Cat. No.: HY-116446

Pironetin

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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.

For research use only. We do not sell to patients.

Purity: 96.79%
CAS No.: 151519-02-7
Formula: C₁₉H₃₂O₄
Molecular Weight:324.45

Storage:

Pure form -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Pironetin Chemical Structure

CAS No.: 151519-02-7

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

Microtubule^[1]

Cellular Effect

Cell Line	Type	Value	Description	References
A2780	GI₅₀	22.2 nM Compound: 1	Inhibition of tubulin alpha in human A2780 cells assessed as cell growth inhibition after 48 hrs by MTT assay Inhibition of tubulin alpha in human A2780 cells assessed as cell growth inhibition after 48 hrs by MTT assay	[PMID: 30693770]
A2780	IC₅₀	0.0029 μM Compound: Pironetin	Cytotoxicity against compound-sensitive human A2780 cells after 24 hrs by MTT assay Cytotoxicity against compound-sensitive human A2780 cells after 24 hrs by MTT assay	[PMID: 21396747]
A2780	IC₅₀	0.008 μM Compound: pironetin	Cytotoxicity against human A2780 cells after 24 hrs by MTT assay Cytotoxicity against human A2780 cells after 24 hrs by MTT assay	[PMID: 25426924]
A2780	IC₅₀	26 nM Compound: 1	Inhibition of tubulin alpha in human A2780 cells assessed as reduction in cell growth Inhibition of tubulin alpha in human A2780 cells assessed as reduction in cell growth	[PMID: 30693770]
A2780 ADR	IC₅₀	0.003 μM Compound: Pironetin	Cytotoxicity against compound-resistant human A2780AD cells after 24 hrs by MTT assay Cytotoxicity against compound-resistant human A2780AD cells after 24 hrs by MTT assay	[PMID: 21396747]
A2780 ADR	IC₅₀	0.025 μM Compound: pironetin	Cytotoxicity against human A2780AD cells after 24 hrs by MTT assay Cytotoxicity against human A2780AD cells after 24 hrs by MTT assay	[PMID: 25426924]
A549	GI₅₀	7.5 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human A549 cells assessed as reduction in growth after 4 days by HCS assay Cytotoxicity against human A549 cells assessed as reduction in growth after 4 days by HCS assay	[PMID: 31130264]
DC3F	GI₅₀	9.5 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against hamster DC-3F cells assessed as reduction in growth after 4 days by HCS assay Cytotoxicity against hamster DC-3F cells assessed as reduction in growth after 4 days by HCS assay	[PMID: 31130264]
EL4	GI₅₀	15 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against C57BL/6 mouse EL4 cells assessed as reduction in growth after 3 days Cytotoxicity against C57BL/6 mouse EL4 cells assessed as reduction in growth after 3 days	[PMID: 31130264]
HCT-15	IC₅₀	<0.015 μM Compound: Pironetin	Cytotoxicity against human HCT15 cells after 48 hrs by sulforhodamine B assay Cytotoxicity against human HCT15 cells after 48 hrs by sulforhodamine B assay	[PMID: 30601004]
HEK293	IC₅₀	0.017 μM Compound: Pironetin	Cytotoxicity against HEK293 cells assessed as inhibition of cell growth after 72 hrs by MTT assay Cytotoxicity against HEK293 cells assessed as inhibition of cell growth after 72 hrs by MTT assay	[PMID: 25240870]
HEK293	IC₅₀	0.017 μM Compound: pironetin	Cytotoxicity against human HEK293 cells after 3 days by MTT assay Cytotoxicity against human HEK293 cells after 3 days by MTT assay	[PMID: 25426924]
HeLa	GI₅₀	30 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human HeLa cells assessed as reduction in growth Cytotoxicity against human HeLa cells assessed as reduction in growth	[PMID: 31130264]
HeLa	IC₅₀	0.092 μM Compound: Pironetin	Cytotoxicity against human HeLa cells after 48 hrs by sulforhodamine B assay Cytotoxicity against human HeLa cells after 48 hrs by sulforhodamine B assay	[PMID: 30601004]
HL-60	GI₅₀	20 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human HL60 cells assessed as reduction in growth after 24 hrs by MTT assay Cytotoxicity against human HL60 cells assessed as reduction in growth after 24 hrs by MTT assay	[PMID: 31130264]
HT-29	IC₅₀	0.0064 μM Compound: Pironetin	Cytotoxicity against human HT-29 cells assessed as inhibition of cell growth after 72 hrs by MTT assay Cytotoxicity against human HT-29 cells assessed as inhibition of cell growth after 72 hrs by MTT assay	[PMID: 25240870]
HT-29	IC₅₀	0.0064 μM Compound: pironetin	Cytotoxicity against human HT-29 cells after 3 days by MTT assay Cytotoxicity against human HT-29 cells after 3 days by MTT assay	[PMID: 25426924]
K562	GI₅₀	17.3 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human K562 cells assessed as reduction in growth after 4 days by MTT assay Cytotoxicity against human K562 cells assessed as reduction in growth after 4 days by MTT assay	[PMID: 31130264]
K562/Adr	GI₅₀	16 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human K562/ADR cells assessed as reduction in growth after 4 days by MTT assay Cytotoxicity against human K562/ADR cells assessed as reduction in growth after 4 days by MTT assay	[PMID: 31130264]
MCF7	GI₅₀	5 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human MCF7 cells assessed as reduction in growth after 3 days by MTT assay Cytotoxicity against human MCF7 cells assessed as reduction in growth after 3 days by MTT assay	[PMID: 31130264]
MCF7	IC₅₀	0.006 μM Compound: Pironetin	Cytotoxicity against human MCF7 cells assessed as inhibition of cell growth after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells assessed as inhibition of cell growth after 72 hrs by MTT assay	[PMID: 25240870]
MCF7	IC₅₀	0.006 μM Compound: pironetin	Cytotoxicity against human MCF7 cells after 3 days by MTT assay Cytotoxicity against human MCF7 cells after 3 days by MTT assay	[PMID: 25426924]
MCF7	IC₅₀	0.015 μM Compound: Pironetin	Cytotoxicity against human MCF7 cells after 48 hrs by sulforhodamine B assay Cytotoxicity against human MCF7 cells after 48 hrs by sulforhodamine B assay	[PMID: 30601004]
MDA-MB-231	GI₅₀	4.6 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in growth after 4 days by HCS assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in growth after 4 days by HCS assay	[PMID: 31130264]
NCI-H69	GI₅₀	17.5 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human H69 cells assessed as reduction in growth after 7 days by MTT assay Cytotoxicity against human H69 cells assessed as reduction in growth after 7 days by MTT assay	[PMID: 31130264]
P388	GI₅₀	100 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against mouse P388 cells assessed as reduction in growth after 24 hrs by MTT assay Cytotoxicity against mouse P388 cells assessed as reduction in growth after 24 hrs by MTT assay	[PMID: 31130264]
T98G	GI₅₀	7.5 nM Compound: 1; (-)-PA-48153C	Cytotoxicity against human T98G cells assessed as reduction in growth after 4 days by MTS assay Cytotoxicity against human T98G cells assessed as reduction in growth after 4 days by MTS assay	[PMID: 31130264]

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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.

Chemical Information

CAS No. 151519-02-7
Appearance Oil
Molecular Weight 324.45
Formula C₁₉H₃₂O₄
Color Colorless to off-white
SMILES

O=C1C=C[C@H]([C@H](O1)C[C@H]([C@@H]([C@@H]([C@H](C/C=C/C)C)OC)C)O)CC
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Pure form	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : < 1 mg/mL (insoluble or slightly soluble)

View the Complete Stock Solution Preparation Table

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (270 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

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. [Content Brief]

[2]. Yang J, et al. Pironetin reacts covalently with cysteine-316 of α-tubulin to destabilize microtubule. ] Nat Commun. 2016 Jun 30;7:12103. [Content Brief]

Calculators

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Pironetin

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