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Chemical Compound Review

BENZOPHENONE     diphenylmethanone

Synonyms: Benzoylbenzene, Diphenylketone, UPCMLD-DP071, PubChem20909, CCRIS 629, ...
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Disease relevance of benzophenone

  • Phenotypic changes induced by a novel benzophenone derivative and resultant suppression of cell proliferation in the human thymic acute lymphoblastic leukemia cell line HPB-ALL [1].
  • Data from erythema grading studies indicated that a significant degree of photoprotection was achieved with 6%, 3%, and 1% solutions of benzophenone compared with the control vehicle; the 6% solution was significantly more photoprotective than the 3% and 1% solutions [2].
  • Benzophenone derivatives: a novel series of potent and selective inhibitors of human immunodeficiency virus type 1 reverse transcriptase [3].
  • A series of benzophenone derivatives has been synthesized and evaluated as inhibitors of HIV-1 reverse transcriptase (RT) and the growth of HIV-1 in MT-4 cells [3].
  • Benzophenone-mediated photosensitization of 5'-amino-2',5'-dideoxyguanosine in aerated aqueous solution results in the formation of a predominant cyclic nucleoside together with an unstable nucleoside precursor [4].

High impact information on benzophenone


Chemical compound and disease context of benzophenone


Biological context of benzophenone

  • To illustrate the utility of this labeling, we tagged the NF-kappaB p50 transcription factor with benzophenone, cross-linked with UV light, and observed increased levels of p50 homodimerization in the presence of DNA and the binding protein myotrophin [14].
  • Involvement of singlet dioxygen formed by triplet-triplet energy transfer from benzophenone in the model reaction with DPAA/cytochrome c in the presence of DCP liposomes was suggested by quenching of the accompanying chemiluminescence upon addition of histidine and lycopene [15].
  • The cytotoxic effect by menadione-induced oxidative stress was monitored by the lucigenin- or luminol-amplified chemiluminescence, methylthiotetrazole (MTT) assay, and the antioxidative effects of various benzophenone compounds were evaluated [16].
  • Structure-activity relationship information revealed that introduction of an amino group at the ortho position of the benzophenone ring plays an integral role for increased growth inhibition [17].
  • Benzophenone derivatives were produced by acid hydrolysis of urine samples containing benzodiazepines and (or) their metabolites [18].

Anatomical context of benzophenone


Associations of benzophenone with other chemical compounds


Gene context of benzophenone

  • A fluorophosphonate inhibitor of FAAH containing a photoactivatable benzophenone group was synthesized and used to locate a region of the enzyme implicated in substrate binding [28].
  • In this report, we describe the photocross-linking of a BP-containing PTH antagonist, [Nle8,18,D-2-Nal12,Lys13(epsilon-BP),2-Nal23,Tyr34]bPT H(7-34)NH2 (ANT) to the recombinant hPTH/PTHrP receptor stably expressed in human embryonic kidney cells (HEK-293, clone C-21) [29].
  • The photo-induced cross-linking of the radioiodinated antagonist (125I-ANT) to the recombinant hPTH/PTHrP receptor followed by SDS-PAGE analysis reveals a single radiolabeled band of approximately 85kDa, similar to that observed after cross-linking of a radioiodinated BP-containing agonist [29].
  • Replacement of the key functional residues Phe4 and Trp9 with either benzophenone or (trifluoromethyl)aryldiazirine rendered this peptide antagonist photoactivatable, and as a consequence, it incorporated covalently upon photolysis into either uPAR domain I or domain III depending on the actual position of the photophore in the sequence [30].
  • Structure based design of benzophenone-based non-thiol farnesyltransferase inhibitors [31].

Analytical, diagnostic and therapeutic context of benzophenone

  • A method of obtaining such surfaces through UV-activated immobilization of binding proteins using a benzophenone derivative is reported [32].
  • The uniquely combined features of these benzophenone photoprobes promise robust and flexible methods for characterization of protein-protein interaction, either by mass spectrometry when a nonradioactive label is available or by autoradiography when using radioiodinated derivatives [33].
  • High-performance liquid chromatography of benzophenone derivatives for the determination of benzodiazepines in clinical emergencies [34].
  • The benzophenone formed is determined by means of electron-capture gas chromatography [35].
  • Further studies on ultraviolet-absorbing hydrogels for intraocular lenses: relationship between concentration of a polymerizable benzophenone, absorption, and extractability [36].


  1. Phenotypic changes induced by a novel benzophenone derivative and resultant suppression of cell proliferation in the human thymic acute lymphoblastic leukemia cell line HPB-ALL. Nakao, Y., Matsuda, S., Matsui, T., Nakagawa, T., Koizumi, T., Saida, T., Fujita, T. Cancer Res. (1984) [Pubmed]
  2. An animal model for evaluation of topical photoprotection against ultraviolet A (320-380 nm) radiation. Chew, S., DeLeo, V.A., Harber, L.C. J. Invest. Dermatol. (1987) [Pubmed]
  3. Benzophenone derivatives: a novel series of potent and selective inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Wyatt, P.G., Bethell, R.C., Cammack, N., Charon, D., Dodic, N., Dumaitre, B., Evans, D.N., Green, D.V., Hopewell, P.L., Humber, D.C. J. Med. Chem. (1995) [Pubmed]
  4. Type I benzophenone-mediated nucleophilic reaction of 5'-amino-2',5'-dideoxyguanosine. A model system for the investigation of photosensitized formation of DNA-protein cross-links. Morin, B., Cadet, J. Chem. Res. Toxicol. (1995) [Pubmed]
  5. Activity-based probes for the proteomic profiling of metalloproteases. Saghatelian, A., Jessani, N., Joseph, A., Humphrey, M., Cravatt, B.F. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  6. Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression. Balasubramanyam, K., Altaf, M., Varier, R.A., Swaminathan, V., Ravindran, A., Sadhale, P.P., Kundu, T.K. J. Biol. Chem. (2004) [Pubmed]
  7. Presenilin-1 and -2 are molecular targets for gamma-secretase inhibitors. Seiffert, D., Bradley, J.D., Rominger, C.M., Rominger, D.H., Yang, F., Meredith, J.E., Wang, Q., Roach, A.H., Thompson, L.A., Spitz, S.M., Higaki, J.N., Prakash, S.R., Combs, A.P., Copeland, R.A., Arneric, S.P., Hartig, P.R., Robertson, D.W., Cordell, B., Stern, A.M., Olson, R.E., Zaczek, R. J. Biol. Chem. (2000) [Pubmed]
  8. Photoaffinity-labeling peptide substrates for farnesyl-protein transferase and the intersubunit location of the active site. Ying, W., Sepp-Lorenzino, L., Cai, K., Aloise, P., Coleman, P.S. J. Biol. Chem. (1994) [Pubmed]
  9. On the Z-E photoisomerization of chiral 2-pentenoate esters: stationary irradiations, laser-flash photolysis studies, and theoretical calculations. García-Expósito, E., González-Moreno, R., Martín-Vilà, M., Muray, E., Rifé, J., Bourdelande, J.L., Branchadell, V., Ortuño, R.M. J. Org. Chem. (2000) [Pubmed]
  10. Photosensitization by fenofibrate. II. In vitro phototoxicity of the major metabolites. Miranda, M.A., Boscá, F., Vargas, F., Canudas, N. Photochem. Photobiol. (1994) [Pubmed]
  11. Photoallergy to benzophenone. Knobler, E., Almeida, L., Ruzkowski, A.M., Held, J., Harber, L., DeLeo, V. Archives of dermatology. (1989) [Pubmed]
  12. Study on the mechanism of photosensitive dermatitis caused by ketoprofen in the guinea pig. Nakazawa, T., Shimo, T., Chikamatsu, N., Igarashi, T., Nagata, O., Yamamoto, M. Arch. Toxicol. (2006) [Pubmed]
  13. Contact and photocontact allergy to ketoprofen. The Belgian experience. Matthieu, L., Meuleman, L., Van Hecke, E., Blondeel, A., Dezfoulian, B., Constandt, L., Goossens, A. Contact Derm. (2004) [Pubmed]
  14. Transglutaminase-catalyzed site-specific conjugation of small-molecule probes to proteins in vitro and on the surface of living cells. Lin, C.W., Ting, A.Y. J. Am. Chem. Soc. (2006) [Pubmed]
  15. Diphenylacetaldehyde-generated excited states promote damage to isolated rat liver mitochondrial DNA, phospholipids, and proteins. Almeida, A.M., Bechara, E.J., Vercesi, A.E., Nantes, I.L. Free Radic. Biol. Med. (1999) [Pubmed]
  16. Scavenging effect of benzophenones on the oxidative stress of skeletal muscle cells. Sun, J.S., Shieh, K.M., Chiang, H.C., Sheu, S.Y., Hang, Y.S., Lu, F.J., Tsuang, Y.H. Free Radic. Biol. Med. (1999) [Pubmed]
  17. Synthesis and structure-activity relationship of 2-aminobenzophenone derivatives as antimitotic agents. Liou, J.P., Chang, C.W., Song, J.S., Yang, Y.N., Yeh, C.F., Tseng, H.Y., Lo, Y.K., Chang, Y.L., Chang, C.M., Hsieh, H.P. J. Med. Chem. (2002) [Pubmed]
  18. Benzodiazepines identified by capillary gas chromatography-mass spectrometry, with specific ion screening used to detect benzophenone derivatives. Jones, C.E., Wians, F.H., Martinez, L.A., Merritt, G.J. Clin. Chem. (1989) [Pubmed]
  19. Dynamic structure of the calmodulin-binding domain of the plasma membrane Ca-ATPase in native erythrocyte ghost membranes. Yao, Y., Gao, J., Squier, T.C. Biochemistry (1996) [Pubmed]
  20. Design, synthesis, and pharmacological evaluation of potent xanthone dicarboxylic acid leukotriene B4 receptor antagonists. Jackson, W.T., Boyd, R.J., Froelich, L.L., Gapinski, D.M., Mallett, B.E., Sawyer, J.S. J. Med. Chem. (1993) [Pubmed]
  21. Endocrine disruptors that deplete glutathione levels in APC promote Th2 polarization in mice leading to the exacerbation of airway inflammation. Kato, T., Tada-Oikawa, S., Takahashi, K., Saito, K., Wang, L., Nishio, A., Hakamada-Taguchi, R., Kawanishi, S., Kuribayashi, K. Eur. J. Immunol. (2006) [Pubmed]
  22. Benzophenone synthase from cultured cells of Centaurium erythraea. Beerhues, L. FEBS Lett. (1996) [Pubmed]
  23. Magnetic field effects on the behavior of radicals in protein and DNA environments. Mohtat, N., Cozens, F.L., Hancock-Chen, T., Scaiano, J.C., McLean, J., Kim, J. Photochem. Photobiol. (1998) [Pubmed]
  24. Photochemical probes of the active site of myosin. Irradiation of trapped 3'-O-(4-benzoyl)benzoyladenosine 5'-triphosphate labels the 50-kilodalton heavy chain tryptic peptide. Mahmood, R., Yount, R.G. J. Biol. Chem. (1984) [Pubmed]
  25. Survey of four different photoreactive moieties for DNA photoaffinity labeling of yeast RNA polymerase III transcription complexes. Tate, J.J., Persinger, J., Bartholomew, B. Nucleic Acids Res. (1998) [Pubmed]
  26. Properties of excited ketyl radicals of benzophenone analogues affected by the size and electronic character of the aromatic ring systems. Sakamoto, M., Cai, X., Fujitsuka, M., Majima, T. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  27. Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus. Gapinski, D.M., Mallett, B.E., Froelich, L.L., Jackson, W.T. J. Med. Chem. (1990) [Pubmed]
  28. Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase. Patricelli, M.P., Cravatt, B.F. Biochemistry (2001) [Pubmed]
  29. Development of a photoreactive parathyroid hormone antagonist to probe antagonist-receptor bimolecular interaction. Bisello, A., Behar, V., Greenberg, Z., Suva, L.J., Rosenblatt, M., Chorev, M. J. Pept. Res. (1999) [Pubmed]
  30. Identification of specific sites involved in ligand binding by photoaffinity labeling of the receptor for the urokinase-type plasminogen activator. Residues located at equivalent positions in uPAR domains I and III participate in the assembly of a composite ligand-binding site. Ploug, M. Biochemistry (1998) [Pubmed]
  31. Structure based design of benzophenone-based non-thiol farnesyltransferase inhibitors. Schlitzer, M. Curr. Pharm. Des. (2002) [Pubmed]
  32. Photoimmobilization of proteins for affinity capture combined with MALDI TOF MS analysis. Janecki, D.J., Broshears, W.C., Reilly, J.P. Anal. Chem. (2004) [Pubmed]
  33. Sulfhydryl-reactive, cleavable, and radioiodinatable benzophenone photoprobes for study of protein-protein interaction. Guo, L.W., Hajipour, A.R., Gavala, M.L., Arbabian, M., Martemyanov, K.A., Arshavsky, V.Y., Ruoho, A.E. Bioconjug. Chem. (2005) [Pubmed]
  34. High-performance liquid chromatography of benzophenone derivatives for the determination of benzodiazepines in clinical emergencies. Violon, C., Pessemier, L., Vercruysse, A. J. Chromatogr. (1982) [Pubmed]
  35. Electron-capture gas chromatography of methadone after oxidation to benzophenone. Hartvig, P., Näslund, B. J. Chromatogr. (1975) [Pubmed]
  36. Further studies on ultraviolet-absorbing hydrogels for intraocular lenses: relationship between concentration of a polymerizable benzophenone, absorption, and extractability. Chirila, T.V., Barrett, G.D., Fletcher, W.A., Russo, A.V., Constable, I.J. Journal of cataract and refractive surgery. (1991) [Pubmed]
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