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Chemical Compound Review:

p,p'-Biphenol 4-(4-hydroxyphenyl)phenol

Synonyms: p,p'-Diphenol, PubChem8927, CHEMBL76398, SureCN15632, NSC-8711, ...

Yoshikawa, A. et al., Nakagawa, Y. et al., McGirr, L.G. et al., Subrahmanyam, V.V. et al., Ponnu, A. et al., et al.

Yoshikawa, Saito, Maruyama,

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Disease relevance of ASM DOD

Inhibition of melanogenic activity by 4,4'-dihydroxybiphenyl in melanoma cells [1].

High impact information on ASM DOD

However, both 2,2'- and 4,4'-biphenol caused significant cell cycle delay and mitotic inhibition [2].
The complexes of either dimethyl viologen (MV) or diheptyl viologen (HV) with 4,4'-biphenol (BP) (MVBP or HVBP complexes) have identical charge-transfer spectra and kinetics in ethylene glycol with approximately 900 fs ET decay [3].
Lignan compounds and 4,4'-dihydroxybiphenyl protect C2C12 cells against damage from oxidative stress [4].
A simple compound, 4,4'-dihydroxybiphenyl, which was found to be a common component of Gomisin J and GR-12, also largely prevented H(2)O(2)-induced cell death and almost completely prevented H(2)O(2)-induced increases in p38 MAPK phosphorylation [4].
A comparative study of the toxic effects of BPA and some bisphenols on cell viability (at 1.0 mM) and mitochondrial respiration (at 0.25 mM) revealed that 4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol (diethylstilbestrol) was more toxic than BPA, followed by 4,4'-methylenediphenol and 4,4'-biphenol [5].

Biological context of ASM DOD

Charge recombination (CR) kinetics following photoinduced charge transfer are measured by optical transient absorption for complexes of dimethyl viologen and diheptyl viologen with 4,4'-biphenol (MVBP and HVBP) in methanol [6].
However, enzymic hydrolysis of DNA releases the bound polymers. p,p'-Biphenol, however, did not bind to DNA following peroxidase-catalysed oxidation, but o,o'-biphenol readily binds to DNA following peroxidase-catalysed oxidation [7].

Anatomical context of ASM DOD

2. The majority of the metabolized 14C-phenol was bound to bone marrow proteins. o,o'-Biphenol and p,p'-biphenol were the principal non-protein-bound products [8].

Associations of ASM DOD with other chemical compounds

The same conjugate was formed in the bone marrow homogenate-hydrogen peroxide system. p,p'-Biphenoquinone reduction by glutathione to p,p'-biphenol without glutathione oxidation was explained by the rapid reduction of p,p'-biphenoquinone by 3-(glutathion-S-yl)-p,p'-biphenol [9].
Extraction of fresh sporophores of the fungus Agaricus xanthodermus yields 4,4'-dihydroxy-azobenzene, phenol, p-quinol, and 4,4'-dihydroxybiphenyl [10].

Gene context of ASM DOD

In our previous study, we showed that 4,4'-dihydroxybiphenyl (44'-BP) reduced melanin content via the inhibition of tyrosinase [1].

References

Inhibition of melanogenic activity by 4,4'-dihydroxybiphenyl in melanoma cells. No, J.K., Kim, Y.J., Lee, J.S., Chung, H.Y. Biol. Pharm. Bull. (2006) [Pubmed]
Sister chromatid exchange induction in human lymphocytes exposed to benzene and its metabolites in vitro. Erexson, G.L., Wilmer, J.L., Kligerman, A.D. Cancer Res. (1985) [Pubmed]
Ultrafast electron-transfer and solvent adiabaticity effects in viologen charge-transfer complexes. Ponnu, A., Sung, J., Spears, K.G. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory (2006) [Pubmed]
Lignan compounds and 4,4'-dihydroxybiphenyl protect C2C12 cells against damage from oxidative stress. Yoshikawa, A., Saito, Y., Maruyama, K. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
Metabolism and cytotoxicity of bisphenol A and other bisphenols in isolated rat hepatocytes. Nakagawa, Y., Tayama, S. Arch. Toxicol. (2000) [Pubmed]
Solvent adiabaticity effects on ultrafast electron transfer in viologen charge transfer complexes. Moran, A.M., Aravindan, P., Spears, K.G. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
Phenol oxidation product(s), formed by a peroxidase reaction, that bind to DNA. Subrahmanyam, V.V., O'Brien, P.J. Xenobiotica (1985) [Pubmed]
Peroxidase/hydrogen peroxide--or bone marrow homogenate/hydrogen peroxide--mediated activation of phenol and binding to protein. Subrahmanyam, V.V., McGirr, L.G., O'Brien, P.J. Xenobiotica (1990) [Pubmed]
Peroxidase-catalyzed-3-(glutathion-S-yl)-p,p'-biphenol formation. McGirr, L.G., Subrahmanyam, V.V., Moore, G.A., O'Brien, P.J. Chem. Biol. Interact. (1986) [Pubmed]
Constituents of Agaricus xanthodermus Genevier: the first naturally endogenous azo compound and toxic phenolic metabolites. Gill, M., Strauch, R.J. Z. Naturforsch., C, Biosci. (1984) [Pubmed]

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