Phomopsin A

CHF 240.00
In stock
AG-CN2-0515-C500500 µgCHF 240.00
AG-CN2-0515-M0011 mgCHF 410.00
AG-CN2-0515-M0055 mgCHF 1'640.00
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Product Details
Synonyms PHO-A; NSC 381839
Product Type Chemical
Properties
Formula

C36H45ClN6O12

MW 789.2
CAS 64925-80-0
RTECS SY2593000
Source/Host Chemicals Isolated from Phomopsis leptostromiformis.
Purity Chemicals ≥98% (HPLC, TLC)
Appearance White solid.
Solubility Soluble in DMSO (10mg/ml), ethanol, methanol (5mg/ml) or DMF.
InChi Key FAFRRYBYQKPKSY-KBIMZEDXSA-N
Smiles ClC1=CC([C@H](O)[C@@H]2NC)=CC(O[C@@](C)(CC)[C@H](C(N3CC=C[C@H]3C(N/C(C(N/C(C(O)=O)=C/C(O)=O)=O)=C(C)/CC)=O)=O)NC([C@H](C(C)=C)NC2=O)=O)=C1O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Macrocyclic heptapeptide mycotoxin.
  • Potent anti-mitotic compound that can cause cell death.
  • Microtubule assembly inhibitor. Binds selectively to dimeric tubulin, inhibiting the formation of the microtubule spindle to block cell division. Binds at a site different from the colchicine binding site and overlapping the vinblastine binding site. Inhibits tubulin-dependent GTP hydrolysis. Binds β-tubulin from higher organisms but not α-tubulin or fungal mycelial tubulin.
  • Causes lupinosis (a degenerative disorder) in livestock fed infected lupins.
Product References
  1. Interaction of phomopsin A and related compounds with purified sheep brain tubulin: E. Lacey, et al.; Biochem. Pharmacol. 36, 2133 (1987)
  2. Effect of phomopsin A on the alkylation of tubulin: R.F. Luduena, et al.; Biochem. Pharmacol. 39, 1603 (1990)
  3. Dolastatin 10, a powerful cytostatic peptide derived from a marine animal. Inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain: R. Bai, et al.; Biochem. Pharmacol. 39, 1941 (1990)
  4. Binding selectivity of rhizoxin, phomopsin A, vinblastine, and ansamitocin P-3 to fungal tubulins: differential interactions of these antimitotic agents with brain and fungal tubulins: Y. Li, et al.; BBRC 187, 722 (1992)
  5. Interaction of phomopsin A with porcine brain tubulin. Inhibition of tubulin polymerization and binding at a rhizoxin binding site: Y. Li, et al.; Biochem. Pharmacol. 43, 219 (1992)
  6. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B: E. Hamel; Pharmacol. Ther. 55, 31 (1992)
  7. Interaction of phomopsin A with normal and subtilisin-treated bovine brain tubulin: A.R. Chaudhuri & R.F. Luduena; J. Protein Chem. 16, 99 (1997)
  8. Localization of the antimitotic peptide and depsipeptide binding site on beta-tubulin: A. Mitra & D. Sept; Biochemistry 43, 13955 (2004)
  9. Structural insight into the inhibition of tubulin by vinca domain peptide ligands: A. Cormier, et al.; EMBO Rep. 9, 1101 (2008)
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