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Rebeccamycin

Names

[ CAS No. ]:
93908-02-2

[ Name ]:
Rebeccamycin

[Synonym ]:
AmbotzLS-1199
MFCD01718312

Biological Activity

[Description]:

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[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase
Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin

[Target]

Topoisomerase I

Traditional Cytotoxic Agents


[In Vitro]

Rebeccamycin is an antitumor antibiotic produced by the actinomycete Saccharotrix aerocolonigenes with activity against several human tumor cell lines, including A549 (lung adenocarcinoma), HCT-116 (colon carcinoma), and KB (nasopharyngeal carcinoma) [1]. Rebeccamycin shows antibacterial activity against several Gram-positive bacteria, including Staphylococcus aureus and Streptococcus faecalis[3].

[In Vivo]

Rebeccamycin (2-256 mg/kg; i.p.; daily for 9 days) prolongs survival in B16 melanoma, L1210 leukemia[2]. Animal Model: CDF1 mice (B16 melanoma, L1210 leukemia)[2] 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.

[References]

[1]. Merchant J, et al. Phase I clinical and pharmacokinetic study of NSC 655649, a rebeccamycin analogue, given in both single-dose and multiple-dose formats. Clin Cancer Res. 2002 Jul;8(7):2193-201.

[2]. Bush JA, et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78.

[3]. Sánchez C, et al. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31.

Chemical & Physical Properties

[ Density]:
1.87g/cm3

[ Molecular Formula ]:
C27H21Cl2N3O7

[ Molecular Weight ]:
570.37800

[ Exact Mass ]:
569.07600

[ PSA ]:
150.37000

[ Index of Refraction ]:
1.844

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NM3455000
CHEMICAL NAME :
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)-
CAS REGISTRY NUMBER :
93908-02-2
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C27-H21-Cl2-N3-O7
MOLECULAR WEIGHT :
570.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Cells - not otherwise specified
DOSE/DURATION :
3 mg/L
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 40,668,1987

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

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 sma...

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'-ami...

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 stauro...


More Articles