| Identification | Back Directory | [Name]
PIRONETIN | [CAS]
151519-02-7 | [Synonyms]
PIRONETIN
2H-Pyran-2-one, 5-ethyl-5,6-dihydro-6-[(2R,3S,4R,5S,7E)-2-hydroxy-4-methoxy-3,5-dimethyl-7-nonen-1-yl]-, (5R,6R)- | [Molecular Formula]
C19H32O4 | [MDL Number]
MFCD08457941 | [MOL File]
151519-02-7.mol | [Molecular Weight]
324.45 |
| Chemical Properties | Back Directory | [Melting point ]
75-77 °C | [Boiling point ]
473.1±40.0 °C(Predicted) | [density ]
0.993±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Dichloromethane: soluble; DMSO: soluble; Ethanol: soluble | [form ]
A solid | [pka]
14.28±0.20(Predicted) | [color ]
Colorless to off-white |
| Hazard Information | Back Directory | [Uses]
Pironetin is an α/β unsaturated lactone isolated from Streptomyces species. Pironetin binds to α-tubulin and is a potent inhibitor of microtubule polymerization, and has cell cycle arrest and antitumor activity[1][2]. | [Definition]
ChEBI:Pironetin is an aliphatic alcohol. | [in vivo]
Pironetin (0.78-6.25 mg/kg; intraperitoneal injection; daily; for 5 days; female CDF1-SLC mice) treatment shows a moderate antitumor effect, however, a severe weight loss is observed as a side effect[1]. | Animal Model: | Female CDF1-SLC mice (10 weeks) injected with P388 murine leukemia cells[1] | | Dosage: | 0.78 mg/kg, 1.56 mg/kg, 3.13 mg/kg, 6.25 mg/kg | | Administration: | Intraperitoneal injection; daily; for 5 days | | Result: | Showed a moderate antitumor effect.
|
| [storage]
Store at -20°C | [References]
[1] Kondoh M, et al. Cell cycle arrest and antitumor activity of pironetin and its derivatives. Cancer Lett. 1998 Apr 10;126(1):29-32. DOI:10.1016/s0304-3835(97)00528-4
[2] Yang J, et al. Pironetin reacts covalently with cysteine-316 of α-tubulin to destabilize microtubule. ] Nat Commun. 2016 Jun 30;7:12103. DOI:10.1038/ncomms12103 |
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