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Chemical Compound Review

MCPBA     3-chlorobenzenecarboperoxoic acid

Synonyms: m-CPBA, PubChem10937, CCRIS 639, ARONIS23877, CHEMBL458855, ...
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High impact information on NSC97094


Biological context of NSC97094


Anatomical context of NSC97094

  • The effects of oxygen active species (.OH and O(2)(.-) radicals) photogenerated by the novel photosensitizer m-chloroperbenzoic acid (m-CPBA) on human erythrocyte integrity and stability were studied [11].

Associations of NSC97094 with other chemical compounds


Gene context of NSC97094

  • The reaction with hydrogen peroxide converted the heme of the heme oxygenase-2 fragment complex into a verdoheme-like intermediate, while the reaction with m-chloroperbenzoic acid yielded a oxoferryl species [16].
  • Whereas the O-O bond of hydroperoxides containing an electron-donating tert-alkyl group is cleaved homolytically, an electron-withdrawing substituent such as an acyl group in m-chloroperoxybenzoic acid (m-CPBA) facilitates O-O bond heterolysis [17].
  • At pH 7 and 15 degrees C, the rate constant of the reaction between 3-chloroperoxybenzoic acid and ferric MPO was similar to that with hydrogen peroxide (1.8x10(7) M(-1) s(-1) and 1.4x10(7) M(-1) s(-1), respectively) [18].
  • Treatment of Delta 4-3-ketosteroids with m-chloroperbenzoic acid at 0 degrees C produced the corresponding steroidal seven-membered A-ring epoxy lactones [19].
  • m-Chloroperoxybenzoic acid (CPBA) was tested for its ability to induce the ornithine decarboxylase (ODC) marker of skin tumor promotion [15].

Analytical, diagnostic and therapeutic context of NSC97094


  1. Catalase reaction by myoglobin mutants and native catalase: mechanistic investigation by kinetic isotope effect. Kato, S., Ueno, T., Fukuzumi, S., Watanabe, Y. J. Biol. Chem. (2004) [Pubmed]
  2. Involvement of phospholipid hydroperoxide glutathione peroxidase in the modulation of prostaglandin D2 synthesis. Sakamoto, H., Imai, H., Nakagawa, Y. J. Biol. Chem. (2000) [Pubmed]
  3. Effect of distal cavity mutations on the formation of compound I in catalase-peroxidases. Regelsberger, G., Jakopitsch, C., Rüker, F., Krois, D., Peschek, G.A., Obinger, C. J. Biol. Chem. (2000) [Pubmed]
  4. On the formation and reactivity of compound I of the His-64 myoglobin mutants. Matsui, T., Ozaki, S., Watanabe, Y. J. Biol. Chem. (1997) [Pubmed]
  5. Reactions of prostaglandin endoperoxide synthase and its compound I with hydroperoxides. Bakovic, M., Dunford, H.B. J. Biol. Chem. (1996) [Pubmed]
  6. Hepatic microsomal dealkylations. Inhibition by a tyrosine-copper (II) complex provided with superoxide dismutase activity. Richter, C., Azzi, A., Weser, U., Wendel, A. J. Biol. Chem. (1977) [Pubmed]
  7. Antitumor agents. 11. Synthesis and cytotoxic activity of epoxides of helenalin related derivatives. Lee, K.H., Kim, S.H., Furukawa, H., Piantadosi, C. J. Med. Chem. (1975) [Pubmed]
  8. Baeyer-Villiger oxidation promoted by reaction of peracids with cyclic oxocarbenium ions generated in situ from internal hemiketals. Hunt, K.W., Grieco, P.A. Org. Lett. (2000) [Pubmed]
  9. Ni(II)(TPA) as an efficient catalyst for alkane hydroxylation with m-CPBA. Nagataki, T., Tachi, Y., Itoh, S. Chem. Commun. (Camb.) (2006) [Pubmed]
  10. A rapid-scan spectrometric and stopped-flow study of compound I and compound II of Pseudomonas cytochrome c peroxidase. Rönnberg, M., Lambeir, A.M., Ellfolk, N., Dunford, H.B. Arch. Biochem. Biophys. (1985) [Pubmed]
  11. Photosensitization induced reactive oxygen species and oxidative damage in human erythrocytes. El-Missiry, M.A., Abou-Seif, M. Cancer Lett. (2000) [Pubmed]
  12. Synthesis of the marine epoxy sterol 9 alpha,11 alpha-epoxy-5 alpha-cholest-7-ene-3 beta,5,6 beta-triol. Migliuolo, A., Notaro, G., Piccialli, V., Sica, D. Steroids (1991) [Pubmed]
  13. Solid phase synthesis of pp60src-related phosphopeptides via 'global' phosphorylation and their use as substrates for enzymatic phosphorylation by casein kinase-2. Perich, J.W., Meggio, F., Pinna, L.A. Bioorg. Med. Chem. (1996) [Pubmed]
  14. Preparation and kinetic studies of immobilised yeast cytochrome c peroxidase. Cooper, J.M., McNeil, C.J., Bannister, J.V. Biotechnol. Appl. Biochem. (1991) [Pubmed]
  15. Ability of m-chloroperoxybenzoic acid to induce the ornithine decarboxylase marker of skin tumor promotion and inhibition of this response by gallotannins, oligomeric proanthocyanidins, and their monomeric units in mouse epidermis in vivo. Chen, G., Perchellet, E.M., Gao, X.M., Newell, S.W., Hemingway, R.W., Bottari, V., Perchellet, J.P. Anticancer Res. (1995) [Pubmed]
  16. Heme oxygenase-2. Properties of the heme complex of the purified tryptic fragment of recombinant human heme oxygenase-2. Ishikawa, K., Takeuchi, N., Takahashi, S., Matera, K.M., Sato, M., Shibahara, S., Rousseau, D.L., Ikeda-Saito, M., Yoshida, T. J. Biol. Chem. (1995) [Pubmed]
  17. Isolation of an oxomanganese(V) porphyrin intermediate in the reaction of a manganese(III) porphyrin complex and H2O2 in aqueous solution. Nam, W., Kim, I., Lim, M.H., Choi, H.J., Lee, J.S., Jang, H.G. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  18. Two-electron reduction and one-electron oxidation of organic hydroperoxides by human myeloperoxidase. Furtmüller, P.G., Burner, U., Jantschko, W., Regelsberger, G., Obinger, C. FEBS Lett. (2000) [Pubmed]
  19. Steroidal seven-membered A-ring epoxy lactones by oxidation of the corresponding Delta 4-3-ketosteroids. Gioia, M.L., Leggio, A., Pera, A.L., Perri, F., Pitrelli, A.F., Liguori, A. Steroids (2006) [Pubmed]
  20. Oxidation of 2-thioflavins by peroxides. Formation of flavin 2-S-oxides. Biemann, M., Claiborne, A., Ghisla, S., Massey, V., Hemmerich, P. J. Biol. Chem. (1983) [Pubmed]
  21. Determination of clethodim and its oxidation metabolites in crops by liquid chromatography with confirmation by LC/MS. Ishimitsu, S., Kaihara, A., Yoshii, K., Tsumura, Y., Nakamura, Y., Tonogai, Y. Journal of AOAC International. (2001) [Pubmed]
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