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Pironetin

Names

[ CAS No. ]:
151519-02-7

[ Name ]:
Pironetin

Biological Activity

[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]:

Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[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.

Chemical & Physical Properties

[ 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

Synthetic Route

Precursor & DownStream


Related Compounds