Search PubMed⌕ Search

PubMed · 3971956

Solvent interactions with test compounds and recommendations for testing to avoid artifacts.

Abstract

Reports in the literature describing artifactual results owing to interactions of test materials with solvents are becoming more frequent. The present study was initiated to examine possible interactions of 1,1,3-trichloro-, 1,1,3,3-tetrachloro-, pentachloro- and hexachloroacetones with different solvents, since certain solvent effects with the last compound have been shown previously. Quantitative differences in levels of mutagenic potency were found for tri-, tetra-, and pentachloroacetone, dissolved in acetone or dimethyl sulfoxide (DMSO). On the other hand, hexachloroacetone without solvent was mutagenic, and this activity was enhanced when it was dissolved in DMSO; in acetone it was not mutagenic. A time-dependent reaction of hexachloroacetone with DMSO was the only test material-solvent interaction found in this study. The results show clearly that DMSO is not an appropriate solvent for hexachloroacetone. On the basis of these and previous results, we recommend consideration of the following strategy to help prevent reporting of artifactual results owing to interaction with solvents: Results from initial screening experiments should be confirmed in repeat experiments using a different solvent; and a different solvent should be used in confirming the findings of other investigators. Differences in results would indicate a need for further study.

Explore related subjects

Keep this discovery

Explore connections, maps & timelines

BibTeXRIS

E R Nestmann, G R Douglas, D J Kowbel, T R Harrington. 1985. Solvent interactions with test compounds and recommendations for testing to avoid artifacts.. https://doi.org/10.1002/em.2860070205

Cite the original work for its findings. Save a collection to share your selection of sources.

KEEP EXPLORING

Related citations

The production of (R)-2-hydroxy-1-phenyl-propan-1-one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor.

Benzaldehyde lyase (BAL; E.C. 4.1.2.38) from Pseudomonas fluorescens Biovar I catalyzes the reversible formation of benzoins from aromatic aldehydes, and, moreover, the coupling of aromatic with aliphatic aldehydes yielding derivatives of (R)-2-hydroxy-1-phenyl- propan-1-one (R)-HPPs), which are important chiral building blocks. In this paper, we report on the development of a reactor system that allows the selective production of substituted (R)-HPP-derivatives. The reaction systems yielding (R)-1-(3-chloro-phenyl)-2-hydroxy- propan-1-one, (R)-2-hydroxy-3-methoxy-1-(4-methoxy-phenyl)-propan-1-one, and (R)-2-hydroxy-3,3-dimethoxy-1-phenyl-propan-1-one were investigated. A kinetic model optimized by batch experiments was developed, for the description of both batch and continuously operated reactors. This model was used to describe the HPP production in a continuously operated enzyme membrane reactor. The reactor type used combines the advantages of high conversion and excellent selectivity with high space-time yields and total turnover numbers of up to ttn=43,000. Products were obtained in high yield on a gram scale.

Acetone↗

Analysis of the inter-molecular interactions between amino acids and acetone by THz spectroscopy.

The THz spectra of amino acids after application of spots of acetone were measured. The 0.6 THz band was commonly observed in many amino acids that formed the intra-molecular salt structure. The band can be attributed to the interaction vibration from the common structural configuration of amino acids and acetone molecules. The evidence suggests that the vibration between the amino acids with intra-molecular salt structure and acetone has a peak at 0.6 THz. A model of the interaction vibration of acetone and the functional groups of amino acids is proposed.

Acetone↗

Two-directional elaboration of hydroxyacetone under thermodynamically controlled conditions: allylation or 2-propynylation and aldol reaction.

Enolate generated from O-(tetrahydropyran-2-yl)hydroxyacetone under thermodynamically controlled conditions (1.3 equiv of NaH, THF, 0 degrees C to rt) was allylated at the carbon bearing the protected hydroxy group with very high regioselectively. When tert-BuOH, equivalent to the excessive portion of initially added NaH, was introduced into the mixture followed by addition of aldehyde, aldol reaction took place on the methyl group to give 1-substituted 4-hydroxy-(1E),6-heptadien-3-one in acceptable yields after acidic treatment of the mixture for dehydration and deprotection. Introducing a chiral auxiliary protecting group into hydroxyacetone led to asymmetric allylation though stereoselectivity was around 50% ee. Thus, the hidden aspect of the chemoselective nature of protected hydroxyacetone-derived enolate generated under thermodynamically controlled conditions has opened a new avenue for two-directional elaboration of hydroxyacetone that should be potentially useful in organic synthesis.

Acetone↗