Rebeccamycin

Names

[ 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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.