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Chemical Compound Review

Rhodiastab 83     1,3-diphenylpropane-1,3-dione

Synonyms: Karenzu DK2, SureCN39582, CHEMBL371523, NSC-6266, CCRIS 8445, ...
 
 
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Disease relevance of Dibenzoyl-methane

 

High impact information on Dibenzoyl-methane

  • Dibenzoylmethane modulates aryl hydrocarbon receptor function and expression of cytochromes P50 1A1, 1A2, and 1B1 [5].
  • We previously reported on the ability of dibenzoylmethane (DBM) and a relative, Parsol 1789, used as a ultraviolet A (UVA)-absorbing sunscreen, to generate free radicals upon illumination, and as a consequence, to inflict strand breaks in plasmid DNA in vitro [6].
  • Organic nanotubes of various diameters were fabricated from the isomeric molecule dibenzoylmethane (DBM) by using an immersing technique with ordered porous alumina membrane as the template [7].
  • Dibenzoylmethane, a natural dietary compound, induces HIF-1 alpha and increases expression of VEGF [8].
  • In this study, we investigated the effects of dibenzoylmethane (DBM), a natural dietary compound and an iron chelator, on HIF-1 pathway [8].
 

Chemical compound and disease context of Dibenzoyl-methane

 

Biological context of Dibenzoyl-methane

  • This paper explores the use of proteomics as a tool for identifying protein species whose expression has been altered by dibenzoylmethane (DBM) in LNCaP cells [10].
  • Results of the present investigations clearly indicate that dibenzoylmethane is a very potent antimutagenic agent, that could effectively inhibit mutagenicity induced by all the tested cooked food mutagens in both the frame shift (TA98) as well as the base pair mutation sensitive (TA100) strains of S. typhimurium [11].
  • Molecular structure and vibrational frequencies of 1,3-diphenyl-1,3-propanedione, known as dibenzoylmethane (DBM), have been investigated by means of density functional theory (DFT) calculations [12].
 

Anatomical context of Dibenzoyl-methane

 

Associations of Dibenzoyl-methane with other chemical compounds

 

Gene context of Dibenzoyl-methane

  • Dibenzoylmethane treatment at the same concentrations did not induce GSTP1-1 expression and significantly stimulated QR expression only at the 2.0 microM concentration [9].
  • The protection factors were compared with that found for the references: Nivea sun Spray LSF 5, octylmethoxycinnamate (OMC) and 4-tert.-butyl-4'-methoxy dibenzoylmethane (BM-DBM) [17].
 

Analytical, diagnostic and therapeutic context of Dibenzoyl-methane

  • Dibenzoylmethane (DBM), a minor beta-diketone constituent of licorice and sunscreens, has been shown to exhibit anti-neoplastic effects in chemically induced skin and mammary cancers in several animal models [4].

References

  1. Inhibition by diacylmethane derivatives of mutagenicity and nucleic acid binding of 2-aminofluorene derivatives. Wang, C.Y., Lee, M.S., Nagase, H., Zukowski, K. J. Natl. Cancer Inst. (1989) [Pubmed]
  2. Effect of the beta-diketones diferuloylmethane (curcumin) and dibenzoylmethane on rat mammary DNA adducts and tumors induced by 7,12-dimethylbenz[a]anthracene. Singletary, K., MacDonald, C., Iovinelli, M., Fisher, C., Wallig, M. Carcinogenesis (1998) [Pubmed]
  3. Effect of dietary curcumin and dibenzoylmethane on formation of 7,12-dimethylbenz[a]anthracene-induced mammary tumors and lymphomas/leukemias in Sencar mice. Huang, M.T., Lou, Y.R., Xie, J.G., Ma, W., Lu, Y.P., Yen, P., Zhu, B.T., Newmark, H., Ho, C.T. Carcinogenesis (1998) [Pubmed]
  4. Dibenzoylmethane induces cell cycle deregulation in human prostate cancer cells. Jackson, K.M., DeLeon, M., Verret, C.R., Harris, W.B. Cancer Lett. (2002) [Pubmed]
  5. Dibenzoylmethane modulates aryl hydrocarbon receptor function and expression of cytochromes P50 1A1, 1A2, and 1B1. MacDonald, C.J., Ciolino, H.P., Yeh, G.C. Cancer Res. (2001) [Pubmed]
  6. Increased oxidative modification of albumin when illuminated in vitro in the presence of a common sunscreen ingredient: protection by nitroxide radicals. Damiani, E., Carloni, P., Biondi, C., Greci, L. Free Radic. Biol. Med. (2000) [Pubmed]
  7. Nanotubes from isomeric dibenzoylmethane molecules. Zhao, L., Yang, W., Luo, Y., Zhai, T., Zhang, G., Yao, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  8. Dibenzoylmethane, a natural dietary compound, induces HIF-1 alpha and increases expression of VEGF. Mabjeesh, N.J., Willard, M.T., Harris, W.B., Sun, H.Y., Wang, R., Zhong, H., Umbreit, J.N., Simons, J.W. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  9. Inhibition of benzo[a]pyrene- and 1,6-dinitropyrene-DNA adduct formation in human mammary epithelial cells bydibenzoylmethane and sulforaphane. Singletary, K., MacDonald, C. Cancer Lett. (2000) [Pubmed]
  10. Proteomic analysis of proteins altered by dibenzoylmethane in human prostatic cancer LNCaP cells. Frazier, M.C., Jackson, K.M., Jankowska-Stephens, E., Anderson, M.G., Harris, W.B. Proteomics (2004) [Pubmed]
  11. Inhibitory effect of dibenzoylmethane on mutagenicity of food-derived heterocyclic amine mutagens. Shishu, n.u.l.l., Singla, A.K., Kaur, I.P. Phytomedicine (2003) [Pubmed]
  12. Vibrational assignment and structure of dibenzoylmethane A density functional theoretical study. Tayyari, S.F., Rahemi, H., Nekoei, A.R., Zahedi-Tabrizi, M., Wang, Y.A. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy (2007) [Pubmed]
  13. Inhibition by dietary dibenzoylmethane of mammary gland proliferation, formation of DMBA-DNA adducts in mammary glands, and mammary tumorigenesis in Sencar mice. Lin, C.C., Lu, Y.P., Lou, Y.R., Ho, C.T., Newmark, H.H., MacDonald, C., Singletary, K.W., Huang, M.T. Cancer Lett. (2001) [Pubmed]
  14. A novel sunscreen agent having antimelanoma activity. Nogueira, M.A., Magalhães, E.G., Magalhães, A.F., Biloti, D.N., Laverde, A., Pessine, F.B., Carvalho, J.E., Kohn, L.K., Antônio, M.A., Marsaioli, A.J. Farmaco (2003) [Pubmed]
  15. Analysis of serum iron by gel permeation high-performance liquid chromatography. Yuki, H., Hirano, N., Kawasaki, H., Yajima, T. J. Chromatogr. (1980) [Pubmed]
  16. Enzyme-mediated free radical polymerization of styrene. Singh, A., Ma, D., Kaplan, D.L. Biomacromolecules (2000) [Pubmed]
  17. Protection against UVB irradiation by natural filters extracted from lichens. Rancan, F., Rosan, S., Boehm, K., Fernández, E., Hidalgo, M.E., Quihot, W., Rubio, C., Boehm, F., Piazena, H., Oltmanns, U. J. Photochem. Photobiol. B, Biol. (2002) [Pubmed]
 
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