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Chemical Compound Review:

ACMC-1CP9S undec-10-ynoic acid

Synonyms: AG-L-22767, ANW-26270, GEO-02443, FR-2153, STOCK1N-02358, ...

Ortiz de Montellano, P.R. et al., CaJacob, C.A. et al., Lawson, T.A., Cornu-Chagnon, M.C. et al., Lie Ken Jie, M.S. et al.

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High impact information on Hendecynoic acid

1) The observation of protein rather than heme alkylation in the reaction of cytochrome P4504A1 with 10-undecynoic acid supports the argument that the enzyme circumvents the inherent preference for omega-1 hydroxylation by restricting access to the ferryl oxygen [1].
The hepatic cytochrome P-450 isozymes that catalyze omega- and (omega - 1)-hydroxylation of lauric acid are specifically inactivated in vitro but not in vivo by 10-undecynoic acid [2].
10-Undecynoic acid gave the highest conversion rate of esterification with each kind of lipase used [3].
10-Undecynoic acid, a lauric acid hydroxylase inhibitor, inhibited the increase in BHP and HPOP mutagenicity by 80-90% but did not affect that of BOP [4].
Specific inhibition of LAH activity (-52%) by 10-undecynoic acid partially prevented induction of peroxisomal PCOA (-32%) [5].

References

Mechanism-based probes of the topology and function of fatty acid hydroxylases. Ortiz de Montellano, P.R., Chan, W.K., Tuck, S.F., Kaikaus, R.M., Bass, N.M., Peterson, J.A. FASEB J. (1992) [Pubmed]
Mechanism-based in vivo inactivation of lauric acid hydroxylases. CaJacob, C.A., Ortiz de Montellano, P.R. Biochemistry (1986) [Pubmed]
Studies of lipase-catalyzed esterification reactions of some acetylenic fatty acids. Lie Ken Jie, M.S., Xun, F. Lipids (1998) [Pubmed]
Involvement of lauric acid hydroxylase in the activation of beta-substituted nitrosamines. Lawson, T.A. Cancer Lett. (1991) [Pubmed]
Fenofibrate: metabolism and species differences for peroxisome proliferation in cultured hepatocytes. Cornu-Chagnon, M.C., Dupont, H., Edgar, A. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1995) [Pubmed]

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