| Size | Price | Stock | Qty |
|---|---|---|---|
| 500μg |
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| 1mg | |||
| Other Sizes |
| Targets |
Pironetin targets α-tubulin, covalently binding to Lys352 of the α-tubulin subunit. This covalent binding inhibits microtubule polymerization, leading to disruption of the mitotic spindle and cell cycle arrest. The compound’s binding site was determined through systematic alanine scanning. As a microtubule destabilizer, Pironetin prevents the assembly of tubulin heterodimers into microtubules, thereby blocking mitotic progression.
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| ln Vitro |
Treatment with pironetin (20–100 ng/mL; 24 hours; 3Y1 cells) stops the advancement of the cell cycle at G2/M [1]. HeLa, A2780, and K-NRK cells were treated with pironetin (1–10,000 ng/mL) for three days, which decreased cell proliferation. These cell lines have IC50 values of approximately 10 ng/mL [1].
Pironetin treatment stops cell cycle progression at G2/M in 3Y1 cells at concentrations of 20–100 ng/mL for 24 hours. It inhibits cell proliferation in HeLa, A2780, and K-NRK cells with IC50 values of approximately 10 ng/mL after 3 days of treatment. The compound shows potent cytotoxicity across multiple cancer cell lines. It binds to α-tubulin and is a potent inhibitor of microtubule polymerization. |
| ln Vivo |
Although pironetin (0.78–6.25 mg/kg; i.p.; daily; for 5 days; female CDF1–SLC mice) therapy resulted in significant weight reduction, it also had mild anticancer effects [1].
Pironetin demonstrates moderate antitumor effects in vivo. In female CDF1-SLC mice (10 weeks) injected with P388 murine leukemia cells, treatment with Pironetin at 0.78–6.25 mg/kg via intraperitoneal injection daily for 5 days resulted in moderate anti-tumor effects, though significant weight reduction was also observed. The compound’s antitumor activity is attributed to its microtubule polymerization inhibition and cell cycle arrest properties. |
| Enzyme Assay |
Specific cell-free enzyme/receptor binding assay protocols for Pironetin involve assessing its binding to α-tubulin. Covalent binding to Lys352 of α-tubulin can be confirmed using mass spectrometry or alanine scanning mutagenesis. Microtubule polymerization assays are performed using purified tubulin in the presence of Pironetin, measuring the inhibition of polymerization spectrophotometrically. Binding affinity and kinetics can be determined using surface plasmon resonance or isothermal titration calorimetry.
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| Cell Assay |
Cell Cycle Analysis[1]
Cell Types: 3Y1 Cell Tested Concentrations: 20 ng/mL, 50 ng/mL, 100 ng/mL Incubation Duration: 24 hrs (hours) Experimental Results: Prevents cell cycle progression at G2/M in 3Y1 cells. Cell proliferation assay[1] Cell Types: HeLa, A2780 and K-NRK Cell Tested Concentrations: 1 ng/mL, 10 ng/mL, 100 ng/mL, 1000 ng/mL and 10000 ng/mL Incubation Duration: 3 days Experimental Results: Inhibit cell proliferation. In vitro cell-based assays for Pironetin use various cancer cell lines including 3Y1, HeLa, A2780, and K-NRK cells. For cell cycle analysis, cells are treated with 20–100 ng/mL for 24 hours, and cell cycle distribution is analyzed by flow cytometry. For cell proliferation assays, cells are treated with 1–10,000 ng/mL for 3 days, and viability is assessed using standard assays to determine IC50 values (approximately 10 ng/mL). |
| Animal Protocol |
Animal/Disease Models: Female CDF1-SLC mice (10 weeks) were injected with P388 murine leukemia cells [1]
Doses: 0.78 mg/kg, 1.56 mg/kg, 3.13 mg/kg, 6.25 mg/kg Route of Administration: intraperitoneal (ip) injection; daily The; 5-day continuous Experimental Results: demonstrated moderate anti-tumor effects. In vivo animal studies for Pironetin use female CDF1-SLC mice (10 weeks) injected with P388 murine leukemia cells. Pironetin is administered at doses of 0.78, 1.56, 3.13, and 6.25 mg/kg via intraperitoneal injection daily for 5 consecutive days. Tumor growth inhibition, body weight changes, and survival are monitored. Moderate antitumor effects are observed, though significant weight reduction occurs at higher doses. |
| ADME/Pharmacokinetics |
Detailed pharmacokinetic properties of Pironetin are not extensively reported. The compound has a molecular formula of C19H32O4 and a molecular weight of 324.46 g/mol. It has a LogP of 3.498, a density of 0.993 g/cm³, a boiling point of 473.1°C at 760 mmHg, and a flash point of 160.3°C. It appears as a colorless to off-white ointment. The compound contains one hydrogen bond donor, four hydrogen bond acceptors, and nine rotatable bonds, with six defined stereocenters.
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| Toxicity/Toxicokinetics |
Specific toxicological data for Pironetin are limited. In in vivo studies, Pironetin treatment at 0.78–6.25 mg/kg resulted in significant weight reduction in mice. The compound is classified for research use only and is not intended for human therapeutic use. As a microtubule polymerization inhibitor that arrests the cell cycle at G2/M, potential toxicities would relate to effects on rapidly dividing normal tissues. Formal toxicological profiles are not detailed in the available sources.
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| References | |
| Additional Infomation |
Pironetin is a fatty alcohol. It has been reported that Streptomyces contains Pironetin, and relevant data is available for reference.
Pironetin (CAS 151519-02-7) is an α,β-unsaturated lactone isolated from Streptomyces species that covalently binds to α-tubulin at Lys352. It is a potent inhibitor of microtubule polymerization with cell cycle arrest at G2/M and antitumor activity. The compound demonstrates IC50 values of approximately 10 ng/mL in HeLa, A2780, and K-NRK cells. In vivo, it shows moderate antitumor effects in mouse models. No clinical trial or approved indication data are available. |
| Molecular Formula |
C19H32O4
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|---|---|
| Molecular Weight |
324.4550
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| Exact Mass |
324.23
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| CAS # |
151519-02-7
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| PubChem CID |
6438891
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| Appearance |
Colorless to off-white ointment
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| Density |
0.993 g/cm3
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| Boiling Point |
473.1ºC at 760 mmHg
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| Flash Point |
160.3ºC
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| Vapour Pressure |
6.14E-11mmHg at 25°C
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| Index of Refraction |
1.478
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| LogP |
3.498
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
23
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| Complexity |
416
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| Defined Atom Stereocenter Count |
6
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| SMILES |
O(C([H])([H])[H])[C@]([H])([C@@]([H])(C([H])([H])[H])C([H])([H])/C(/[H])=C(\[H])/C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(C([H])([H])[C@]1([H])[C@@]([H])(C([H])=C([H])C(=O)O1)C([H])([H])C([H])([H])[H])O[H]
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| InChi Key |
XIHGDBYGUWEHCV-FSEPSNHWSA-N
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| InChi Code |
InChI=1S/C19H32O4/c1-6-8-9-13(3)19(22-5)14(4)16(20)12-17-15(7-2)10-11-18(21)23-17/h6,8,10-11,13-17,19-20H,7,9,12H2,1-5H3/b8-6+/t13-,14-,15+,16+,17+,19+/m0/s1
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| 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
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0820 mL | 15.4102 mL | 30.8204 mL | |
| 5 mM | 0.6164 mL | 3.0820 mL | 6.1641 mL | |
| 10 mM | 0.3082 mL | 1.5410 mL | 3.0820 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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