In silico estimation of DMSO solubility of organic compounds for bioscreening

Journal of Biomolecular Screening

Volumn 9, Issue 1, 2004, Pages 22-31

  Balakin, Konstantin V ^a   Ivanenkov, Yan A ^a   Skorenko, Andrey V ^a   Nikolsky, Yuri V ^a   Savchuk, Nikolay P ^a   Ivashchenko, Andrey A ^a  

^a CHEMDIV INC   (United States)

Author keywords

DMSO; Kohonen self organizing maps; Neural networks; Quantitative structure property relationship; Solubility

Indexed keywords

DIMETHYL SULFOXIDE; ORGANIC COMPOUND;

ARTICLE; ARTIFICIAL NEURAL NETWORK; COMPUTER MODEL; DRUG STORAGE; ENERGY; FEEDBACK SYSTEM; LIPOPHILICITY; MAGNETISM; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SOLUBILITY; SOLVATION; CHEMISTRY; STRUCTURE ACTIVITY RELATION;

DIMETHYL SULFOXIDE; NEURAL NETWORKS (COMPUTER); ORGANIC CHEMICALS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4544285614     PISSN: 10870571     EISSN: None     Source Type: Journal    
DOI: 10.1177/1087057103260006     Document Type: Article

References (32)

1. Budavari S: The Merck Index: Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., 1989.
2. Brown JH: Double-blind clinical study: DMSO for acute injuries and inflammations compared to accepted standard therapy. Curr Ther Res 1971;13:536-540.
3. Small A, Ide RS: Failure to detect nephrotoxicity of chronically administered dimethyl sulfoxide (DMSO) in rats. Cryobiology 1976;13:328-333.
4. Raegnier JF, Richard J: Lack of developmental toxicity in rats treated with dimethyl sulfoxide (DMSO). Toxicologist 1998;42:256-257.
5. Murdoch LA: Dimethyl sulfoxide (DMSO): overview. Can J Hosp Pharm 1982;35:79-85.
6. Hagelman RF, Evans TC, Riley EF: Modification of radiation effect on eye by topical application of dimethyl sulfoxide. Radiat Res 1970;44:368-342.
7. Wood DC, Wood J: Pharmacologic and biochemical considerations of dimethyl sulfoxide. Ann NY Acad Sci 1975;243:7-19.
8. Lowelock JE, Bishop MWH: Prevention of freezing damage to living cells by dimethyl sulphoxide. Nature 1979;183:1394-1395.
9. Hochlowski J, Cheng X, Sauer D, Djuric S: Studies of the relative stability of TFA adducts vs non-TFA analogues for combinatorial chemistry library members in DMSO in a repository compound collection. J Comb Chem 2003;5:345-350.
10. Kozikowski BA: The effect of freeze/thaw cycles on the stability of compounds in DMSO. Paper presented at the 7th Annual SBS Conference and Exhibition, Baltimore, September 2001.
11. Turmel M, Spreen R, Nie D: Preliminary investigation of compound stability under various storage conditions. Paper presented at the Drug Discovery Congress, Boston, August 2002.
12. Beckner C, Cheng X, Hepp D: Studies on compound stability in DMSO under different conditions. Paper presented at the Drug Discovery Congress, Boston, August 2002.
13. Yaskanin D: Quality perspectives for compound storage. Paper presented at the Automated Compound Storage & Retrieval Meeting, Somerset, UK, January 2003.
14. Fillers WS: Key factors affecting compound integrity. Paper presented at the LabAutomation Meeting, Palm Springs, CA, February 2003.
15. Lipinski CA: Storage of samples in DMSO: issues and potential solutions. Paper presented at the SBS 8th Annual Conference and Exhibition, Hague, The Netherlands, September 2002.
16. Gaylord Chemical Corp.: Solubility of active pharmaceutical compounds (APCs) in USP grade dimethyl sulphoxide (DMSO) [Online]. Retrieved from http://www.gaylordchemical.com/bulletins/PharmaSolubilities% 20booklet%20bulletin.pdf
17. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ: Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 1997;23:3-25.
18. Raevsky OA, Trepalin SV, Trepalina HP, Gerasimenko VA, Raevskaya OE: SLIPPER-2001: software for predicting molecular properties on the basis of physicochemical descriptors and structural similarity. J Chem Inf Comput Sci 2002;42:540-549.
19. Scarsi M, Apostolakis J, Caflisch A: Comparison of a GB solvation model with explicit solvent simulations: potentials of mean force and conformational preferences of alanine dipeptide and 1,2-dichloroethane. J Phys Chem B 1998;102:3637-3641.
20. Song X, Chandler D: Dielectric solvation dynamics of molecules of arbitrary shape and charge distribution. J Chem Phys 1998;108:2594-2600.
21. Cui Q: Combining implicit solvation models with hybrid quantum mechanical molecular mechanical methods: a critical test with glycine. J Chem Phys 2002;117:4720-4728.
22. Jensen L, van Duijnen PT, Snijders JG: A discrete solvent reaction field model within density functional theory. J Chem Phys 2003;118:514-521.
23. Pierotti RA: A scaled particle theory of aqueous and nonaqueous solutions. Chem Rev 1976;76:717-726.
24. Mezei M, Beveridge DL: Free energy simulations. Ann Acad Sci NY 1986;482:1-23.
25. Straatsma TP, McCammon JA: Computational alchemy. Annu Rev Phys Chem 1992;43:407-435.
26. Sadowski J, Kubinyi H: A scoring scheme for discriminating between drugs and nondrugs. J Med Chem 1998;41:3325-3329.
27. Ajay A, Walters WP, Murcko MA: Can we learn to distinguish between "drug-like" and "nondrug-like" molecules? J Med Chem 1998;41:3314-3324.
28. Balakin KV, Tkachenko SE, Lang SA, Okun I, Ivashchenko AI, Savchuk NP: Property-based design of GPCR-targeted library. J Chem Inf Comput Sci 2002;42:1332-1342.
29. Lang SA, Kozyukov AV, Balakin KV, Skorenko AV, Ivashchenko AA, Savchuk NP: Classification scheme for the design of serine protease targeted compound libraries. J Comp-Aid Mol Des 2002;16:803-807.
30. Anzali S, Gasteiger J, Holzgrabe U, et al: The use of self-organizing neural networks in drug design. In Kubinyi H, Folkers G, Martin YC (eds): 3D QSAR in Drug Design: Volume 2. Dordrecht, The Netherlands: Kluwer/ESCOM, 1998:273-299.
31. Brüstle M, Beck B, Schindler T, King W, Mitchell T, Clark T: Descriptors, physical properties, and drug-likeness. J Med Chem 2002;45:3345-3355.
32. Nikolsky Y, Balakin KV, Ivanenkov YA, Ivashchenko AA, Savchuk NP: Intelligent machine learning technologies in pre-synthetic combinatorial design. Pharma Chem 2003;4:68-72.