·

Amount transferred (p.18)
mtransferred=Q×AUC

With the receiver flow Q = 4 mL/min, the area under the receiver curve gives the mass of drug carried across; Fig. 6G plots the AUC itself.

Total released with absorption (Fig. 9)
mreleased(t)=mdonor(t)+mtransferred(t)

In the absorptive runs the dissolved drug is counted in both compartments.

Terms used on this page
  • Amorphous solubility: the highest free drug concentration before the solution splits into a drug-rich and a water-rich phase (liquid-liquid phase separation, LLPS). The drug-rich phase appears as nanodroplets (colloidal drug-rich species).
  • Donor and receiver: the two streams on either side of the membrane; the receiver is fresh buffer pumped once through (sink). Non-cumulative receiver concentration = drug crossing in one pass.
  • Cmax: the highest receiver concentration; AUC: area under the receiver concentration-time curve.
  • Solvent shift: making a supersaturated solution by adding a concentrated drug solution in organic solvent to buffer.
  • I(369)/I(329): ratio of ATZ fluorescence at 369 and 329 nm; about 0.6 at the amorphous solubility, higher when droplets are present.
  • PDI: polydispersity index of DLS; low values mean a narrow size distribution.
  • Diss and Diss-Abs: closed-compartment dissolution and simultaneous dissolution-absorption.
  • 90:10, 70:30, 50:50: polymer:drug weight ratio, i.e. 10, 30 and 50% drug loading.

03Main findings

1

Above 78 µg/mL atazanavir forms droplets of about 200 nm, more of them at higher concentration

Crystalline solubility was 5 µg/mL and amorphous solubility 78 µg/mL. · Above it, the fluorescence ratio rose from ≈0.58 at 75 to ≈2.14 at 500 µg/mL, droplets stayed at 204-226 nm, and the NTA count roughly doubled from 75 to 100 and again to 150 µg/mL. ··

Fig. 2: Droplet number by NTAFig. 2: Droplet number by NTA
Fig. 2 · p.11-12 · Droplet number by NTAShows. (A) particle concentration roughly doubles from 75 to 100 and from 100 to 150 µg/mL; (B-D) denser fields of fluorescent droplets.Also supports K2
More detail

At pH 6.8 and 37 °C, crystalline ATZ dissolved to 5 (± 0.5) µg/mL, and LLPS began at 78 (± 5) µg/mL in buffer with 1 mg/mL HPMCAS; both values refer to the unionized drug (pKa printed as 4.52 and as 4.42). ··· Solutions below the amorphous solubility were clear and single-phase, those above it turbid. The fluorescence ratio stayed at ≈0.30-0.36 from 30 to 60 µg/mL, reached ≈0.58 at 75 µg/mL (0.58 is also the stated value at the amorphous solubility) and rose to ≈0.78, ≈1.09, ≈1.21, ≈1.42 and ≈2.14 at 100, 150, 200, 300 and 500 µg/mL. Above the amorphous solubility the spectrum shows a second band at 369 nm beside the 329 nm band. ·· DLS gave 204-226 nm droplets with PDI 0.08-0.15 from 100 to 500 µg/mL, while the derived count rate rose from 28633 to 342132 kcps. NTA counted ≈2.3 × 10⁹, ≈5.4 × 10⁹ and ≈1.06 × 10¹⁰ particles per mL at 75, 100 and 150 µg/mL; higher concentrations held too many particles to track. The authors read constant size with stronger fluorescence as more droplets ("it was intuitive") and say NTA "confirmed" it. ·

Fig. 1: Fluorescence ratio vs atazanavir concentration
Fig. 1 · p.10 · Fluorescence ratio vs atazanavir concentrationShows. I(369)/I(329) passes the dashed amorphous-solubility level at 75-100 µg/mL and keeps rising to ≈2.1 at 500 µg/mL.
2

Transfer keeps rising above the amorphous solubility, at a lower slope

Receiver Cmax rose from ≈3.6 to ≈6.8 µg/mL between 30 and 75 µg/mL and from ≈8.5 to ≈13.8 µg/mL between 100 and 500 µg/mL; the fitted AUC slope fell from 5.51 to 1.29 above the amorphous solubility, with no plateau. ·· The authors read this as a change in the mass transfer coefficient tied to droplet number. ·

Fig. 4: Cmax and AUC vs donor concentration
Fig. 4 · p.14 · Cmax and AUC vs donor concentrationShows. red Cmax (left axis) and black AUC (right axis) rise steeply up to the amorphous solubility (dashed) and less steeply, but without a plateau, above it.Read it as. the printed above-AS Cmax equation does not match its points; trust the points.Also supports K1
More detail

Receiver profiles reached steady state within 10 min, peaked and then declined over 100 min; the authors attribute the decline to the falling donor concentration. · Peaks were ≈3.9, ≈5.6, ≈6.6 and ≈7.0 µg/mL for 30-75 µg/mL and ≈8.7, ≈10.1, ≈10.8, ≈12.5 and ≈13.8 µg/mL for 100-500 µg/mL; at 100 µg/mL the profile fell below the Cmax of a solution at the amorphous solubility after ≈60 min, while the higher concentrations stayed above it. In Fig. 4, Cmax and AUC rise steeply up to the amorphous solubility (Cmax fit slope 0.07, AUC 5.51) and less steeply above it (0.01 and 1.29); AUC went from ≈350 to ≈580 µg·min/mL below and from ≈710 to ≈1270 above. ···· Below the amorphous solubility this is the expected effect of a higher driving force ("as expected"). Above it, activity and free drug are taken to be constant, and in a side-by-side cell the authors expect a single maximum; the continued rise here "shows" a different mass transfer coefficient with nanodroplets. · Since the ≈200 nm droplets cannot pass the 15 nm pores and their contribution to diffusivity should be negligible, they conclude that "logically" the rise comes from the growing number of droplets. ·· The above-AS Cmax fit as printed does not reproduce its points, but the slope break holds.

Fig. 3: Receiver profiles for 30-500 µg/mL solutions
Fig. 3 · p.13 · Receiver profiles for 30-500 µg/mL solutionsShows. profiles stack upward with concentration, also above the dashed line (Cmax at the amorphous solubility).
3

Only the 10% loading ASDs exceed the amorphous solubility, and only the cellulose ones give detectable nanodroplets

In closed dissolution the 90:10 HPMCAS and HPMC ASDs reached apparent ≈240-250 µg/mL with ≈300 nm droplets, while 30 and 50% loadings dissolved more slowly and formed no nanodroplets. · PVPVA raised the amorphous solubility to 94 µg/mL; its 10% ASD gave no droplets in filtered samples (ratio 0.26) but 0.89 unfiltered. ·

Fig. 5: Closed-compartment dissolution of the nine ASDs
Fig. 5 · p.16 · Closed-compartment dissolution of the nine ASDsShows. (A) HPMCAS, (B) HPMC, (C) PVPVA; only the 90:10 ASDs rise well above the dashed amorphous-solubility line.
More detail

The apparent UV concentration is not quantitative above the amorphous solubility, since droplets absorb and scatter light; the 90:10 HPMCAS ASD reached ≈240 µg/mL (≈248 at 120 min) and the 90:10 HPMC ASD ≈253 µg/mL, above the 200 µg/mL dose. ·· For these two, fluorescence ratios of 1.17-1.30 and DLS sizes of 294-326 nm confirmed nanodroplets, slightly larger than solvent-shift droplets made with 1 mg/mL of the same polymer (221 and 311 nm). · The 30 and 50% ASDs of HPMCAS and HPMC rose slowly to ≈84-99 µg/mL by 120 min, with no nanodroplets observed; the authors call the maximum "consistent with" not exceeding the amorphous solubility, although some curves end slightly above the drawn line. ·· Slower dissolution at higher loading has been seen before and "is thought to" stem, in some cases, from a drug-rich surface layer on the ASD. PVPVA ASDs at 30 and 50% dissolved at a moderate and slow rate without LLPS (≈91 and ≈73 µg/mL at 120 min). · The 90:10 PVPVA ASD plateaued at ≈110-130 µg/mL; pre-dissolved PVPVA at 1.8 mg/mL raised the amorphous solubility to 94 µg/mL, which the authors use to explain concentrations above 78 µg/mL. ·· Its filtered samples showed no 369 nm band and no DLS scatterers, but the unfiltered ratio of 0.89 points to a drug-rich phase; "Most likely" droplets formed in the boundary layer agglomerated quickly. · In a 200 µg/mL solvent-shift solution with 1 mg/mL PVPVA, droplets grew from ≈245 nm to ≈700 nm at 75 min and ≈10 µm at 105 min. ·

4

Nanodroplet-forming ASDs transfer the most drug; the crystallizing ASD the least

Over 120 min of dissolution-absorption, AUC was ≈1220 and ≈1170 µg·min/mL for 90:10 HPMCAS and HPMC, ≈985 for 90:10 PVPVA and ≈555-760 for the 50:50 ASDs. The 50:50 PVPVA ASD crystallized from ≈80 min and transferred the least. ·

Fig. 6: Dissolution-absorption of the nine ASDs, and AUC
Fig. 6 · p.19 · Dissolution-absorption of the nine ASDs, and AUCShows. donor (left) and receiver (right) for HPMCAS, HPMC and PVPVA; arrows mark crystallization of 50:50 PVPVA; (G) AUC over 120 min is highest for the 90:10 cellulose ASDs.Also supports K4
More detail

With absorption, the 90:10 HPMCAS and HPMC donors peaked at ≈195-200 µg/mL and declined to ≈127 µg/mL by 120 min instead of plateauing; the authors attribute the decline to absorption removing nanodroplets. · Their receivers peaked at ≈10.0 and ≈9.4 µg/mL, in line with solvent-shift solutions of similar concentration, and stayed above the level of a solution at the amorphous solubility (≈7.6 µg/mL) for 120 min, "in part" because droplets replenished absorbed drug. ·· The 70:30 HPMCAS ASD stayed slightly below the amorphous solubility, with a receiver plateau of ≈6.0 µg/mL from about 20-30 min, and the 50:50 HPMCAS donor approached the amorphous solubility only after about 100 min; HPMC behaved similarly. ·· The 90:10 PVPVA donor plateaued slightly above the amorphous solubility with no discernable nanospecies ("potentially" agglomerates plus polymer solubilization); its receiver (≈8.8 µg/mL) stayed constant, which the authors read as a reservoir of micron-sized agglomerates ("Most likely"). ·· The 70:30 PVPVA ASD peaked within 20 min near the amorphous solubility. · The 50:50 PVPVA ASD released slowly and, from ≈80 min, donor and receiver concentrations fell as the donor crystallized; polarized light microscopy showed birefringent crystals at 100 min. · Fig. 6G ranks the AUC: 90:10 HPMCAS ≈1220, 90:10 HPMC ≈1170, 90:10 PVPVA ≈985, 50:50 HPMC ≈760, 50:50 HPMCAS ≈660, 50:50 PVPVA ≈555 µg·min/mL. The authors say the cellulose 10% ASDs "clearly showed higher amounts", and that integrating the receiver curve reveals effects of dissolution rate, nanodroplets and crystallization that dissolution profiles hide. · The plotted quantity is AUC; the mass is AUC × 4 mL/min. ·

5

ASD and solvent-shift nanodroplets behave alike, and more droplets sustain transfer longer

Receiver profiles from a 90:10 HPMCAS ASD and a solvent-shift solution both peaked at ≈10.7 µg/mL, and the fluorescence ratio fell to the amorphous-solubility level near 180-210 min in both. At 100, 200 and 500 µg/mL ASD dose, the receiver maximum rose ≈9.2 → ≈10.0 → ≈12.2 µg/mL and its decline slowed.

Fig. 7: Solvent-shift vs ASD-derived nanodroplets
Fig. 7 · p.21 · Solvent-shift vs ASD-derived nanodropletsShows. (a) overlapping receiver profiles; (b) the fluorescence ratio falls at the same rate for both and reaches the dashed amorphous-solubility level near 180-210 min.Also supports K5
More detail

Over 240 min the two receiver curves overlapped for the first ≈50 min; later the ASD curve ran slightly higher (≈9.9 vs ≈9.3 µg/mL at 100 min, ≈7.9 vs ≈7.4 at 240 min). The fluorescence ratio stayed ≈1.15-1.22 for 60 min, then fell to ≈0.75 at 150 min and ≈0.45 at 210 min for both routes, crossing the ≈0.59 amorphous-solubility level near 180 min. The authors read this as gradual depletion of the droplets as free drug crosses the membrane, at a similar rate for both routes, and see no significant difference in absorption despite the larger ASD-derived droplets. ·· For the dose series, the donor fell from ≈90 to ≈47 µg/mL (100 µg/mL dose), from ≈195 to ≈127 (200) and from ≈510 to ≈455 (500) over 120 min, and the receiver ended at ≈6.1, ≈8.5 and ≈10.3 µg/mL. Although free drug should be the same at all three doses, Cmax rose with dose as in the solution runs; the authors attribute the more sustained transport to more droplets ("can be attributed") and suggest that Cmax "can potentially" depend on the number of droplets flowing through the module. · The solvent-shift concentration for Fig. 7 is not stated, and the polymer concentration differs between solution and ASD runs. ·

Fig. 8: ASD dose series
Fig. 8 · p.22 · ASD dose seriesShows. a higher dose of 90:10 HPMCAS:ATZ gives higher and more sustained receiver concentrations.Also supports K2
6

The absorptive sink increases release from slow ASDs and changes the polymer ranking

At 120 min the 50% loading ASDs had released ≈6200 vs ≈4200 µg (HPMCAS), ≈6300 vs ≈4600 µg (HPMC) and ≈5000 vs ≈3600 µg (PVPVA) with vs without absorption. The closed test favoured HPMC; with absorption all three released at a similar rate over the first 60 min. ·

Fig. 9: Release from 50% loading ASDs with and without absorption
Fig. 9 · p.27 · Release from 50% loading ASDs with and without absorptionShows. red (with absorption) ends above black (closed) for all three polymers.Also supports K7
More detail

With absorption, total release was counted as drug in the donor plus drug transferred. The curves overlap at first; the absorptive one pulls ahead after ≈40 min for HPMCAS and ≈50 min for HPMC, and is higher throughout for PVPVA. At 60 min the closed test gave ≈4200 (HPMC), ≈3000 (HPMCAS) and ≈2900 µg (PVPVA), and the absorptive test ≈4400, ≈3900 and ≈4100 µg. The authors conclude that the absorption compartment "clearly influenced" dissolution of slow-releasing ASDs, because removing drug lowered the donor concentration and so promoted dissolution, which better reflects in vivo conditions; the declining donor concentration is "potentially more in vivo relevant" than a closed-vessel plateau. ·· The absorptive totals rest on AUC × flow, and the apparatus mass balance does not close in the extractor's check.

04Further observations

  • PVPVA solvent-shift droplets agglomerate: ≈245 nm at the start, ≈700 nm at 75 min, ≈10 µm at 105 min.
  • Over 4 h, the 10% loading cellulose ASDs kept the receiver above the amorphous-solubility level to ≈200 min, the PVPVA one only to ≈150 min.
  • The 70:30 ASDs stayed near or below the amorphous solubility; their receivers plateaued at ≈6.0-7.7 µg/mL. ··
  • All nine ASDs were X-ray amorphous; 5-10% of the drug stayed in the apparatus until the wash. ·
More detail
  • PVPVA droplets agglomerate. In a 200 µg/mL solvent-shift solution with 1 mg/mL PVPVA, DLS size was ≈245-290 nm for the first 60 min (PDI ≈0.09-0.33), then ≈700 nm at 75 min, ≈455 nm at 90 min and ≈10 µm at 105 min (PDI up to ≈0.57); the text adds that the count rate fell. With HPMCAS or HPMC, solvent-shift droplets were 221 and 311 nm with PDI 0.07-0.1, and fluorescence ratios of 1.21-1.25 suggested a similar droplet mass for all three polymers. ···
  • Nanodroplets outlast agglomerates over 4 h. The 90:10 HPMCAS and HPMC donors fell from ≈205 µg/mL to ≈78 and ≈56 µg/mL by about 240 min, reaching the amorphous solubility after c.a. 200 min, and their receivers stayed above the amorphous-solubility level until then. The 90:10 PVPVA donor held ≈100 µg/mL to ≈120 min and its receiver ≈9.3 µg/mL to ≈110 min, then fell to ≈4.4 µg/mL by 240 min. The authors call the 2 h difference "not significant" and conclude that nanodroplets give a longer reservoir and higher AUC than agglomerated amorphous solid; they "speculate" that the PVPVA reservoir runs short of agglomerates. ····
  • Intermediate loading. The 70:30 ASDs never formed droplets: donor ≈70-78 µg/mL (HPMCAS, HPMC) and ≈74-82 µg/mL (PVPVA), receivers ≈6.0, ≈7.4 and ≈7.7 µg/mL. ····
  • Solid state and apparatus. PXRD showed halos for all nine ASDs; one narrow reflection near ≈38.7° 2θ in the 70:30 PVPVA pattern is not discussed. About 5-10% of ATZ was recovered from the methanol wash after each run. ··

05How the authors connect the findings

1Above the amorphous solubility, nanodroplets coexist with free drug fixed at the amorphous solubility, so the thermodynamic driving force stops rising. ·
↓
2The ≈200 nm droplets cannot cross the 15 nm membrane, yet transfer kept rising with their number; the authors infer a higher mass transfer coefficient. ··
↓
3The droplets also replenish free drug as it is absorbed, a reservoir that lasts longer with more droplets. ·
↓
Low drug loading, cellulose polymerFast dissolution above the amorphous solubility↓LLPS↓nanodroplets↓reservoir plus faster transfer↓highest AUC.·
Low drug loading, PVPVAFast dissolution slightly above a raised amorphous solubility↓agglomerates↓reservoir over 2 h↓runs short by ≈150 min.··
High drug loading (30-50%)Slow dissolution below the amorphous solubility↓no droplets↓lower AUC; the 50:50 PVPVA ASD crystallizes↓least transfer.··
What sets the switch point. Whether the ASD dissolves fast enough to pass the amorphous solubility, which depends on drug loading and polymer. ·
Conclusion drawn. Formulations that undergo LLPS "may enhance absorption behavior not only by providing a reservoir" but also through higher mass transfer coefficients.
More detail
  1. Free, unionized drug is the species that crosses the membrane by passive diffusion, and its driving force is the chemical potential difference. Above the amorphous solubility, drug-rich and water-rich phases share one activity, so free drug stays at the amorphous solubility, and a side-by-side cell "would typically" show a single maximum. ···
  2. In the hollow-fiber apparatus Cmax and AUC kept rising with donor concentration above the amorphous solubility, with a smaller slope. The droplets (≈200 nm) are too large for the 15 nm pores, and their own contribution to diffusivity is "expected to be negligible", so the change in proportionality "indicates a change in the mass transfer coefficient", and "logically" the rising droplet number drives it. How it works is not settled: nanoscale convection in the laminar boundary layer ("Possibly"), absorption limited by dissolution that more droplet surface relieves ("Alternatively"), or higher solubility of droplets shrinking to a few nanometres during the ≈10 s pass ("it is plausible"). ·······
  3. Absorption removes free drug and the droplets dissolve to restore the amorphous solubility; the fluorescence ratio falls as they are used up, at the same rate for ASD-derived and solvent-shift droplets. A higher dose gives more droplets and a longer plateau. ···

Low drug loading, cellulose polymer. The 90:10 HPMCAS and HPMC ASDs dissolve within minutes far above the amorphous solubility → LLPS gives ≈300 nm droplets → the receiver stays above the amorphous-solubility level for 120 min and, over 4 h, to ≈200 min → highest AUC. ···

Low drug loading, PVPVA. The 90:10 PVPVA ASD dissolves fast but PVPVA raises the amorphous solubility to 94 µg/mL, and droplets formed in the boundary layer agglomerate ("Most likely") → micron-sized agglomerates act as a reservoir over 2 h, with nearly the same transfer as the cellulose ASDs → the reservoir runs short after ≈150 min ("We speculate"). ····

High drug loading (30-50%). These ASDs dissolve slowly, "in some instances" thought to reflect a drug-rich surface layer, and stay at or below the amorphous solubility → no droplets → lower Cmax and AUC; the 50:50 PVPVA ASD crystallizes in the donor from ≈80 min → least transfer. ···

What sets the switch point. Supersaturation from ASD dissolution depends on drug loading and polymer; only when an ASD dissolves past the amorphous solubility do droplets form and add to transfer. ·

Conclusion drawn. "Formulations undergoing LLPS may enhance absorption behavior not only by providing a reservoir and replenishing drug lost due to absorption, but also by contributing to enhancements in the mass transfer coefficients"; the in vivo relevance "needs further investigation". ·

06What it means for formulation

Stated by the authors
  • Test formulations with an absorptive compartment: dissolution profiles alone can misjudge performance and the ranking of polymers. ··
  • If colloid-enhanced transfer occurs in vivo, assess colloid formation in vitro when choosing a formulation.
AI reading, not stated in the paper
  • For atazanavir at a 200 µg/mL dose, only 10% loading ASDs passed the amorphous solubility; the useful loading window here is narrow.
  • A UV concentration above the amorphous solubility mixes droplets and free drug and can exceed the dose; it is not a measure of absorbable drug.
More detail
Stated by the authors
  • Low drug loading ASDs that dissolve above the amorphous solubility and form nanodroplets give an absorption advantage over higher loadings ("clearly shows").
  • Absorption profiles "did not always concur" with conclusions drawn from dissolution profiles; the agglomerating 10% PVPVA ASD transferred nearly as much as the cellulose ASDs over 2 h, which its dissolution profile would not predict. ·
  • Including an absorptive compartment gives "a more meaningful comparison between different formulations" and a more realistic measurement of dissolution under non-sink conditions; the declining donor concentration is "potentially more in vivo relevant". ··
  • If colloid-enhanced transfer occurs in vivo ("if this occurs in vivo"), formulations should be chosen to optimize colloid formation.
  • Membrane transport of highly supersaturated solutions must be measured over biorelevant times with a fast enough mass transfer rate, because they risk crystallization. ·
AI reading, not stated in the paper
  • Within this set, nanodroplet formation, not polymer type as such, separated the best ASDs from the rest; the polymer mattered through the amorphous solubility it gives and through droplet agglomeration.
  • Agglomerating systems can look as good as droplet-forming ones in a 2 h test and fall behind later; the test duration should cover the absorption window of interest.
  • Closed-vessel ranking at high loading (HPMC best) disappeared with an absorptive sink; screening slow-releasing ASDs only in closed vessels may pick the wrong polymer.
  • Above the amorphous solubility, adding more drug as droplets still increased transfer in this apparatus; the size of that gain in vivo is not known.

07Open questions

Raised by the authors
  • Which mechanism raises transfer above the amorphous solubility: boundary-layer convection, dissolution-limited absorption, or size-dependent droplet solubility? ···
  • Does the effect occur in vivo? ·
Not covered by this paper (AI reading)
  • Free drug in the donor was not measured, so the change in mass transfer coefficient is inferred.
  • Absolute amounts from the receiver AUC do not close the mass balance.
More detail
Raised by the authors
  • A systematic study of how colloids change flow and the concentration gradient in the laminar boundary layer is "required", and nanodroplet dissolution kinetics "may shed light" on the mechanism.
  • Whether the higher mass transfer coefficient with droplets matters in vivo "needs further investigation"; the authors cite one in vivo study suggesting colloids help absorption. ·
Not covered by this paper (AI reading)
  • Free drug in the donor during transfer was not measured, so "free drug equals the amorphous solubility" at every dose and the change in mass transfer coefficient remain inferences.
  • Droplet number was counted only up to 150 µg/mL; above it, number is inferred from fluorescence and DLS count rate.
  • Receiver AUC × flow gives amounts that, by the extractor's arithmetic, exceed what the donor can supply in two cases; amounts are best read as relative.
  • Replicate numbers are not stated, one drug, one membrane type and one buffer were used, and the polymer concentration differed between solution and ASD runs. ·

08How solid

AI assessment, not a statement made in the paper
Moderate

The concentration-transfer data and the ranking of the ASDs are direct and agree between solution and ASD routes. ·· The central interpretation, a mass transfer coefficient that grows with droplet number, is inferred without free drug or droplet counts above 150 µg/mL, replicate numbers are not stated, and the absolute amounts do not close in mass balance. ···

More detail
What holds
  • The slope break at the amorphous solubility appears in both Cmax and AUC over nine concentrations, and the printed AUC fits reproduce the plotted points. ··
  • Nanodroplet formation is shown by three methods (fluorescence, DLS, NTA) with consistent onset near 75-100 µg/mL. ··
  • ASD-derived and solvent-shift droplets give overlapping receiver profiles and the same depletion rate, so the ASD findings rest on the solution data.
  • The ASD ranking (10% cellulose highest, 50:50 PVPVA lowest) follows from both receiver profiles and AUC, and crystallization is shown by microscopy. ··
What weakens it
  • Free drug and the mass transfer coefficient were not measured; three candidate mechanisms are offered and none tested. ···
  • Droplet counts stop at 150 µg/mL while transfer data reach 500 µg/mL.
  • Replicate numbers and error types are not stated except for Table 1, and no statistical tests are reported; the paper calls the 10% PVPVA vs cellulose difference both "clearly" higher and "not significant". ·
  • The printed above-AS Cmax fit does not reproduce its points, Fig. 6G plots AUC under an "amount" caption, and receiver AUC × flow does not close the mass balance. ··
  • UV apparent concentrations above the amorphous solubility include scattering and exceed the dose; amorphous-solubility lines differ between figures, and the HPMC line has no measured basis. ·
  • The polymer concentration differs between the solvent-shift solutions and the ASD runs.

09Figure guide

Every figure and table of the paper, what it is there for, and what to check on the original. Key figures are shown with the story.

FigureWhat it does in the paperSupportsCheck (AI note)
Fig. 1 (p.10)key figureDetects LLPS: the fluorescence ratio rises above ≈0.6 once the amorphous solubility is passed.F1
Table 1 (p.10-11)Droplet size stays 204-226 nm from 100 to 500 µg/mL while the count rate rises.F1, K2
Fig. 2 (p.11-12)key figureCounts droplets: number roughly doubles per step from 75 to 150 µg/mL.F1, K2Counts stop at 150 µg/mL.
Fig. 3 (p.13)key figureReceiver profiles for nine solution concentrations, with the amorphous-solubility reference line.F2The reference line sits above the measured Cmax at 75 µg/mL.
Fig. 4 (p.14)key figureThe key evidence: Cmax and AUC keep rising above the amorphous solubility, with a slope break.F2, K1, K3The printed above-AS Cmax fit does not match its points.
Fig. 5 (p.16)key figureClosed dissolution: only the 90:10 ASDs exceed the amorphous solubility.F3Apparent values above the amorphous solubility include scattering; HPMC line unexplained.·
Fig. 6 (p.19)key figureDissolution-absorption of all nine ASDs and the AUC ranking.·F4, K4Panel G plots AUC under an "amount" caption.
Table 2 (p.20)Droplet properties from solvent shift and from 90:10 ASDs, with and without absorption.F3, K5Text gives 350 nm for HPMC, table 311 nm.
Fig. 7 (p.21)key figureASD-derived and solvent-shift droplets give the same receiver profile and depletion.F5, K5Solvent-shift concentration not stated.
Fig. 8 (p.22)key figureHigher ASD dose sustains transfer longer.F5, K2Cited as Figure 6 in the Discussion; mass balance at 100 µg/mL does not close.·
Fig. 9 (p.27)key figureThe absorptive sink increases release from all 50% loading ASDs.F6, K7Totals rest on AUC × flow.
TOC graphic (p.33)Summary schematic of the paper's message.headerA schematic, not data.
More detail
FigureWhat it does in the paperSupportsCheck (AI note)
Fig. S1 (SI p.1)Emission spectra below and above the amorphous solubility, showing the 369 nm band.F1
Fig. S2 (SI p.2)PXRD: the nine ASDs are X-ray amorphous.0.4One narrow reflection in 70:30 PVPVA not discussed.
Fig. S3 (SI p.2-3)Crystals in the 50:50 PVPVA donor at 100 min.F4Caption mentions "lower images" not shown as such.
Fig. S4 (SI p.3)PVPVA solvent-shift droplets agglomerate over 105 min.F3, 0.4
Fig. S5 (SI p.4)50% loading ASDs compared by polymer, closed vs absorptive.F6, K8
Fig. S6 (SI p.5)Over 4 h, cellulose ASD droplets outlast PVPVA agglomerates.K6, 0.44 h AUC values not printed.