Sangivamycin

Last updated
Sangivamycin
Sangivamycin.svg
Identifiers
  • 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 InfoCard 100.162.068 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H15N5O5
Molar mass 309.282 g·mol−1
3D model (JSmol)
  • 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=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]

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] In July 2022, Tonix announced that it was terminating development of TNX-3500, an antiviral inhibitor of SARS-CoV-2, and the associated licence agreement with OyaGen, Inc. was expected to be terminated, effective September 20, 2022. [14]

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. doi: 10.1016/S0021-9258(19)77930-7 . 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. Bibcode:2019NatSR...916588B. 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. 19 April 2021. 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.
  14. ↑ Tonix Pharmaceuticals Holding Corp. (Filer) CIK: 0001430306 (30 July 2024). "Form 424B5 - Prospectus [Rule 424(b)(5)]". www.sec.gov. Retrieved 2025-04-10.
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