Sangivamycin

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]

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
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.162.068
Chemical and physical data
FormulaC12H15N5O5
Molar mass309.28 g·mol−1
3D model (JSmol)
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

Oyagen, a biotechnology company, has been developing sangivamycin or OYA1, which showed efficacy against Ebola infections,[8] as a broad spectrum antiviral for COVID-19.[9][10] Tonix Pharmaceuticals licensed OYA1 from Oyagen in April 2021 to develop it for the treatment of COVID-19 and it is now called TNX-3500. [11][12][13]

See also

References
  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
  8. Bennett RP, Finch CL, Postnikova EN, Stewart RA, Cai Y, Yu S, et al. (December 2020). "A Novel Ebola Virus VP40 Matrix Protein-Based Screening for Identification of Novel Candidate Medical Countermeasures". Viruses. 13 (1): 52. doi:10.3390/v13010052. PMC 7824103. PMID 33396288.
  9. Philippidis A (2020-05-18). "OyaGen - OYA1". GEN - Genetic Engineering and Biotechnology News. Retrieved 2021-04-22.
  10. Philippidis A (2020-03-18). "Catching Up to Coronavirus: Top 60 Treatments in Development". GEN - Genetic Engineering and Biotechnology News. Retrieved 2021-04-22.
  11. "Tonix hopes for COVID-19 drug tonic as it pens OyaGen antiviral pact". FierceBiotech. Retrieved 2021-04-22.
  12. "BioWorld Science". science.bioworld.com. Retrieved 2021-04-22.
  13. "Tonix Seeks to Advance OyaGen's COVID-19 Treatment Under New Global Licensing Deal". BioSpace. Retrieved 2021-04-22.
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