Sangivamycin

Sangivamycin
Identifiers
	IUPAC name 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide;
CAS Number	18417-89-5;
PubChem CID	14978;
ChemSpider	14261;
UNII	L8YQ8Z3T9T;
ChEBI	CHEBI:85997;
ChEMBL	ChEMBL101892;
ECHA InfoCard	100.162.068
Chemical and physical data
Formula	C12H15N5O5
Molar mass	309.28 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C(=O)N;
	InChI InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1; Key:OBZJZDHRXBKKTJ-JTFADIMSSA-N;

Sangivamycin is a natural product originally isolated from Streptomyces rimosus, which is a nucleoside analogue. It acts as an inhibitor of protein kinase C. It has antibiotic, antiviral and anti-cancer properties and has been investigated for various medical applications, though never approved for clinical use itself. However, a number of related derivatives continue to be researched.[1][2][3][4][5][6][7]

References

Tolman RL, Robins RK, Townsend LB (January 1968). "Pyrrolo[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and Sangivamycin (BA-90912)". Journal of the American Chemical Society. 90 (2): 524–6. doi:10.1021/ja01004a076. PMID 5634627.
De Clercq E, Bernaerts R, Bergstrom DE, Robins MJ, Montgomery JA, Holy A (March 1986). "Antirhinovirus activity of purine nucleoside analogs". Antimicrobial Agents and Chemotherapy. 29 (3): 482–7. doi:10.1128/aac.29.3.482. PMC 180418. PMID 3013084.
Loomis CR, Bell RM (February 1988). "Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C". The Journal of Biological Chemistry. 263 (4): 1682–92. PMID 3338987.
Kučić N, Mahmutefendić H, Lučin P (August 2005). "Inhibition of protein kinases C prevents murine cytomegalovirus replication". The Journal of General Virology. 86 (Pt 8): 2153–2161. doi:10.1099/vir.0.80733-0. PMID 16033962.
Lee SA, Jung M (May 2007). "The nucleoside analog sangivamycin induces apoptotic cell death in breast carcinoma MCF7/adriamycin-resistant cells via protein kinase Cdelta and JNK activation". The Journal of Biological Chemistry. 282 (20): 15271–83. doi:10.1074/jbc.M701362200. PMID 17371872.
Bastea LI, Hollant LM, Döppler HR, Reid EM, Storz P (November 2019). "Sangivamycin and its derivatives inhibit Haspin-Histone H3-survivin signaling and induce pancreatic cancer cell death". Scientific Reports. 9 (1): 16588. doi:10.1038/s41598-019-53223-0. PMC 6851150. PMID 31719634.
Smith HC, et al. Methods of treating and inhibiting ebola virus infection. Patent application CA3040540, Oyagen Inc, 17 May 2018

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[1] Tolman RL, Robins RK, Townsend LB (January 1968). "Pyrrolo[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and Sangivamycin (BA-90912)". Journal of the American Chemical Society. 90 (2): 524–6. doi:10.1021/ja01004a076. PMID 5634627.

[2] De Clercq E, Bernaerts R, Bergstrom DE, Robins MJ, Montgomery JA, Holy A (March 1986). "Antirhinovirus activity of purine nucleoside analogs". Antimicrobial Agents and Chemotherapy. 29 (3): 482–7. doi:10.1128/aac.29.3.482. PMC 180418. PMID 3013084.

[3] Loomis CR, Bell RM (February 1988). "Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C". The Journal of Biological Chemistry. 263 (4): 1682–92. PMID 3338987.

[4] Kučić N, Mahmutefendić H, Lučin P (August 2005). "Inhibition of protein kinases C prevents murine cytomegalovirus replication". The Journal of General Virology. 86 (Pt 8): 2153–2161. doi:10.1099/vir.0.80733-0. PMID 16033962.

[5] Lee SA, Jung M (May 2007). "The nucleoside analog sangivamycin induces apoptotic cell death in breast carcinoma MCF7/adriamycin-resistant cells via protein kinase Cdelta and JNK activation". The Journal of Biological Chemistry. 282 (20): 15271–83. doi:10.1074/jbc.M701362200. PMID 17371872.

[6] Bastea LI, Hollant LM, Döppler HR, Reid EM, Storz P (November 2019). "Sangivamycin and its derivatives inhibit Haspin-Histone H3-survivin signaling and induce pancreatic cancer cell death". Scientific Reports. 9 (1): 16588. doi:10.1038/s41598-019-53223-0. PMC 6851150. PMID 31719634.

[7] Smith HC, et al. Methods of treating and inhibiting ebola virus infection. Patent application CA3040540, Oyagen Inc, 17 May 2018

Sangivamycin

See also

References