DMSO solubility

Balakin KV, Ivanenkov YA, Skorenko AV, Nikolsky YV, Savchuk NP, Ivashchenko AA. In silico estimation of DMSO solubility of organic compounds for bioscreening. J Biomol Scr 2004 9 22-31. 

Acids consistently display low solubility in DMSO. In our Pfizer studies we found acids to be 4 times more likely to have poor DMSO solubility of less than 5pgmL than any other functionality. The reason is that DMSO with its very electronegative oxygens is a poor solvator for any compound with partial negative or full anionic character. 

Where Does Poor DMSO Solubility Come From ... 

I. V. In silica approaches to prediction of aqueous and DMSO solubility of druglike compounds trends, problems and solutions. Curr. Med. Chem. 2006, 13, 223-241. 

J. Lu, G. A. Bakken, Building classification models for DMSO solubility comparison of five methods, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004, CINF-045. 

Ohkoshi, M. and Kato, A. (1993). Determination of substituent distribution of DMSO-soluble portion of acetylated wood meal by C-NMR spechoscopy. Mokuzai Gakkaishi, 39(7), 849-854. 

Balakin, K.V. 2003. DMSO solubility and bioscreening. Curr. Drug Disc. 8, 27-30. 

Polymeric carbon nanocomposites are often functionalized with matrix polymers. An example is the functionalization of SWNTs and MWNTs with poly(vinyl alcohol) using a carbodiimide mediated esterification reaction. Also, poly(ethylene-co-vinyl alcohol) is used for this purpose to produce DMSO soluble functionalized SWNTs. In a similar manner poly(m-aminobenzene sulfonic acid) is covalently bonded to SWNTs to form water soluble graft copolymers. ... 

Embery, G. and Dugrad, P. H. The isolation of DMSO soluble components from human epidermis preparations A possible mechanism of action of dimethylsulf-oxide in effecting percutaneous migration phenomena. Journal of Investigative Dermatology 57 308-311, 1971. 

In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds trends, problems and solutions. Current Medicinal Chemistry, 13 (2), 223-241 Meltzer, P.S., Kallioniemi, A. and Trent, J.M. (2002) Chromosome alterations in human solid tumors, in The Genetic Basis of Human Cancer (eds B. Vogelstein and K.W. Kinzler), McGraw-Hill, New York, pp. 93-113. 

Solubility in DMSO is less intuitive than aqueous solubility, based on examination of the chemical structure. Chemists can usually differentiate between compounds that are soluble or insoluble in water, but it is much harder to predict compounds that are soluble or insoluble in DMSO (Balakin, 2003). Solubility in DMSO is determined by a subtle balance of oppositely-directed inter- and intramolecular forces. Computational models have been developed to predict DMSO solubility with greater than a 90% success rate (Balakin, 2003 Balakin et al., 2004 Japertas et al., 2004 Lu and Bakken, 2004 Delaney, 2005). Software can be used to provide an alert to a compound with a low DMSO solubility... 

Other Approaches to Increase Aqueous Solubility Strategies used to improve DMSO solubility can also be applied to increase aqueous solubility. In-well sonication and screening at a lower concentration (e.g., 3 pM vs. 10 pM), help to minimize precipitation. 

Balakin KV. DMSO Solubility and Bioscreening. Curr Drug Discov 2003 27-30. 

Japertas P, Verheij H, and Petrauskas A. DMSO Solubility Prediction. LogP 2004, Zurich, Switzerland, 2004. 

---