Frenolicin B is an antibiotic and antitumor agent with the molecular formula C18H16O6 which is produced by the bacterium Streptomyces roseofulvus.[2][1][3] Frenolicin B is a selective inhibitor of glutaredoxin 3 and peroxiredoxin 1.[4][5]
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IUPAC name
(11R,15R,17R)-4-Hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione[1]
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3D model (JSmol)
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6436493 | |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C18H16O6 | |
Molar mass | 328.320 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References
edit- ^ a b "Frenolicin B". Pubchem.ncbi.NLM.nih.gov.
- ^ Bycroft, Barrie W.; Payne, David J. (9 August 2013). Dictionary of Antibiotics and Related Substances: with CD-ROM, Second Edition. CRC Press. p. 845. ISBN 978-1-4822-8215-3.
- ^ Iwai, Yuzuru; Kora, Akiko; Takahashi, Yoko; Hayashi, Takako; Awaya, Juichi; Masuma, Rokurou; Oiwa, Ruiko; Omura, Satoshi (1978). "Production of deoxyfrenolicin and a new antibiotic, frenolicin B by Streptomyces roseofulvus strain AM-3867". The Journal of Antibiotics. 31 (10): 959–965. doi:10.7164/antibiotics.31.959. PMID 711620.
- ^ Huang, Canhua; Zhang, Yuanyuan (25 April 2021). Oxidative Stress: Human Diseases and Medicine. Springer Nature. p. 249. ISBN 978-981-16-0522-2.
- ^ Ye, Q; Zhang, Y; Cao, Y; Wang, X; Guo, Y; Chen, J; Horn, J; Ponomareva, LV; Chaiswing, L; Shaaban, KA; Wei, Q; Anderson, BD; St Clair, DK; Zhu, H; Leggas, M; Thorson, JS; She, QB (21 March 2019). "Frenolicin B Targets Peroxiredoxin 1 and Glutaredoxin 3 to Trigger ROS/4E-BP1-Mediated Antitumor Effects". Cell Chemical Biology. 26 (3): 366–377.e12. doi:10.1016/j.chembiol.2018.11.013. PMC 6557261. PMID 30661989.
Further reading
edit- Fitzgerald, Jay Thomas (2012). Engineering of Biosynthetic Pathways to the Type II Polyketides Frenolicin B and A-74528. Stanford University.
- ApSimon, John (16 April 1992). The Total Synthesis of Natural Products, Volume 8. John Wiley & Sons. p. 345. ISBN 978-0-471-54507-1.
- Negishi, Ei-ichi; Meijere, Armin de (24 November 2003). Handbook of Organopalladium Chemistry for Organic Synthesis. John Wiley & Sons. p. 2385. ISBN 978-0-471-47381-7.