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NSC 65346

NSC 65346用途

Sangivamycin(NSC 65346)是一种核苷类似物,是一种Ki为10μM的蛋白激酶C(PKC)的有效抑制剂。Sangivamycin对多种人类癌症具有有效的抗增殖活性[1][2]。

NSC 65346名称

[ CAS 号 ]:
18417-89-5

[ 中文名 ]:
桑霉素

[ 英文名 ]:
Sangivamycin

[中文别名 ]:

桑吉瓦霉素

[英文别名 ]:

7-Carboxamido-7-deazaadenosine
7-DEAZA-7-CARBAMOYLADENOSINE
7-DEAZAADENOSINE-7-CARBOXAMIDE
SANGIVAMYCIN

NSC 65346生物活性

[ 描述 ]:

Sangivamycin(NSC 65346)是一种核苷类似物,是一种Ki为10μM的蛋白激酶C(PKC)的有效抑制剂。Sangivamycin对多种人类癌症具有有效的抗增殖活性[1][2]。

[ 相关类别 ]:

信号通路 >> 表观遗传学 >> PKC

研究领域 >> 癌症

信号通路 >> 细胞周期/DNA损伤 >> 核苷抗代谢药/类似物

信号通路 >> TGF-beta/Smad 信号通路 >> PKC

[体外研究]

Sangivamycin对药物敏感的MCF7/野生型(WT)细胞和对多药耐药的MCF7/阿霉素耐药(ADR)人乳腺癌细胞具有不同的抗肿瘤作用,导致细胞大量凋亡[2]。Sangivamycin(0.3μM；0-72小时)显示出几乎最大的细胞杀伤作用(对于MCF7/ADR)或细胞抑制作用(对于MCF7/WT)[2]。桑格霉素激活MCF7/ADR细胞中的半胱天冬酶。当MCF7/ADR细胞暴露于桑格霉素(0.3μM；)时,48小时内检测到大量层粘连蛋白a裂解为28 kDa片段[2]。

[参考文献]

[1]. Loomis CR, Bell RM. Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. J Biol Chem. 1988;263(4):1682-1692.

[2]. Lee SA, et al. The nucleoside analog sangivamycin induces apoptotic cell death in breast carcinoma MCF7/adriamycin-resistant cells via protein kinase Cdelta and JNK activation. J Biol Chem. 2007;282(20):15271-15283.

NSC 65346物理化学性质

[ 沸点 ]:
880.6ºC at 760 mmHg

[ 分子式 ]:
C₁₂H₁₅N₅O₅

[ 分子量 ]:
309.28

[ 闪点 ]:
486.4ºC

[ 精确质量 ]:
327.11800

[ PSA ]:
178.97000

[ 外观性状 ]:
固体

[ 蒸汽压 ]:
3.3E-33mmHg at 25°C

[ 储存条件 ]:
2-8°C，密封，干燥

NSC 65346毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY9355000

CHEMICAL NAME :: 7H-Pyrrolo(2,3-d)pyrimidine-5-carboxamide, 4-amino-7-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 18417-89-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C12-H15-N5-O5

MOLECULAR WEIGHT :: 309.32

WISWESSER LINE NOTATION :: T56 BN GN INJ FZ HVZ I- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Cells - not otherwise specified

DOSE/DURATION :: 500 nmol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 41,1784,1981

NSC 65346安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H300-H310-H330

[ 警示性声明 ]:
P260-P264-P280-P284-P302 + P350-P310

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T+

[ 风险声明 (欧洲) ]:
26/27/28

[ 危险品运输编码 ]:
UN 2811 6.1/PG 2

[ RTECS号 ]:
UY9355000

NSC 65346上下游产品

NSC 65346上游产品

NSC 65346下游产品

NSC 65346文献

Synthesis and in vitro antitumor activity of some amino-deoxy 7-hexofuranosylpyrrolo[2,3-d]pyrimidines.

Carbohydr. Res. 308(3-4) , 319-28, (1998)

7-(6-amino-6-deoxy-beta-D-glucofuranosyl)-5-cyanopyrrolo[2,3 -d]pyrimidine (22) and 7-(3-amino-methyl-3-deoxy-beta-D-allofuranosyl)-5- cyanopyrrolo[2,3-d]pyrimidine (28) were synthesized by sequential...

Kinetics and localization of the phosphorylation of rhodopsin by protein kinase C.

J. Biol. Chem. 270(12) , 6710-7, (1995)

Protein kinase C isolated from retina catalyzes the stoichiometric phosphorylation of bovine rhodopsin. Enzymological studies using receptor in rod outer segment membranes stripped of peripheral prote...

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.

Carbohydr. Res. 331(1) , 77-82, (2001)

Syntheses of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides are reported. Treatment of pyranulose glycoside with aminoguanidine in acetic acid gave the corresponding semicarbazone in 96% yield. The ring ...

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