ChemInform Abstract: Racemic and Enantiomeric all‐trans‐Fecapentaene‐12 and‐14.

Pfaendler, H. R.; Maier, Franz Karl; Klar, S.; Goeggelmann, W.

doi:10.1002/chin.198832327

Cited by 3 publications

(4 citation statements)

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“…Our experience suggests that such measurements be made routine during toxicological studies with fecapentaenes. We thus strongly support the recent quality control recommendations made by Pfaendler et al concerning biological work with these "extremely sensitive" compounds (39). The crucial importance of confirming the purity and concentration of fecapentaene preparations during each application to a biological system cannot be overstated.…”

Section: Discussionsupporting

confidence: 83%

Decomposition and quality control considerations in biological work with fecapentaene preparations

Pj²,

Anjo³

et al. 1989

Chem. Res. Toxicol.

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Solutions of synthetic fecapentaene 12 (FP-12) intended for carcinogenicity studies were found to decompose extremely rapidly during customary dosage procedures. Apparent half-lives as short as 15 min were observed. While rates and even the qualitative course of decomposition were surprisingly variable in replicate experiments, high concentration and exposure to air were confirmed to be especially important destabilizing influences. The results suggested a primary role for a radical decomposition mechanism in the presence of atmospheric oxygen. Consistent with this hypothesis, FP-12 solutions were significantly stabilized by the radical chain-breaking antioxidant vitamin E. On the other hand, dithiothreitol greatly destabilized FP-12, presumably because of its nucleophilicity. The diacetyl diester of FP-12 was more soluble than the parent diol, but its decomposition rates in the presence and absence of vitamin E were similar to those of unesterified FP-12. Ultraviolet irradiation of an all-trans-FP-12 solution decreased its concentration by 70% in 0.5 min. The mutagenicities of the decomposition/isomerization products of FP-12, as studied in Salmonella typhimurium tester strain TA 100, ranged from negligible to comparable with all-trans-FP-12 itself. It is concluded that unchecked decomposition of fecapentaene preparations can profoundly affect biological tests therewith. While this can be largely controlled through the use of rigorous precautions, including protection from air, light, nucleophiles, and acids as well as selection of the lowest concentration compatible with the application at hand, the data argue strongly for inclusion of appropriate quality control measures in all future dosing operations to prove that the biological activity reported is that of the fecapentaene itself rather than that of a decomposed dosing solution.

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Section: Discussionsupporting

confidence: 83%

Decomposition and quality control considerations in biological work with fecapentaene preparations

Pj²,

Anjo³

et al. 1989

Chem. Res. Toxicol.

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“…The fourth synthesis of fecapentaene 12 avoids the use of the Wittig or Horner-Wittig reaction and instead uses a modified Whiting reaction as the key step (Figure 5) (39,40). The propenal 11 was prepared by reaction of the racemic tosylate 10 with the tetrabutylammonium salt of malondialdehyde.…”

Section: Osibu'me2mentioning

confidence: 99%

“…Deprotection of 14 gave crystalline racemic fecapentaene 12 (1). The use of chiral precursors to 10 led to the synthesis of both natural (S)-(+)-fecapentaene 12 and its enantiomer, and the use of a homologue of alkyne 12 led to the synthesis of racemic and (S)-(+)-fecapentaene 14 (40).…”

Section: Osibu'me2mentioning

confidence: 99%

The fecapentaenes, potent mutagens from human feces

Rl²,

Td³

1990

Chem. Res. Toxicol.

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“…The ultimate origin of the fecapentaenes can be either the diet or cell membranes of the colonic bacterial flora and human colon itself (115). After elucidation of the general structure of the fecapentaenes, several methods were developed to synthesize FP-12 and FP-14 as well as various fecapentaene analogues (116)(117)(118)(119)(120)(121). The availability of these synthetic compounds initiated numerous studies on both /« v/rro and m v/vo genotoxic effects of fecapentaenes and their mode of action.…”

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confidence: 99%

Fecapentaenes and risk for colorectal cancer

Kok¹

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ChemInform Abstract: Racemic and Enantiomeric all‐trans‐Fecapentaene‐12 and‐14.

Abstract: ChemInform Abstract The racemic title compounds (V) or both enantiomers of (V) induce mutagenic effects in the Ames assay.

Cited by 3 publications

References 1 publication

Decomposition and quality control considerations in biological work with fecapentaene preparations

Decomposition and quality control considerations in biological work with fecapentaene preparations

The fecapentaenes, potent mutagens from human feces

Fecapentaenes and risk for colorectal cancer

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