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Chemical Compound Review

Panoxyl     phenylcarbonyl benzenecarboperoxoate

Synonyms: Acetoxyl, Asidopan, Benzagel, Brevoxyl, Desanden, ...
 
 
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Disease relevance of BENZOYL PEROXIDE

 

High impact information on BENZOYL PEROXIDE

  • In comparison, the effects of anthralin, phorbol-12,13-didecanoate, benzoyl peroxide, H2O2, and phorbol-12,13-dibenzoate were much smaller, whereas the nontumor promoter phorbol, the hyperplastic agent ethyl phenylpropiolate, and the stage 1 promoter 4-O-methyl TPA did not alter GSH peroxidase and ODC activities [4].
  • The non-phorbol ester tumor promoter benzoyl peroxide also elevated XO activity consistent with the degree of induced hyperplasia [5].
  • Benzoyl peroxide (BP) (10(-4) M) induced SSB in basal keratinocytes within 1 h, and attached cells showed extensive SSB by 12 h [6].
  • Retinoic acid had only a slight effect on BP-induced SSB, and 1 of 3 TPA-resistant cell lines developed SSB when exposed to BP [6].
  • These results suggest that TPA-induced SSB in epidermal cells are an indirect consequence of the induction of terminal differentiation, whereas BP produces SSB by a more direct mechanism of DNA damage [6].
 

Chemical compound and disease context of BENZOYL PEROXIDE

 

Biological context of BENZOYL PEROXIDE

 

Anatomical context of BENZOYL PEROXIDE

 

Associations of BENZOYL PEROXIDE with other chemical compounds

  • Following initiation, groups of female SENCAR mice received the following promoter doses: TPA (1.0 or 2.0 micrograms per mouse); MEZ (2.0 micrograms per mouse); BzPo (20.0 mg per mouse); and CHRY (52.8 micrograms per mouse) [21].
  • Copper ion-mediated modification of bases in DNA in vitro by benzoyl peroxide [22].
  • Inhibitory effect of a flavonoid antioxidant silymarin on benzoyl peroxide-induced tumor promotion, oxidative stress and inflammatory responses in SENCAR mouse skin [23].
  • The effects of five non-mutagenic carcinogens--Aroclor 1260, benzoyl peroxide (BP), phenobarbital (PB), 12-O-tetradecanoyl-phorbol-13-acetate (TPA) and 1,1'-(2,2,2-trichloroethylidene)bis[4-chlorobenzene] (DDT)--on gap junctional intercellular communication (GJIC) were tested in a cell line consisting of initiated cells (3PC) [24].
  • Beginning at the 20th week (DMBA/TPA group) and at the 27th week (UVB group), malignant conversion was achieved by twice weekly topical application of TPA or free radical-generating compounds benzoyl peroxide (BPO), 2,2-azobis(2-amidinopropane) (ABP) and tert-butyl peroxybenzoate (BPB) [25].
 

Gene context of BENZOYL PEROXIDE

  • Keratin 10, identified by use of specific antibodies and by microsequencing, was demonstrated in vitro to be oxidizable by ultraviolet A irradiation, hypochlorite, and benzoyl peroxide [26].
  • Of the other promoters examined, anthralin (5 microM), benzoyl peroxide (10 microM), and okadaic acid (1 microM) induced PGHS-2 mRNA with different kinetics and to different extents [27].
  • To determine if proliferin genes respond to tumor promoters in vivo, RNA was extracted from the whole skin of SENCAR mice after single applications of 2 or 20 microg 12-O-tetradecanoylphorbol-13-acetate (TPA); 3.2 or 32 nmole), 20 or 40 mg benzoyl peroxide (BPO; 83, 165 micromole), or acetone vehicle alone (2.72 mmole) [28].
  • We have found that E-73, an acetoxyl analogue of cycloheximide, specifically blocks TNF-induced ICAM-1 expression even at concentrations unable to affect protein synthesis [29].
  • BzPo elevated the levels of Cx26 and Cx43 transcripts later (peak at 2-4 d) [30].
 

Analytical, diagnostic and therapeutic context of BENZOYL PEROXIDE

  • The ability of benzoyl peroxide to enhance the progression of benign tumors to cancer should be considered when determining the human risk from exposure to this widely used chemical agent; in addition, biological assays specifically testing malignant progression may be essential and beneficial for determining an agent's carcinogenic risk [2].
  • The ability of benzoyl peroxide to inhibit metabolic co-operation in rodent cell cultures may be relevant to its recently reported tumour promoting activity in mouse epidermis [31].
  • Northern blot analysis indicated that topical application of TPA, anthralin, mezerein, or benzoyl peroxide to SENCAR mice resulted in an increased expression of epidermal IL-1 alpha mRNA [7].
  • Reverse transcriptase (RT)-polymerase chain reactions (PCR) detected fully-processed MRP/plf-mRNA 16-48 h after TPA treatments in five of six animals, and in three of six BPO-treated animals [28].
  • The specificity of the stability-indicating HPLC and iodometric procedures are presented for benzoyl peroxide [32].

References

  1. Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound. Slaga, T.J., Klein-Szanto, A.J., Triplett, L.L., Yotti, L.P., Trosko, K.E. Science (1981) [Pubmed]
  2. Enhanced malignant progression of mouse skin tumors by the free-radical generator benzoyl peroxide. O'Connell, J.F., Klein-Szanto, A.J., DiGiovanni, D.M., Fries, J.W., Slaga, T.J. Cancer Res. (1986) [Pubmed]
  3. Topical alpha-tocotrienol supplementation inhibits lipid peroxidation but fails to mitigate increased transepidermal water loss after benzoyl peroxide treatment of human skin. Weber, S.U., Thiele, J.J., Han, N., Luu, C., Valacchi, G., Weber, S., Packer, L. Free Radic. Biol. Med. (2003) [Pubmed]
  4. Effects of combined treatments with selenium, glutathione, and vitamin E on glutathione peroxidase activity, ornithine decarboxylase induction, and complete and multistage carcinogenesis in mouse skin. Perchellet, J.P., Abney, N.L., Thomas, R.M., Guislain, Y.L., Perchellet, E.M. Cancer Res. (1987) [Pubmed]
  5. Murine epidermal xanthine oxidase activity: correlation with degree of hyperplasia induced by tumor promoters. Pence, B.C., Reiners, J.J. Cancer Res. (1987) [Pubmed]
  6. Association of DNA strand breaks with accelerated terminal differentiation in mouse epidermal cells exposed to tumor promoters. Hartley, J.A., Gibson, N.W., Zwelling, L.A., Yuspa, S.H. Cancer Res. (1985) [Pubmed]
  7. Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin tumor-promoter-caused induction of epidermal interleukin-1 alpha mRNA and protein expression in SENCAR mice by green tea polyphenols. Katiyar, S.K., Rupp, C.O., Korman, N.J., Agarwal, R., Mukhtar, H. J. Invest. Dermatol. (1995) [Pubmed]
  8. A randomized, double-blind comparison of a clindamycin phosphate/benzoyl peroxide gel formulation and a matching clindamycin gel with respect to microbiologic activity and clinical efficacy in the topical treatment of acne vulgaris. Cunliffe, W.J., Holland, K.T., Bojar, R., Levy, S.F. Clinical therapeutics. (2002) [Pubmed]
  9. The comparative efficacy of benzoyl peroxide 5%/erythromycin 3% gel and erythromycin 4%/zinc 1.2% solution in the treatment of acne vulgaris. Chu, A., Huber, F.J., Plott, R.T. Br. J. Dermatol. (1997) [Pubmed]
  10. Acne vulgaris: recent advances in pathogenesis and treatment. Caro, I. The Journal of family practice. (1977) [Pubmed]
  11. Alpha-tocopherol amplifies benzoyl peroxide free radical decomposition in a chemical system. Rota, C., Tomasi, A., Iannone, A. Free Radic. Res. (2006) [Pubmed]
  12. Differential oxidative stress induced by two different types of skin tumor promoters, benzoyl peroxide and 12-O-tetradecanoylphorbol-13-acetate. Durán, H.A., de Rey, B.M. Carcinogenesis (1991) [Pubmed]
  13. Copper-dependent site-specific mutagenesis by benzoyl peroxide in the supF gene of the mutation reporter plasmid pS189. Akman, S.A., Doroshow, J.H., Kensler, T.W. Carcinogenesis (1992) [Pubmed]
  14. Elevated expression and point mutation of the Ha-ras proto-oncogene in mouse skin tumors promoted by benzoyl peroxide and other promoting agents. Pelling, J.C., Fischer, S.M., Neades, R., Strawhecker, J., Schweickert, L. Carcinogenesis (1987) [Pubmed]
  15. The effect of dietary lipid on skin tumor promotion by benzoyl peroxide: comparison of fish, coconut and corn oil. Locniskar, M., Belury, M.A., Cumberland, A.G., Patrick, K.E., Fischer, S.M. Carcinogenesis (1991) [Pubmed]
  16. Benzoyl peroxide activation of protein kinase C activity in epidermal cell membranes. Donnelly, T.E., Pelling, J.C., Anderson, C.L., Dalbey, D. Carcinogenesis (1987) [Pubmed]
  17. Benzoyl peroxide promotes the formation of melanotic tumors in the skin of 7,12-dimethylbenz[a]anthracene-initiated Syrian golden hamsters. Schweizer, J., Loehrke, H., Edler, L., Goerttler, K. Carcinogenesis (1987) [Pubmed]
  18. Inhibition of gap junctional intercellular communication and delocalization of the cell adhesion molecule E-cadherin by tumor promoters. Jansen, L.A., Mesnil, M., Jongen, W.M. Carcinogenesis (1996) [Pubmed]
  19. Topical benzoyl peroxide increases the sebum excretion rate. Pierard-Franchimont, C., Melotte, P., Pierard, G.E. Br. J. Dermatol. (1984) [Pubmed]
  20. Plant polyphenols inhibit benzoyl peroxide-induced superoxide anion radical production and diacylglyceride formation in murine peritoneal macrophages. Kaul, A., Khanduja, K.L. Nutrition and cancer. (1999) [Pubmed]
  21. Further studies on the influence of initiation dose on papilloma growth and progression during two-stage carcinogenesis in SENCAR mice. DiGiovanni, J., Walker, S.E., Aldaz, C.M., Slaga, T.J., Conti, C.J. Carcinogenesis (1993) [Pubmed]
  22. Copper ion-mediated modification of bases in DNA in vitro by benzoyl peroxide. Akman, S.A., Kensler, T.W., Doroshow, J.H., Dizdaroglu, M. Carcinogenesis (1993) [Pubmed]
  23. Inhibitory effect of a flavonoid antioxidant silymarin on benzoyl peroxide-induced tumor promotion, oxidative stress and inflammatory responses in SENCAR mouse skin. Zhao, J., Lahiri-Chatterjee, M., Sharma, Y., Agarwal, R. Carcinogenesis (2000) [Pubmed]
  24. The use of initiated cells as a test system for the detection of inhibitors of gap junctional intercellular communication. Jansen, L.A., Jongen, W.M. Carcinogenesis (1996) [Pubmed]
  25. All-trans retinoic acid protects against conversion of chemically induced and ultraviolet B radiation-induced skin papillomas to carcinomas. Athar, M., Agarwal, R., Wang, Z.Y., Lloyd, J.R., Bickers, D.R., Mukhtar, H. Carcinogenesis (1991) [Pubmed]
  26. Protein oxidation in human stratum corneum: susceptibility of keratins to oxidation in vitro and presence of a keratin oxidation gradient in vivo. Thiele, J.J., Hsieh, S.N., Briviba, K., Sies, H. J. Invest. Dermatol. (1999) [Pubmed]
  27. Multifactor regulation of prostaglandin H synthase-2 in murine keratinocytes. Maldve, R.E., Fischer, S.M. Mol. Carcinog. (1996) [Pubmed]
  28. Mitogen-regulated protein/proliferin mRNA induction following single applications of tumor promoters to murine skin. Parfett, C.L. Mol. Carcinog. (2005) [Pubmed]
  29. E-73, an acetoxyl analogue of cycloheximide, blocks the tumor necrosis factor-induced NF-kappaB signaling pathway. Sugimoto, H., Kataoka, T., Igarashi, M., Hamada, M., Takeuchi, T., Nagai, K. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  30. Effect of diverse tumor promoters on the expression of gap-junctional proteins connexin (Cx)26, Cx31.1, and Cx43 in SENCAR mouse epidermis. Budunova, I.V., Carbajal, S., Slaga, T.J. Mol. Carcinog. (1996) [Pubmed]
  31. Benzoyl peroxide interferes with metabolic co-operation between cultured human epidermal keratinocytes. Lawrence, N.J., Parkinson, E.K., Emmerson, A. Carcinogenesis (1984) [Pubmed]
  32. Quantitative determination of benzoyl peroxide by high-performance liquid chromatography and comparison to the iodometric method. Gaddipati, N., Volpe, F., Anthony, G. Journal of pharmaceutical sciences. (1983) [Pubmed]
 
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