High impact information on NSC97094

• Compound I of Mb mutants (Mb-I), a ferryl species (Fe(IV)=O) paired with a porphyrin radical cation, is readily prepared by the reaction with a nearly stoichiometric amount of m-chloroperbenzoic acid [1].
• However, PGHS activity in L9 cells increased to the level in S1 cells upon the addition of the hydroperoxide 15-hydroperoxyeicosatetraenoic acid or of 3-chloroperoxybenzoic acid [2].
• We present a kinetic study of the formation of the key intermediate compound I by probing the role of the conserved distal amino acid triad Arg-Trp-His of a recombinant catalase-peroxidase in its reaction with hydrogen peroxide, peroxoacetic acid, and m-chloroperbenzoic acid [3].
• Although we have recently observed compound I of the F43H/H64L Mb mutant, F43H and wild type Mb react with m-chloroperbenzoic acid to give Mb-II without any accumulation of Mb-I [4].
• The second order rate constants for compound I formation are (5.9 +/- 0.1) x 10(4) M-1 s-1 using t-butyl hydroperoxide as the oxidant, (2.5 +/- 0.1) x 10(6) M-1 s-1 for ethyl hydroperoxide and (5.1 +/- 0.6) x 10(7) M-1 s-1 for m-chloroperoxybenzoic acid at pH 7.0, 6.7 +/- 0.2 degrees C, and ionic strength 0.1 M [5].

Biological context of NSC97094

• On the other hand, 3-chloroperbenzoic acid has been found to support a copper complex-insensitive 7-ethoxycoumarin dealkylation [6].
• Treatment of mexicanin A (9) with m-chloroperbenzoic acid gave, in addition to the 1,2-epoxy derivative 10, 1-alpha-hydroxyhelenalin (11) which furnished an acetate (12) upon acetylation [7].
• [reaction: see text] Reactive cyclic oxocarbenium ions, generated in situ from internal hemiketals, undergo Baeyer-Villiger oxidation upon exposure to m-chloroperbenzoic acid leading, after hydrolysis of the resultant lactones, to acyclic fragments for use in natural product synthesis [8].
• A simple Ni(II)(TPA) complex [TPA = tris(2-pyridylmethyl)amine] has been demonstrated to act as an efficient turnover catalyst for alkane hydroxylation with m-CPBA (m-chloroperbenzoic acid), in which contribution of a NiO(+) (nickel-oxo) type active oxygen species is suggested [9].
• The kinetics of Compound I formation was also followed with peracetic acid, ethylhydroperoxide, and m-chloroperbenzoic acid as electron acceptors [10].

Anatomical context of NSC97094

• The effects of oxygen active species (.OH and O(2)(.-) radicals) photogenerated by the novel photosensitizer m-chloroperbenzoic acid (m-CPBA) on human erythrocyte integrity and stability were studied [11].

Associations of NSC97094 with other chemical compounds

• Distal histidine mutants of sperm whale Mb (His-64 --> Ala, Ser, and Leu) afford an apparent intermediate followed by the formation of a ferryl heme (Mb-II) in the reaction with m-chloroperbenzoic acid [4].
• Oxidation of this sterol with m-chloroperbenzoic acid followed by hydrolysis and acetylation furnished 5 alpha-cholest-7-ene-3 beta,5,6 alpha-triol 3,6-diacetate (2) [12].
• The final "global' phosphorylation of the peptide resins was accomplished using di-tert-butyl N, N-diethylphosphoramidite followed by m-chloroperoxybenzoic acid oxidation of the resultant di-t-butyl phosphite triester intermediate [13].
• The kinetics of the soluble and immobilised forms of the enzyme were investigated for the catalysed oxidation of potassium ferrocyanide in the presence of H2O2 and m-chloroperoxybenzoic acid [14].
• Ability of m-chloroperoxybenzoic acid to induce the ornithine decarboxylase marker of skin tumor promotion and inhibition of this response by gallotannins, oligomeric proanthocyanidins, and their monomeric units in mouse epidermis in vivo [15].

Gene context of NSC97094

• The reaction with hydrogen peroxide converted the heme of the heme oxygenase-2 fragment complex into a verdoheme-like intermediate, while the reaction with m-chloroperbenzoic acid yielded a oxoferryl species [16].
• Whereas the O-O bond of hydroperoxides containing an electron-donating tert-alkyl group is cleaved homolytically, an electron-withdrawing substituent such as an acyl group in m-chloroperoxybenzoic acid (m-CPBA) facilitates O-O bond heterolysis [17].
• At pH 7 and 15 degrees C, the rate constant of the reaction between 3-chloroperoxybenzoic acid and ferric MPO was similar to that with hydrogen peroxide (1.8x10(7) M(-1) s(-1) and 1.4x10(7) M(-1) s(-1), respectively) [18].
• Treatment of Delta 4-3-ketosteroids with m-chloroperbenzoic acid at 0 degrees C produced the corresponding steroidal seven-membered A-ring epoxy lactones [19].
• m-Chloroperoxybenzoic acid (CPBA) was tested for its ability to induce the ornithine decarboxylase (ODC) marker of skin tumor promotion [15].

Analytical, diagnostic and therapeutic context of NSC97094

• Titrations of 2-thioflavins with m-chloroperoxybenzoic acid also yield the same blue flavins with consumption of 1 eq of peracid [20].
• Epoxidation of 14 with m-chloroperbenzoic acid gave 1,beta hydroxyhelenalin (19) and a mixture of monoepoxides (17 and 18) which yielded 19 and 11 upon silica gel chromatography [7].
• Upon extraction, both C0 and C1 were oxidized to C2 by m-chloroperoxybenzoic acid, and C2 was determined by liquid chromatography (LC) [21].

References