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Chemical Compound Review

PubChem19828     2-ethynylnaphthalene

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


  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
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