Development and application of an automated solution stability assay for drug discovery

Journal of Biomolecular Screening

Volumn 11, Issue 1, 2006, Pages 40-47

  Di, Li ^a,b   Kerns, Edward H ^a   Chen, Hong ^a   Petusky, Susan L ^a  

^a PFIZER INC   (United States)

^b NONE   (United States)

Author keywords

Automation; Chemical stability; High throughput; HPLC; Hydrolysis; Kinetics; LC MS; Stability; Stability pH profile

Indexed keywords

BISACODYL; THEOPHYLLINE; VINCAMINE;

ACCURACY; ARTICLE; AUTOMATION; DRUG DETERMINATION; DRUG STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HYDROLYSIS; INCUBATION TIME; PH; PRIORITY JOURNAL; REACTION TIME; TEMPERATURE;

AUTOMATION; BIOLOGICAL ASSAY; BISACODYL; BODY FLUIDS; BUFFERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; SOLUTIONS; VINCAMINE;

EID: 32844464311     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057105281363     Document Type: Article

References (34)

1. Kerns EH, Di L: Pharmaceutical profiling in drug discovery. Drug Disc Today 2003 ; 8: 316-323.
2. Kerns EH, Di L: Accelerated stability profiling in drug discovery. Log P 2004 Proceeding 2004.
3. Kibbey CE, Poole SK, Robinson E, Jackson JD, Durham D: An integrated process for measuring the physicochemical properties of drug candidates in a preclinical discovery environment. J Pharm Sci 2001 ; 90: 1164-1175.
4. Shah KP, Zhou J, Lee R, Schowen RL, Elsbernd R, Ault JM,, et al. Automated analytical systems for drug development studies. I - asystem for the determination of drug stability. J Pharm Biomed Anal 1994 ; 12: 993-1001.
5. von Rauch M, Schlenk M, Gust R: Effects of C2-alkylation, N-alkylation, and N,N'-dialkylation on the stability and estrogen receptor interaction of (4R,5S)/ (4S,5R)-4,5-Bis(4-hydroxyphenyl)-2-imidazolines. J Med Chem 2004 ; 47: 915-927.
6. Magnin DR, Robl JA, Sulsky RB, Augeri DJ, Huang Y, Simpkins LM,, et al. Synthesis of novel potent dipeptidyl peptidase IV inhibitors with enhanced chemical stability: interplay between the N-terminal amino acid alkyl side chain and the cyclopropyl group of α-aminoacyl-L-cis-4,5-methanoprolinenitrile- based inhibitors. J Med Chem 2004 ; 47: 2587-2598.
7. Chang CWT, Hui Y, Elchert B, Wang J, Li J, Rai R: Pyranmycins, a novel class of aminoglycosides with improved acid stability: the SAR of Dpyranoses on ring III of pyranmycin. Org Lett 2002 ; 4: 4603-4606.
8. Regueiro-Ren A, Leavitt K, Kim SH, Hofle G, Kiffe M, Gougoutas JZ,, et al. SAR and pH stability of cyano-substituted epothilones. Org Lett 2002 ; 4: 3815-3818.
9. Posner GH, Paik IH, Sur S, McRiner AJ, Borstnik K, Xie S,, et al. Orally active, antimalarial, anticancer, artemisinin-derived trioxane dimers with high stability and efficacy. J Med Chem 2003 ; 46: 1060-1065.
10. Chong Y, Gumina G, Mathew JS, Schinazi RF, Chu CK: L-2',3'-didehydro-2', 3'-dideoxy-3'-fluoronucleosides: synthesis, anti-HIV activity, chemical and enzymatic stability, and mechanism of resistance. J Med Chem 2003 ; 46: 3245-3256.
11. Guilford WJ, Bauman JG, Skuballa W, Bauer S, Wei GP, Davey D,, et al. Novel 3-oxa lipoxin A4 analogueswith enhanced chemical andmetabolic stability have anti-inflammatory activity in vivo. J Med Chem 2004 ; 47: 2157-2165.
12. Jung M, Lee K, Kendrick H, Robinson BL, Croft SL: Synthesis, stability, and antimalarial activity of new hydrolytically stable and water-soluble (+)deoxoartelinic acid. J Med Chem 2002 ; 45: 4940-4944.
13. Akers MJ: Excipient-drug interactions in parenteral formulations. J Pharm Sci 2002 ; 91: 2283-2300.
14. Jonkman-De Vries JD, Doppenberg WG, Henrar REC, Bult A, Beijnen JH: Systematic study on the chemical stability of the prodrug antitumor agent carzelesin (U-80,244). J Pharm Sci 1996 ; 85: 1227-1233.
15. Bonina FP, Arenare L, Palagiano F, Saija A, Nava F, Trombetta D,, et al. Synthesis, stability, and pharmacological evaluation of nipecotic acid prodrug. J Pharm Sci 1999 ; 88: 561-567.
16. Vabeno J, Nielsen CU, Ingebrigtsen T, Lejon T, Steffansen B, Luthman K: Dipeptidomimetic ketomethylene isosteres as pro-moieties for drug transport via the human intestinal di-/tripeptide transporter hPEPT1: design, synthesis, stability, and biological investigations. J Med Chem 2004 ; 47: 4755-4765.
17. Di L, Kerns EH, Hong Y, Kleintop TA, McConnell OJ, Huryn DM: Optimization of a higher throughput microsomal stability screening assay for profiling drug discovery candidates. J Biomol Screen 2003 ; 8: 453-462.
18. Di L, Kerns EH, Gao N, Li SQ, Huang Y, Bourassa JL,, et al. Experimental design on single-time-point high-throughput microsomal stability assay. J Pharm Sci 2004 ; 93: 1537-1544.
19. Di L, Kerns EH, Hong Y, Chen H: Development and application of high throughput plasma stability assay for drug discovery. Int J Pharm 2005 ; 297: 110-119.
20. Clapton SD, Anand BS, Mitra AK: Effect of mono-and di-acylation on the ocular disposition of ganciclovir: physicochemical properties, ocular bioreversion, and antiviral activity of short chain ester prodrugs. J Pharm Sci 2002 ; 91: 660-668.
21. Patel P, Osechinskiy S, Koehler J, Zhang L, Vajjhala S, Philips C,, et al. Micro parallel liquid chromatography for high-throughput compound purity analysis and early ADMET profiling. J Assoc Lab Automation 2004 ; 9: 185-191.
22. Kyranos JN, Cai H, Wei D, Goetzinger WK: High-throughput highperformance liquid chromatography/mass spectrometry for modern drug discovery. Curr Opin Biotechnol 2001 ; 12: 105-111.
23. Kyranos JN, Lee H, Goetzinger WK, Li LYT: One-minute full-gradient HPLC/UV/ELSD/MS analysis to support high-throughput parallel synthesis. J Comb Chem 2004 ; 6: 796-804.
24. Lai F, Khojasteh-Bakht SC: Automated online liquid chromatographic/mass spectrometric metabolic study for prodrug stability. J Chromatogr B Analyt Technol Biol 2005 ; 814: 225-232.
25. Kerns EH, Kleintop T, Little D, Tobien T, Mallis L, Di L,, et al. Integrated high capacity solid phase extraction-MS/MS system for pharmaceutical profiling in drug discovery. J Pharm Biomed Anal 2004 ; 34: 1-9.
26. Lim HK, Chan KW, Sisenwine S, Scatina JA: Simultaneous screen for microsomal stability and metabolite profile by direct injection turbulentlaminar flow LC-LC and automated tandem mass spectrometry. Anal Chem 2001 ; 73: 2140-2146.
27. Zeng H, Wu JT, Unger SE: The investigation and the use of high flowcolumnswitching LC/MS/MS as a high-throughput approach for direct plasma sample analysis of single and multiple components in pharmacokinetic studies. J Pharm Biomed Anal 2002 ; 27: 967-982.
28. Peng SX, Strojnowski MJ, Bornes DM: Direct determination of stability of protease inhibitors in plasma by HPLC with automated column-switching. J Pharm Biomed Anal 1999 ; 19: 343-349.
29. Xu R, Nemes C, Jenkins KM, Rourick RA, Kassel DB, Liu CZC: Application of parallel liquid chromatography/mass spectrometry for high throughput microsomal stability screening of compound libraries. J Am Soc Mass Spectrom 2002 ; 13: 155-165.
30. U.S. Pharmacopeia: The National Formulary (USP-NF). Rockville, MD: United States Pharmacopeial Convention, 2004.
31. Song Y, Schowen RL, Borchardt RT, Topp EM: Effect of "pH" on the rate of asparagine deamidation in polymeric formulations: "pH"-rate profile. J Pharm Sci 2001 ; 90: 141-156.
32. Fubara JO, Notari RE: Influence of pH, temperature and buffers on cefepime degradation kinetics and stability predictions in aqueous solutions. J Pharm Sci 1998 ; 87: 1572-1576.
33. Zhou M, Notari RE: Influence of pH, temperature, and buffers on the kinetics of ceftazidime degradation in aqueous solutions. J Pharm Sci 1995 ; 84: 534-538.
34. Muangsiri W, Kirsch LE: The kinetics of the alkaline degradation of daptomycin. J Pharm Sci 2001 ; 90: 1066-1075.