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151519-02-7

151519-02-7 structure
151519-02-7 structure
  • Name: Pironetin
  • Chemical Name: (2R,3R)-3-ethyl-2-[(E,2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylnon-7-enyl]-2,3-dihydropyran-6-one
  • CAS Number: 151519-02-7
  • Molecular Formula: C19H32O4
  • Molecular Weight: 324.45500
  • Catalog: Signaling Pathways Cell Cycle/DNA Damage Microtubule/Tubulin
  • Create Date: 2016-10-03 17:55:27
  • Modify Date: 2024-01-11 15:48:16
  • 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].
Name (2R,3R)-3-ethyl-2-[(E,2R,3S,4R,5S)-2-hydroxy-4-methoxy-3,5-dimethylnon-7-enyl]-2,3-dihydropyran-6-one
Description 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].
Related Catalog
Target

Microtubule[1]

In Vitro Pironetin (20-100 ng/mL; 24 hours; 3Y1 cells) treatment arrests the cell cycle progression at G2/M in 3Y1 cells[1]. Pironetin (1-10000 ng/mL; 3 days; HeLa, A2780 and K-NRK cells) treatment inhibits the cell proliferation. IC50 values against these cell lines are almost 10 ng/mL[1]. Cell Cycle Analysis[1] Cell Line: 3Y1 cells Concentration: 20 ng/mL, 50 ng/mL, 100 ng/mL Incubation Time: 24 hours Result: Arrested the cell cycle progression at G2/M in3Y1 cells. Cell Proliferation Assay[1] Cell Line: HeLa, A2780 and K-NRK cells Concentration: 1 ng/mL, 10 ng/mL, 100 ng/mL, 1000 ng/mL and 10000 ng/mL Incubation Time: 3 days Result: Inhibited the cell proliferation.
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.
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.

[2]. Yang J, et al. Pironetin reacts covalently with cysteine-316 of α-tubulin to destabilize microtubule. ] Nat Commun. 2016 Jun 30;7:12103.
Density 0.993 g/cm3
Boiling Point 473.1ºC at 760 mmHg
Molecular Formula C19H32O4
Molecular Weight 324.45500
Flash Point 160.3ºC
Exact Mass 324.23000
PSA 55.76000
LogP 3.49860
Vapour Pressure 6.14E-11mmHg at 25°C
Index of Refraction 1.478

Chemsrc provides CAS#:151519-02-7 MSDS, density, melting point, boiling point, structure, formula, molecular weight, synthetic route, etc.
title: CAS No. 151519-02-7 | Chemsrc address: https://m.chemsrc.com/en/baike/1190772.html

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