Rebeccamycin
Rebeccamycin structure
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Common Name | Rebeccamycin | ||
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| CAS Number | 93908-02-2 | Molecular Weight | 570.37800 | |
| Density | 1.87g/cm3 | Boiling Point | N/A | |
| Molecular Formula | C27H21Cl2N3O7 | Melting Point | N/A | |
| MSDS | Chinese USA | Flash Point | N/A | |
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Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM.
J. Biol. Chem. 283(33) , 22628-36, (2008) The 2.65-angstroms crystal structure of the rebeccamycin 4'-O-methyltransferase RebM in complex with S-adenosyl-l-homocysteine revealed RebM to adopt a typical S-adenosylmethionine-binding fold of small molecule O-methyltransferases (O-MTases) and display a w... |
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Natural product diversification using a non-natural cofactor analogue of S-adenosyl-L-methionine.
J. Am. Chem. Soc. 128(9) , 2760-1, (2006) Adenosine analogues bearing either 5'-aziridine or 5'-N-mustard electrophiles are methyltransferase-dependent DNA alkylating agents. We present here a novel synthetic cofactor bearing a pendant 5'-amino acid N-mustard. Unlike previously studied synthetic cofa... |
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Engineering biosynthetic pathways to generate antitumor indolocarbazole derivatives.
J. Ind. Microbiol. Biotechnol. 33(7) , 560-8, (2006) The indolocarbazole family of natural products is a source of lead compounds with potential therapeutic applications in the treatment of cancer and neurodegenerative disorders. Rebeccamycin and staurosporine are two members of this family, which are produced ... |
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Flavin redox chemistry precedes substrate chlorination during the reaction of the flavin-dependent halogenase RebH.
Biochemistry 45(25) , 7904-12, (2006) The flavin-dependent halogenase RebH catalyzes chlorination at the C7 position of tryptophan as the initial step in the biosynthesis of the chemotherapeutic agent rebeccamycin. The reaction requires reduced FADH(2) (provided by a partner flavin reductase), ch... |
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Rebeccamycin derivatives as dual DNA-damaging agents and potent checkpoint kinase 1 inhibitors.
Mol. Pharmacol. 74(6) , 1620-9, (2008) Rebeccamycin is an indolocarbazole class inhibitor of topoisomerase I. In the course of structure-activity relationship studies on rebeccamycin derivatives, we have synthesized analogs with the sugar moiety attached to either one or both indole nitrogens. Som... |
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Molecular cloning, sequence analysis and functional characterization of the gene cluster for biosynthesis of K-252a and its analogs.
Mol. Biosyst. 5(10) , 1180-91, (2009) Among the indolocarbazole alkaloids of antitumor antibiotics, K-252a represents a structurally unique indolocarbazole glycoside and exhibits potent neuroprotective and broad anticancer activities. K-252a consists of K-252c and the unusual dihydrostreptose moi... |
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Synthesis and biological activities of isogranulatimide analogues.
Bioorg. Med. Chem. 15(17) , 5965-80, (2007) The synthesis of new isogranulatimide analogues, their inhibitory activities toward the Checkpoint 1 kinase (Chk1), and their in vitro cytotoxicities toward four tumor cell lines (one murine L1210 leukemia, and three human cell lines: DU145 prostate carcinoma... |
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A concise approach to 1,11-didechloro-6-methyl-4'-O-demethyl rebeccamycin and its binding to human serum albumin: fluorescence spectroscopy and molecular modeling method.
Bioorg. Med. Chem. 16(16) , 7615-21, (2008) 1,11-Didechloro-6-methyl-4'-O-demethyl rebeccamycin (JDC-108), a rebeccamycin analog possessing potent anti-tumor activities, was prepared via a concise one-pot strategy in good yield. The interaction between JDC-108 and human serum albumin (HSA) was studied ... |
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Synthesis, biological evaluation, and molecular modeling studies of rebeccamycin analogues modified in the carbohydrate moiety.
ChemMedChem 3(2) , 266-79, (2008) A new series of indolocarbazole glycosides containing disaccharides were synthesized and their in vitro antiproliferative activity was evaluated against three human cancer cell lines (A2780, H460, and GLC4). Cytotoxicity appeared to be remarkably affected by ... |
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Characterization and functional modification of StaC and RebC, which are involved in the pyrrole oxidation of indolocarbazole biosynthesis.
Biosci. Biotechnol. Biochem. 75(11) , 2184-93, (2011) The diversity of indolocarbazole natural products results from the differences in oxidation states of the pyrroline ring moiety. In the biosynthetic pathways for staurosporine and rebeccamycin, two homologous enzymes having 64% identity, StaC and RebC, are re... |