Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Editor

Personal info

View

About

Terms

Javascript disabled

Please enable Javascript support in your browser to use this application.

Instructions on how to enable JavaScript on different browsers can be found here: http://www.google.com/support/bin/answer.py?answer=23852.

[edit this page]

Chemical Compound Review:

PubChem19828 2-ethynylnaphthalene

Synonyms: CCRIS 4255, AG-D-50204, CHEMBL1743361, ANW-46619, AC1L3GDQ, ...

Foroozesh, M. et al., Yun, C.H. et al., Roberts, E.S. et al., Tai, H.L. et al., Roberts, E.S. et al., et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

High impact information on CCRIS 4255

2-Ethynylnaphthalene (2EN) had previously been demonstrated to be a mechanism-based inactivator of rat cytochrome P450 (P450) 1A2 [Hammons, G.J., Alworth, W.L., Hopkins, N.E., Guengerich, F. P., & Kadlubar, F. F. (1989) Chem. Res. Toxicol. 2, 367-374] [1].
The structural basis for 2EN and 1APE susceptibility was assessed using active site mutants [2].
Neither 4PBi nor 2EN affected diagnostic activities of human microsomal P450 2E1, 2C9/10, 3A4, or 2C19 [3].
Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: identification of an active-site peptide [4].
The rate constants for inactivation by the arylalkynes in descending order of effectiveness for the top five compounds were 9EPh>9PPh>1EN, 2EN, 2PN for 2B1, 9EPh>2EN>4EP>1EN, 1EA for 2B4, and 9EPh>1EA>4EP, 9PPh>2EN for 2B11 [5].

Anatomical context of CCRIS 4255

In agreement with previous reports [Yun, C.-H., Hammons, G. J., Jones, G., Martin, M. V., Hopkins, N. E., Alworth, W. L., and Guengerich, F. P. (1992) Biochemistry 31, 10556-10563], 2-ethynylnaphthalene (2EN) was not a suicide inhibitor of the P450 1A2 activity in human liver microsomes but did inactivate purified human P450 1A2 [3].

Gene context of CCRIS 4255

Conversely, 2-ethynylnaphthalene, a suicide inhibitor of CYP1A2 and antibody to rat CYP1A2, had no inhibitory effect on the hepatic microsomal metabolism of TCDF [6].

References

Modification of cytochrome P450 1A2 enzymes by the mechanism-based inactivator 2-ethynylnaphthalene and the photoaffinity label 4-azidobiphenyl. Yun, C.H., Hammons, G.J., Jones, G., Martin, M.V., Hopkins, N.E., Alworth, W.L., Guengerich, F.P. Biochemistry (1992) [Pubmed]
Identification of selective mechanism-based inactivators of cytochromes P-450 2B4 and 2B5, and determination of the molecular basis for differential susceptibility. Strobel, S.M., Szklarz, G.D., He, Y., Foroozesh, M., Alworth, W.L., Roberts, E.S., Hollenberg, P.F., Halpert, J.R. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Foroozesh, M., Primrose, G., Guo, Z., Bell, L.C., Alworth, W.L., Guengerich, F.P. Chem. Res. Toxicol. (1997) [Pubmed]
Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: identification of an active-site peptide. Roberts, E.S., Hopkins, N.E., Alworth, W.L., Hollenberg, P.F. Chem. Res. Toxicol. (1993) [Pubmed]
Inactivation of cytochrome P450s 2B1, 2B4, 2B6, and 2B11 by arylalkynes. Roberts, E.S., Hopkins, N.E., Foroozesh, M., Alworth, W.L., Halpert, J.R., Hollenberg, P.F. Drug Metab. Dispos. (1997) [Pubmed]
Cytochrome P4501A1 mediates the metabolism of 2,3,7,8-tetrachlorodibenzofuran in the rat and human. Tai, H.L., McReynolds, J.H., Goldstein, J.A., Eugster, H.P., Sengstag, C., Alworth, W.L., Olson, J.R. Toxicol. Appl. Pharmacol. (1993) [Pubmed]

Contributions to this collaborative article are from individual authors of WikiGenes or mined by the WikiGenes Data Mining Engine from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.About WikiGenes Open Access Licence Privacy Policy Terms of Use apsburg

The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.