Sangivamycin

[Description]:

Sangivamycin (NSC 65346), a nucleoside analog, is a potent inhibitor of protein kinase C (PKC) with an Ki of 10 μM. Sangivamycin has potent antiproliferative activity against a variety of human cancers[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Signaling Pathways >> TGF-beta/Smad >> PKC

[In Vitro]

Sangivamycin has differential antitumor effects in drug-sensitive MCF7/wild type (WT) cells, causing growth arrest, and in multidrug-resistant MCF7/adriamycin-resistant (ADR) human breast carcinoma cells, causing massive apoptotic cell death[2]. Sangivamycin (0.3 μM; 0-72 hours), shows almost maximal cytocidal (for MCF7/ADR) or cytostatic (for MCF7/WT) effects[2]. Sangivamycin activates caspases in MCF7/ADR cells. Upon exposure of MCF7/ADR cells to Sangivamycin (0.3 μM;), a vast amount of cleavage of lamin A to a 28-kDa fragment is detected within 48 hours[2].

[References]

[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.

[ Boiling Point ]:
880.6ºC at 760 mmHg

[ Molecular Formula ]:
C₁₂H₁₅N₅O₅

[ Molecular Weight ]:
309.28

[ Flash Point ]:
486.4ºC

[ Exact Mass ]:
327.11800

[ PSA ]:
178.97000

[ Vapour Pressure ]:
3.3E-33mmHg at 25°C

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

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H310-H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-P310

[ Personal Protective Equipment ]:
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

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28

[ RIDADR ]:
UN 2811 6.1/PG 2

[ RTECS ]:
UY9355000

Precursor

DownStream

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 ...

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Precursor & DownStream

Precursor

DownStream

Articles

Related Compounds