レベッカマイシン

レベッカマイシン
IUPAC命名法による物質名
	IUPAC名 1,11-dichloro-12-(4-O-methyl-β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione;
データベースID
CAS番号;	93908-02-2
ATCコード	none
PubChem	CID: 73110
ChemSpider	65891
ChEBI	CHEBI:135511
ChEMBL	CHEMBL370100
別名	7,10-dichloro-8-(3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)-8,9-dihydro-1H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione
化学的データ
化学式	C27H21Cl2N3O7
分子量	570.38
	SMILES O=C1c5c(C(=O)N1)c3c2cccc(Cl)c2nc3c6n(c4c(Cl)cccc4c56)[C@@H]7O[C@@H]([C@@H](OC)[C@H](O)[C@H]7O)CO;
	InChI InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1; Key:QEHOIJJIZXRMAN-QZQSLCQPSA-N;
	テンプレートを表示

レベッカマイシン（rebeccamycin）は、スタウロスポリンと構造的に類似している、Streptomyces sp.から単離された弱いトポイソメラーゼI阻害剤である^[1]^[2]^[3]^[4]。プロテインキナーゼあるいはトポイソメラーゼIIに対する阻害活性はほとんど示さない^[5]。In vitroで顕著な抗腫瘍作用を示す（IC₅₀: 480 nM, マウスB16メラノーマ細胞、500 nM, P388白血病細胞）^[1]。

Lechevalieria aerocolonigenesから単離され、1985年に報告された^[6]。

脚注

^ ^a ^b Bush JA, Long BH, Catino JJ, Bradner WT, Tomita K (1987). “Production and biological activity of rebeccamycin, a novel antitumor agent”. J. Antibiot. (Tokyo). 40 (5): 668-678. doi:10.7164/antibiotics.40.668. PMID 3112080.
^ Anizon F, Belin L, Moreau P, Sancelme M, Voldoire A, Prudhomme M, Ollier M, Sevère D, Riou JF, Bailly C, Fabbro D, Meyer T (1997). “Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group”. J. Med. Chem. 40 (21): 3456-3465. doi:10.1021/jm9702084. PMID 9341921.
^ Bailly C, Riou JF, Colson P, Houssier C, Rodrigues-Pereira E, Prudhomme M (1997). “DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin”. Biochemistry 36 (13): 3917-3929. doi:10.1021/bi9624898. PMID 9092822.
^ Bailly C, Qu X, Graves DE, Prudhomme M, Chaires JB (1999). “Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition”. Chem. Biol. 6 (5): 277-286. doi:10.1016/S1074-5521(99)80073-8. PMID 10322124.
^ Prudhomme, M. (2000). “Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents”. Curr. Med. Chem. 7: 1189–1212. doi:10.2174/0929867003374138.
^ D.E. Nettleton, T.W. Doyle, B. Krishnan, G.K. Matsumoto, J. Clardy (1985). “Isolation and structure of rebeccamycin - a new antitumor antibiotic from Nocardia aerocoligenes”. Tetrahedron Lett. 26 (34): 4011–4014. doi:10.1016/S0040-4039(00)89280-1.

この項目は、化学に関連した書きかけの項目です。この項目を加筆・訂正などしてくださる協力者を求めています（プロジェクト:化学／Portal:化学）。

この項目は、薬学に関連した書きかけの項目です。この項目を加筆・訂正などしてくださる協力者を求めています（プロジェクト:薬学／Portal:医学と医療/Portal:化学）。

[JA-1] Bush JA, Long BH, Catino JJ, Bradner WT, Tomita K (1987). “Production and biological activity of rebeccamycin, a novel antitumor agent”. J. Antibiot. (Tokyo). 40 (5): 668-678. doi:10.7164/antibiotics.40.668. PMID 3112080.

[2] Anizon F, Belin L, Moreau P, Sancelme M, Voldoire A, Prudhomme M, Ollier M, Sevère D, Riou JF, Bailly C, Fabbro D, Meyer T (1997). “Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group”. J. Med. Chem. 40 (21): 3456-3465. doi:10.1021/jm9702084. PMID 9341921.

[3] Bailly C, Riou JF, Colson P, Houssier C, Rodrigues-Pereira E, Prudhomme M (1997). “DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin”. Biochemistry 36 (13): 3917-3929. doi:10.1021/bi9624898. PMID 9092822.

[4] Bailly C, Qu X, Graves DE, Prudhomme M, Chaires JB (1999). “Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition”. Chem. Biol. 6 (5): 277-286. doi:10.1016/S1074-5521(99)80073-8. PMID 10322124.

[5] Prudhomme, M. (2000). “Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents”. Curr. Med. Chem. 7: 1189–1212. doi:10.2174/0929867003374138.

[6] D.E. Nettleton, T.W. Doyle, B. Krishnan, G.K. Matsumoto, J. Clardy (1985). “Isolation and structure of rebeccamycin - a new antitumor antibiotic from Nocardia aerocoligenes”. Tetrahedron Lett. 26 (34): 4011–4014. doi:10.1016/S0040-4039(00)89280-1.

[1]

[2]

[3]

[4]

[5]

[6]