CAS 93908-02-2|Rebeccamycin

Introduction：Basic information about CAS 93908-02-2|Rebeccamycin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Rebeccamycin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles33
7. Synonyms

Common Name	Rebeccamycin
CAS Number	93908-02-2	Molecular Weight	570.37800
Density	1.87g/cm3	Boiling Point	/
Molecular Formula	C₂₇H₂₁Cl₂N₃O₇	Melting Point	/
MSDS	ChineseUSA	Flash Point	/

Names

Name	rebeccamycin
Synonym	More Synonyms

Rebeccamycin BiologicalActivity

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 >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseSignaling 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
InChIKey	QEHOIJJIZXRMAN-QZQSLCQPSA-N
SMILES	COC1C(CO)OC(n2c3c(Cl)cccc3c3c4c(c5c6cccc(Cl)c6[nH]c5c32)C(=O)NC4=O)C(O)C1O

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

Articles33

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...

Synonyms

AmbotzLS-1199

MFCD01718312

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