In Silico Estimation of DMSO Solubility of Organic Compounds for Bioscreening

Balakin, Konstantin V.; Ivanenkov, Yan A.; Skorenko, Andrey V.; Nikolsky, Yuri; Savchuk, Nikolay P.; Ivashchenko, A. V.

doi:10.1177/1087057103260006

Cited by 61 publications

(50 citation statements)

References 22 publications

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“…There were several studies, in which large databases with binary experimental DMSO solubility data were used. Balakin et al used 65,500 compounds from ChemDiv's corporate collection [127]. A total of 55,277 compounds with DMSO solubility at room temperature higher than 10 mM were considered DMSO well-soluble, and 10,223 compounds with DMSO solubility at 40 °C less than 10 mM as DMSO poorly soluble.…”

Section: Dmso Solubility Data Sourcesmentioning

confidence: 99%

In Silico Approaches to Prediction of Aqueous and DMSO Solubility of Drug-Like Compounds: Trends, Problems and Solutions

Balakin

Savchuk²,

Tetko³

2006

CMC

164

113

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The solubility of drugs and drug-like compounds has been the subject of extensive studies aimed at finding a way to predict solubility from molecular structure. The aqueous solubility of a drug is an important factor that influences its absorption, distribution and elimination in the body. Poor aqueous solubility often causes a drug to appear inactive and may cause other biological problems. Compound solubility in DMSO represents another serious problem in early stages of drug discovery. An appreciation of the factors affecting a compound's DMSO solubility could help in predicting the storage conditions and appropriateness of compounds for primary bioscreening programs. In silico procedures for estimation of water and DMSO solubility represent extremely useful tools for the drug discovery practitioners. In this review, we provide a critical discussion of in silico models for the prediction of DMSO and water solubility of drug-like compounds used for virtual screening. We describe the main tendencies in the field, "booming" approaches and unsolved problems. A critical analysis of the accuracy and applicability of methods is provided.

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Section: Dmso Solubility Data Sourcesmentioning

confidence: 99%

In Silico Approaches to Prediction of Aqueous and DMSO Solubility of Drug-Like Compounds: Trends, Problems and Solutions

Balakin

Savchuk²,

Tetko³

2006

CMC

164

113

View full text Add to dashboard Cite

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“…Poor aqueous solubility is a serious drawback when dealing with druglike molecules rather than with real drugs; this problem cannot be circumvented because of the lack of experimental or reliable calculated values of aqueous solubility for most of the compounds filed in the currently employed databases. 38 Cytotoxicity of Selected Heterocyclic Compounds. The evaluation of the selected small molecules as potential anti-AD agents was performed by means of the pharmacological predictive in vitro model set up in this study.…”

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confidence: 99%

p53 Functional Inhibitors Behaving Like Pifithrin-β Counteract the Alzheimer Peptide Non-β-amyloid Component Effects in Human SH-SY5Y Cells

Pozzo

Pietra

Cosimelli

et al. 2014

ACS Chem. Neurosci.

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Alzheimer's disease (AD) develops from a complex setting of genetic and biochemical alterations, including an increased level of p53 in the brain. Here, the robust and specific activation of p53 by the fibrillar non-β-amyloid component (NAC) of AD was demonstrated in human neuroblastoma SH-SY5Y cells. For the first time, the increase in the level of p53 target gene transcription, the cell cycle arrest, and the induction of apoptosis elicited by NAC were evidenced. These effects were counterbalanced by pifithrin-β, a small molecule interfering with the p53 functions. Using the structure of a pifithrin-β analogue as a reference, a pharmacophore-based virtual screening of the ZINC database was performed. Among the resulting hits, 20 druglike heterocyclic compounds were selected and evaluated for their neuroprotective activity against fibrillar NAC in the human SH-SY5Y cellular model. Three compounds exhibited neuroprotective effects. In particular, 2-(4-methoxyphenyl)-7-methyl-7H-pyrazolo [4,3-e][1,2,4]triazolo [1,5-c]pyrimidine resulted in a promising lead compound for further development of anti-AD agents in terms of neuroprotection, reducing the rate of NAC-induced cell death with an activity higher than that of pifithrin-β, as a result of a more effective functional inhibition of p53 target gene transcription.

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“…To avoid this, 200 µL of DMSO, a low-volatility solvent (boiling point 189°C), was added to the tube before the evaporation. Moreover, DMSO is a versatile aprotic solvent able of dissolving both hydrophobic and hydrophilic compounds [53]. The gain obtained in terms of recovery in the presence of DMSO is illustrated in Figure 5.…”

Section: Addition Of Dmso Before the Evaporation Stepmentioning

confidence: 99%

Trace-level determination of pyrethroid, neonicotinoid and carboxamide pesticides in beeswax using dispersive solid-phase extraction followed by ultra-high-performance liquid chromatography-tandem mass spectrometry

Jabot

Fieu

Giroud

et al. 2015

International Journal of Environmental Analytical Chemistry

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International audienceThe aim of the work was to develop an analytical procedure able to quantify traces of 13 neonicotinoids and pyrethroids as well as carboxamide in beeswax at low levels (ng g(-1)) to evaluate the contamination. For this purpose, an efficient sample preparation procedure was developed based on solid-liquid extraction using dispersive diatomaceous earth and acetonitrile. This step was followed by a selective and sensitive analysis based on ultra-high-performance liquid chromatography coupled to tandem mass spectrometry (ESI-MS/MS). This analytical procedure was validated based on International Conference on Harmonization guidelines. The limits of quantification ranged from 1ngg(-1) (thiamethoxam, clothianidin, imidacloprid, acetamiprid, thiacloprid and boscalid) to 40ngg(-1) (lambda-cyhalothrin). The method was then successfully applied to 60 samples of beeswax collected in several areas of France. The presence of thiacloprid, boscalid, imidacloprid and deltamethrin in beeswax was confirmed. The most frequently quantified pesticide was boscalid

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In Silico Estimation of DMSO Solubility of Organic Compounds for Bioscreening

Cited by 61 publications

References 22 publications

In Silico Approaches to Prediction of Aqueous and DMSO Solubility of Drug-Like Compounds: Trends, Problems and Solutions

In Silico Approaches to Prediction of Aqueous and DMSO Solubility of Drug-Like Compounds: Trends, Problems and Solutions

p53 Functional Inhibitors Behaving Like Pifithrin-β Counteract the Alzheimer Peptide Non-β-amyloid Component Effects in Human SH-SY5Y Cells

Trace-level determination of pyrethroid, neonicotinoid and carboxamide pesticides in beeswax using dispersive solid-phase extraction followed by ultra-high-performance liquid chromatography-tandem mass spectrometry

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