Misplaced Pages

Viridicatumtoxin B

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Viridicatumtoxin B
Names
IUPAC name (1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spirotetracene]-9'-carboxamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
InChI
  • InChI=1S/C30H29NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,32-34,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t28-,29-,30+/m0/s1Key: SSOXEPGCLBSNOP-OIFRRMEBSA-N
  • tautomer: InChI=1S/C30H29NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,32,34,36,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t28-,29-,30+/m0/s1Key: WUFPHUQCGWRGKE-OIFRRMEBSA-N
SMILES
  • CC1=CCCC(12Cc3c4c2c(cc(c4c(c5c3C(=O)6(CC(=C(C(=O)6(C5=O)O)C(=O)N)O)O)O)O)OC)(C)C
  • tautomer: CC1=CCCC(12CC3=C4C2=C(C=C(C4=C(C5=C3C(=O)6(CC(=O)C(=C(6(C5=O)O)O)C(=O)N)O)O)O)OC)(C)C
Properties
Chemical formula C30H29NO10
Molar mass 563.559 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Viridicatumtoxin B is a fungus-derived tetracycline-like antibiotic discovered in 2008. It was isolated from small amounts of penicillium fungi. A synthetic structure matching that of natural viridicatumtoxin B makes possible synthetic variants that match or surpass its antibiotic potency.

Analogs lacking a hydroxyl group were even more effective than the original against Gram-positive bacteria.

Concerns about solubility, biodegradation, availability and other issues must be resolved before clinical development begins.

History

The substance was first isolated from the mycelium of liquid fermentation cultures of Penicillium species FR11.

Structure

Based on mass spectrometry and nuclear magnetic resonance data, the substance was originally thought to be the 11a',12'-epoxide, but the structure was later revised.

Effects

Viridicatumtoxin B inhibited the growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus with a minimum inhibitory concentration of 0.5 μg/ml. That effect is similar to that of vancomycin, but 8 to 64 times greater than that of tetracycline.

Total synthesis

A complete total synthesis of viridicatumtoxin B, in racemic form, was completed in 2013 by the group of K. C. Nicolaou.

See also

References

  1. ^ "Synthesis produces new antibiotic". Research & Development. 28 August 2014. Retrieved 2015-10-09.
  2. ^ Zheng, C. J.; Yu, H. E.; Kim, E. H.; Kim, W. G. (2008). "Viridicatumtoxin B, a new anti-MRSA agent from Penicillium sp. FR11". The Journal of Antibiotics. 61 (10): 633–7. doi:10.1038/ja.2008.84. PMID 19168978.
  3. ^ Nicolaou, K. C.; Hale, Christopher R. H.; Nilewski, Christian; Ioannidou, Heraklidia A.; Elmarrouni, Abdelatif; Nilewski, Lizanne G.; Beabout, Kathryn; Wang, Tim T.; Shamoo, Yousif (2014). "Total Synthesis of Viridicatumtoxin B and Analogues Thereof: Strategy Evolution, Structural Revision, and Biological Evaluation". Journal of the American Chemical Society. 136 (34): 12137–60. doi:10.1021/ja506472u. PMC 4210137. PMID 25317739.
  4. Nicolaou, K. C.; Nilewski, Christian; Hale, Christopher R. H.; Ioannidou, Heraklidia A.; Elmarrouni, Abdelatif; Koch, Lizanne G. (2013). "Total Synthesis and Structural Revision of Viridicatumtoxin B". Angewandte Chemie International Edition. 52 (33): 8736–41. doi:10.1002/anie.201304691. PMC 3835450. PMID 23893651.


Stub icon

This systemic antibiotic-related article is a stub. You can help Misplaced Pages by expanding it.

Categories:
Viridicatumtoxin B Add topic