Solubility at the molecular level: Development of a critical aggregation concentration (CAC) assay for estimating compound monomer solubility

Pharmaceutical Research

Volumn 29, Issue 7, 2012, Pages 1745-1754

  Wang, Jie ^a   Matayoshi, Edmund ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

aggregation; confocal; drug discovery; solubility; static light scattering

Indexed keywords

FLUNARIZINE; MICONAZOLE; MICONAZOLE NITRATE; TAMOXIFEN;

ANALYTIC METHOD; AQUEOUS SOLUTION; ARTICLE; CRITICAL AGGREGATION CONCENTRATION; DRUG SOLUBILITY; LIGHT SCATTERING; MEASUREMENT; NEPHELOMETRY; PARTICLE SIZE; PREDICTION; PRIORITY JOURNAL; RELIABILITY; REPRODUCIBILITY; VALIDITY;

ANIMALS; CATTLE; DRUG DISCOVERY; HIGH-THROUGHPUT SCREENING ASSAYS; LIGHT; PHARMACEUTICAL PREPARATIONS; SCATTERING, RADIATION; SERUM ALBUMIN, BOVINE; SOLUBILITY;

EID: 84862822502     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-012-0730-8     Document Type: Article

References (34)

1. Di L, Kerns EH. Biological assay challenges from compound solubility: strategies for bioassay optimization. Drug Discovery Today. 2006;11:446-51.
2. Alsenz J, Kansy M. High throughput solubility measurement in drug discovery and development. Adv Drug Del Rev. 2007;59:546-67.
3. Feng BY, Simeonov A, Jadhav A, Babaoglu K, Inglese J, Shoichet BK, Austin CP. A high-throughput screen for aggregation-based inhibition in a large compound library. J Med Chem. 2007;50:2385-90.
4. Seidler J, McGovern SL, Doman TN, Shoichet BK. Identification and prediction of promiscuous aggregating inhibitors among known drugs. J Med Chem. 2003;46:4477-86.
5. Frenkel YV, Clark AD, Das K, Wang YH, Lewi PJ, Janssen PAJ, Arnold E. Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability. J Med Chem. 2005;48:1974-83.
6. Coan KED, Shoichet BK. Stoichiometry and physical chemistry of promiscuous aggregate-based inhibitors. J Am Chem Soc. 2008;130:9606-12.
7. McGovern SL, Caselli E, Grigorieff N, Schoichet BK. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J Med Chem. 2002;45:1712-22.
8. Rishton GM. Nonleadlikeness and leadlikeness in biochemical screening. Drug Discovery Today. 2003;8:86-96.
9. Goode DR, Totten RK, Heeres JT, Hergenrother PJ. Identification of promiscuous small molecule activators in high-throughput enzyme activation screens. J Med Chem. 2008;51:2346-9.
10. Pan L, Ho Q, Tsutsui K, Takahashi L. Comparison of chromatographic and spectroscopic methods used to rank compounds for aqueous solubility. J Pharm Sci. 2001;90:521-9.
11. Dehring KA, Workman HL, Miller KD, Mandagere A, Poole SK. Automated robotic liquid handling/laser-based nephelometry system for high throughput measurement of kinetic aqueous solubility. J Pharm Biomed Anal. 2004;36:447-56.
12. Tan H, Semin D, Wacker M, Cheetham J. An automated screening assay for determination of aqueous equilibrium solubility enabling SPR study during drug lead optimization. J Lab Autom. 2005;10:364-73.
13. Sugano K, Kato T, Suzuki K, Keiko K, Sujaku T, Mano T. High throughput solubility measurement with automated polarized light microscopy analysis. J Pharm Sci. 2006;95:2115-22.
14. Hoelke B, Gieringer S, Arit M, Saal C. Comparison of nephelometric, UV-spectroscopic, and HPLC methods for highthroughput determination of aqueous drug solubility in microtiter plates. Anal Chem. 2009;81:3165-72.
15. Heikkila T, Karjalainen M, Ojala K, Partola K, Lammert F, Augustijns P, Urtti A, Yliperttula M, Peltonen L, Hirvonen J. Equilibrium drug solubility measurements in 96-well plates reveal similar drug solubilities in phosphate buffer pH 6.8 and human intestinal fluid. Int J Pharm. 2011;405:132-6.
16. Kerns EH, Di L, Carter GT. In vitro solubility assays in drug discovery. Curr Drug Metab. 2008;9:879-85.
17. Yamashita T, Dohta Y, Nakamura T, Fukami T. High-speed solubility screening assay using ultra-performance liquid chromatography/mass spectrometry in drug discovery. J Chromatogr A. 2008;1182:72-6.
18. Bhattachar SN, Wesley JA, Seadeek C. Evaluation of the chemiluminescent nitrogen detector for solubility determinations to support drug discovery. J Pharm Biomed Anal. 2006;41:152-7.
19. Bevan CD, Lloyd RS. A high-throughput screening method for the determination of aqueous drug solubility using laser nephelometry in microtiter plates. Anal Chem. 2000;72:1781-7.
20. Goodwin JJ. Rationale and benefit of using high throughput solubility screens in drug discovery. Drug Discovery Today. 2006;3:67-71.
21. Attwood D, Fletcher P. Total intensity and quasielastic light scattering studies on the association of amphiphilic drugs in aqueous electrolyte solutions. J Coll Int Sci. 1987;115:104-9.
22. Taboada P, Attwood D, Ruso JM, Garcia M, Mosquera V. Static and dynamic light scattering study on the association of some antidepressants in aqueous electrolyte solution. Phys Chem Chem Phys. 2000;2:5175-9.
23. Pecora R. Dynamic Light Scattering: Applications of Photon Correlation Spectroscopy. New York: Plenum Press; 1985.
24. VanAken T, Foxall-VanAken S, Castleman S, Ferguson-Miller S. Alkyl glycoside detergents: synthesis and applications to the study of membrane proteins. Methods Enzymol. 1986;125:27-35.
25. Affymetrix, Inc. Anatrace 2011-2012 product catalog. Available at: http://media.affymetrix.com/support/technical/anatrace/docs/2011-12-Anatrace- products-catalog.pdf
26. Gardner CR, Walsh CT, Almarsson O. Drugs as materials: valuing physical form in drug discovery. Nat Rev Drug Discov. 2004;3:926-34.
27. Brouwers J, Brewster ME, Augustijns P. Supersaturating drug delivery system: The answer to solubility-limited oral bioavailability? J Pharm Sci. 2009;98(8):2549-71.
28. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Aqueous solubility of crystalline and amorphous drugs:Challenges in measurement. Pharm Dev Tech. 2011;16(3):187-200.
29. Baird JA, Taylor LS, Evaluation of amorphous solid dispersion properties using thermal analysis techniques. Adv Drug Deli Rev. 2011.
30. Fang H, Qiu L, Vitkin E, Zaman MM, Andersson C, Salahuddin S, Kimerer LM, Cipolloni PB, Modell MD, Turner BS, Keates SE, Bigio I, Itzkan I, Freedman SD, Bansil R, Hanlon EB, Perelman LT. Confocal light absorption and scattering spectroscopic microscopy. Appl Opt. 2007;46(10):1760-9.
31. Gao Y, Li LB, Zhai G. Preparation and characterization of Pluronic/TPGS mixed micelles for solubilization of camptothecin. Colloids Surf B. 2008;64:194-9.
32. Zimm BH. The scattering of light and the radial distribution function of high polymer solutions. J Chem Phys. 1948;16(12):1093-9.
33. Wyatt P. Light scattering and the absolute characterization of macromolecules. Anal Chimi Acta. 1993;272(193):1-40.
34. Sandison DR, Webb WW. Background rejection and signal-to-noise optimization in confocal and alternative fluorescence microscopes. Appl Opt. 1994;33(4):603-15.