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

• Here we describe a general strategy for creating activity-based proteomic probes for MPs by coupling a zinc-chelating hydroxamate to a benzophenone photocrosslinker, which promote selective binding and modification of MP active sites, respectively [5].
• A novel benzophenone derivative, 2-(2-benzoyl-4-chlorophenoxy)-N-methylpropionamide (Ch-13), induced phenotypic differentiation linked to the inhibition of cell proliferation in human thymic acute lymphoblastic leukemia cell line HPB-ALL cells [1].
• Here we report that garcinol, a polyisoprenylated benzophenone derivative from Garcinia indica fruit rind, is a potent inhibitor of histone acetyltransferases p300 (IC50 approximately 7 microm) and PCAF (IC50 approximately 5 microm) both in vitro and in vivo [6].
• Here, we show that radiolabeled gamma-secretase inhibitors bind to mammalian cell membranes, and a benzophenone analog specifically photocross-links three major membrane polypeptides [7].
• --CAAX motif peptides, which are substrates for isoprenylation, were synthetically derivatized with the light-sensitive benzophenone (Bz) group in order to determine their potential use as catalytic site-directed covalent photocross-linking ligands for one of the enzymes catalyzing protein isoprenylation, farnesyl-protein transferase (FPTase) [8].

Chemical compound and disease context of benzophenone

• Stern-Volmer quenching studies afforded a quantitative measure for the efficiency of the photosensitization processes induced by benzophenone or acetophenone and allowed the determination of the corresponding quenching rate constants [9].
• This behavior can be attributed to the fact that the four compounds retain the benzophenone chromophore present in fenofibrate and is indicative of free radical-mediated photosensitization [10].
• While photoallergy to p-aminobenzoic acid and its esters is well known by dermatologists and the lay public, benzophenone photoallergy is not well appreciated [11].
• These results suggest that the chemical structure of the benzophenone chromophore in KP would be one of the important factors for induction of the photoallergy since both loxoprofen and flurbiprofen do not possess this structure and hence lack photoallergenic potential [12].
• Additional tests with 3 non-steroidal anti-inflammatory drugs without benzophenone structure ibuprofen, naproxen and diclofenac identified only 1 contact allergic reaction to diclofenac [13].

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

• Cross-linking experiments using benzophenone labeled CaM in conjunction with immunoblots using antibodies specific for either CaM or the PM-Ca-ATPase indicate that one molecule of CaM selectively binds one PM-Ca-ATPase polypeptide chain in native erythrocyte ghost membranes [19].
• These compounds represent the major conformationally-restricted analogues of benzophenone dicarboxylic acids previously shown to antagonize the activation of human neutrophils by LTB4 [20].
• In the present study, we have shown that some EDC [benzophenone, p-octylphenol, and tributyltin chloride (TBT)] promoted strong Th2 polarization via suppression and augmentation of Th1 and Th2 development, respectively, from naive CD4(+) T cells primed with anti-CD3 and splenic antigen-presenting cells (APC) [21].
• Benzophenone synthase from cultured cells of Centaurium erythraea [22].
• We have examined the behavior of radical pairs derived by hydrogen abstraction of triplet benzophenone and some of its derivatives from bovine serum albumin, human serum albumin and calf thymus DNA [23].

Associations of benzophenone with other chemical compounds

• 3'-O-(4-Benzoyl)benzoyl-ATP (Bz2ATP), an analog of ATP containing a photoreactive benzophenone moiety, was used as a probe of the ATP binding site of myosin subfragment 1 (SF1) [24].
• We demonstrate labeling of Q-tag fusion proteins both in vitro and on the surface of living mammalian cells with biotin, fluorophores, and a benzophenone photoaffinity probe [14].
• Photoreactive nucleotides containing an aryl azide (AB-dUMP), benzophenone (BP-dUMP), perfluorinated aryl azide (FAB-dUMP) or diazirine (DB-dUMP) coupled to 5-aminoallyl deoxyuridine were incorporated into the SUP4 tRNATyr gene at bp -3/-2 or +11 [25].
• The properties of benzophenone ketyl radical analogues with large aromatic ring systems, such as naphthylphenylketone (2), 4-benzoylbiphenyl (3), and bis(biphenyl-4-yl)methanone (4), were investigated in the excited state by using nanosecond-picosecond two-color two-laser flash photolysis [26].
• Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus [27].

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].

References