Rebeccamycin - CAS 93908-02-2

Rebeccamycin - CAS 93908-02-2 Catalog number: BADC-00842

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Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II.

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BADC-00842 -- $--
Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II.
5H-Indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-beta-D-glucopyranosyl)-; 1,11-dichloro-12-(4-O-methyl-beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione; (Rebeccamycin)1,11-dichloro-12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione; 1,11-dichloro-12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione; 1,11-dichloro-12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione(rebeccamycin); 1,11-dichloro-12-[3,4-dihydroxy-6-hydroxymethyl-5-methoxy-(2R,3R,4S,5R,6R)-tetrahydro-2H-2-pyranyl]-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione; dichloro-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxy-tetrahydropyran-2-yl][?]dione
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1.87 g/cm3
10 mm in DMSO
Melting Point
326-330°C (dec.)
Index Of Refraction
In Vivo
Rebeccamycin (2-256 mg/kg; i.p.; daily for 9 days) prolongs survival in B16 melanoma, L1210 leukemia. Animal Model: CDF1 mice (B16 melanoma, L1210 leukemia) Dosage: 2, 4, 8, 16, 32, 64, 128, 256 mg/kg Administration: I.p.; daily for 9 days Result: Prolongation of survival of the mice at dose levels ranging from 8 to 256 mg/kg.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT00086983Unspecified Adult Solid Tumor, Protocol SpecificPhase 12013-01-10National Cancer Institute (NCI)Terminated
NCT00004189LymphomaPhase 12013-02-11National Cancer Institute (NCI)Completed
NCT00005817Male Breast CancerPhase 22013-02-01National Cancer Institute (NCI)Completed
NCT00005085Colorectal CancerPhase 22013-02-11National Cancer Institute (NCI)Completed
NCT00006262Ovarian CancerPhase 22012-06-11Northwestern UniversityTerminated (Unable to accrue patients to the study.)
Lechevalieria sp.
Dull Yellow Lyophilisate
Shelf Life
0-4℃ for short term (days to weeks), or -20℃ for long term (months).
Room temperature, or blue ice upon request.
Store at -20 °C, keep in dry and avoid sunlight.
1. Macroparticle-enhanced cultivation of Lentzea aerocolonigenes: Variation of mechanical stress and combination with lecithin supplementation for a significantly increased rebeccamycin production
Kathrin Schrinner, Kristin Althof, Friederike A Schwarzer, Jana Niebusch, Arno Kwade, Anna Dinius, Marcel Schrader, Rainer Krull, Paul-Frederik Nowka Biotechnol Bioeng . 2021 Oct;118(10):3984-3995. doi: 10.1002/bit.27875.
The actinomycete Lentzea aerocolonigenes produces the antitumor antibiotic rebeccamycin. In previous studies the rebeccamycin production was significantly increased by the addition of glass beads during cultivation in different diameters between 0.5 and 2 mm and the induced mechanical stress by the glass beads was proposed to be responsible for the increased production. Thus, this study was conducted to be a systematic investigation of different parameters for macroparticle addition, such as bead diameter, concentration, and density (glass and ceramic) as well as shaking frequency, for a better understanding of the particle-induced stress on L. aerocolonigenes. The induced stress for optimal rebeccamycin production can be estimated by a combination of stress energy and stress frequency. In addition, the macroparticle-enhanced cultivation of L. aerocolonigenes was combined with soy lecithin addition to further increase the rebeccamycin concentration. With 100 g L-1glass beads in a diameter of 969 µm and 5 g L-1soy lecithin a concentration of 388 mg L-1rebeccamycin was reached after 10 days of cultivation, which corresponds to the highest rebeccamycin concentrations achieved in shake flask cultivations of L. aerocolonigenes stated in literature so far.
2. A Rebeccamycin Analog Provides Plasmid-Encoded Niche Defense
Antonio C Ruzzini, Jon Clardy, Ethan B Van Arnam, Clarissa S Sit, Cameron R Currie J Am Chem Soc . 2015 Nov 18;137(45):14272-4. doi: 10.1021/jacs.5b09794.
Bacterial symbionts of fungus-growing ants occupy a highly specialized ecological niche and face the constant existential threat of displacement by another strain of ant-adapted bacteria. As part of a systematic study of the small molecules underlying this fraternal competition, we discovered an analog of the antitumor agent rebeccamycin, a member of the increasingly important indolocarbazole family. While several gene clusters consistent with this molecule's newly reported modification had previously been identified in metagenomic studies, the metabolite itself has been cryptic. The biosynthetic gene cluster for 9-methoxyrebeccamycin is encoded on a plasmid in a manner reminiscent of plasmid-derived peptide antimicrobials that commonly mediate antagonism among closely related Gram-negative bacteria.
3. Rebeccamycin analogues as anti-cancer agents
Michelle Prudhomme Eur J Med Chem . 2003 Feb;38(2):123-40. doi: 10.1016/s0223-5234(03)00011-4.
Rebeccamycin, a microbial metabolite possessing a maleimide indolo[2,3-a]carbazole framework with a carbohydrate moiety attached to one of the indole nitrogens, is a well-known topoisomerase I inhibitor. This review reports the various total syntheses of rebeccamycin and structure-activity relationship studies on rebeccamycin analogues. Rebeccamycin analogues were prepared either by semi-synthesis from the natural metabolite or by total synthesis. Different families of rebeccamycin analogues were obtained by modifications at the imide heterocycle, dechlorination and substitutions on the indole moieties, modifications of the sugar residue, construction of dimers, coupling the sugar unit to the second indole nitrogen, changing indolo[2,3-a]carbazole skeleton to indolo[2,3-c]carbazole, replacing one or both indole moieties by 7-azaindole units. The biological activities of the rebeccamycin analogues are described. According to their chemical structure, the analogues can inhibit topoisomerase I and/or kinases. From the structure-activity relationships, some important rules were established. Several compounds exhibit stronger antiproliferative activities than the natural metabolite with IC(50) values in the nanomolar range. Some analogues, especially those possessing azaindole moieties, are much more selective than rebeccamycin toward the tumour cell lines tested.

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