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MedKoo Cat#: 561750 | Name: Pironetin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pironetin is a natural α-tubulin-binding agent with potent antiproliferative activity. It acts by inhibiting cell division by forming a covalent adduct with α-tubulin. Pironetin is a binding site for microtubule destabilizing agents on tubulin.

Chemical Structure

Pironetin
Pironetin
CAS#151519-02-7

Theoretical Analysis

MedKoo Cat#: 561750

Name: Pironetin

CAS#: 151519-02-7

Chemical Formula: C19H32O4

Exact Mass: 324.2301

Molecular Weight: 324.46

Elemental Analysis: C, 70.33; H, 9.94; O, 19.72

Price and Availability

Size Price Availability Quantity
1mg USD 385.00
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Related CAS #
No Data
Synonym
(–)-Pironetin, NK 10958, NL 9C, PA 48153c, Pironetin
IUPAC/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
InChi Key
XIHGDBYGUWEHCV-FSEPSNHWSA-N
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
SMILES Code
O=C1C=C[C@@H](CC)[C@@H](C[C@@H](O)[C@H](C)[C@H](OC)[C@@H](C)C/C=C/C)O1
Appearance
Solid powder
Purity
>70% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 324.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Huang DS, Wong HL, Georg GI. Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. Bioorg Med Chem Lett. 2017 Nov 11. pii: S0960-894X(17)31059-4. doi: 10.1016/j.bmcl.2017.10.057. [Epub ahead of print] PubMed PMID: 29138028. 2: Huang DS, Wong HL, Georg GI. Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin. ChemMedChem. 2017 Apr 6;12(7):520-528. doi: 10.1002/cmdc.201700084. Epub 2017 Mar 22. PubMed PMID: 28261964; PubMed Central PMCID: PMC5413833. 3: Roldán S, Cardona A, Conesa L, Murga J, Falomir E, Carda M, Marco JA. Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring. Org Biomol Chem. 2016 Dec 20;15(1):220-232. PubMed PMID: 27901163. 4: Prota AE, Setter J, Waight AB, Bargsten K, Murga J, Diaz JF, Steinmetz MO. Pironetin Binds Covalently to αCys316 and Perturbs a Major Loop and Helix of α-Tubulin to Inhibit Microtubule Formation. J Mol Biol. 2016 Jul 31;428(15):2981-8. doi: 10.1016/j.jmb.2016.06.023. Epub 2016 Jul 6. PubMed PMID: 27395016. 5: Yang J, Wang Y, Wang T, Jiang J, Botting CH, Liu H, Chen Q, Yang J, Naismith JH, Zhu X, Chen L. Pironetin reacts covalently with cysteine-316 of α-tubulin to destabilize microtubule. Nat Commun. 2016 Jun 30;7:12103. doi: 10.1038/ncomms12103. PubMed PMID: 27357539; PubMed Central PMCID: PMC4931326. 6: Vilanova C, Díaz-Oltra S, Murga J, Falomir E, Carda M, Marco JA. Inhibitory effect of pironetin analogue/colchicine hybrids on the expression of the VEGF, hTERT and c-Myc genes. Bioorg Med Chem Lett. 2015 Aug 15;25(16):3194-8. doi: 10.1016/j.bmcl.2015.05.092. Epub 2015 Jun 5. PubMed PMID: 26094121. 7: Torijano-Gutiérrez S, Vilanova C, Díaz-Oltra S, Murga J, Falomir E, Carda M, Redondo-Horcajo M, Díaz JF, Barasoain I, Marco JA. The Mechanism of the Interactions of Pironetin Analog/Combretastatin A-4 Hybrids with Tubulin. Arch Pharm (Weinheim). 2015 Aug;348(8):541-7. doi: 10.1002/ardp.201500106. Epub 2015 Jun 17. PubMed PMID: 26085125. 8: Vilanova C, Díaz-Oltra S, Murga J, Falomir E, Carda M, Redondo-Horcajo M, Díaz JF, Barasoain I, Marco JA. Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. J Med Chem. 2014 Dec 26;57(24):10391-403. doi: 10.1021/jm501112q. Epub 2014 Dec 12. PubMed PMID: 25426924. 9: Vilanova C, Torijano-Gutiérrez S, Díaz-Oltra S, Murga J, Falomir E, Carda M, Alberto Marco J. Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. Eur J Med Chem. 2014 Nov 24;87:125-30. doi: 10.1016/j.ejmech.2014.09.053. Epub 2014 Sep 16. PubMed PMID: 25240870. 10: Bañuelos-Hernández AE, Mendoza-Espinoza JA, Pereda-Miranda R, Cerda-García-Rojas CM. Studies of (-)-pironetin binding to α-tubulin: conformation, docking, and molecular dynamics. J Org Chem. 2014 May 2;79(9):3752-64. doi: 10.1021/jo500420j. Epub 2014 Apr 24. PubMed PMID: 24761989. 11: Paños J, Díaz-Oltra S, Sánchez-Peris M, García-Pla J, Murga J, Falomir E, Carda M, Redondo-Horcajo M, Díaz JF, Barasoain I, Marco JA. Synthesis and biological evaluation of truncated α-tubulin-binding pironetin analogues lacking alkyl pendants in the side chain or the dihydropyrone ring. Org Biomol Chem. 2013 Sep 21;11(35):5809-26. doi: 10.1039/c3ob40854j. PubMed PMID: 23892508. 12: Marco JA, García-Pla J, Carda M, Murga J, Falomir E, Trigili C, Notararigo S, Díaz JF, Barasoain I. Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. Eur J Med Chem. 2011 May;46(5):1630-7. doi: 10.1016/j.ejmech.2011.02.011. Epub 2011 Feb 22. PubMed PMID: 21396747. 13: Nising CF, Hillebrand S, Rodefeld L. Recent developments in the total synthesis of fungicidal natural products--a crop protection perspective. Chem Commun (Camb). 2011 Apr 14;47(14):4062-73. doi: 10.1039/c0cc05178k. Epub 2011 Feb 1. Review. PubMed PMID: 21286632. 14: Vogt A, McPherson PA, Shen X, Balachandran R, Zhu G, Raccor BS, Nelson SG, Tsang M, Day BW. High-content analysis of cancer-cell-specific apoptosis and inhibition of in vivo angiogenesis by synthetic (-)-pironetin and analogs. Chem Biol Drug Des. 2009 Oct;74(4):358-68. doi: 10.1111/j.1747-0285.2009.00866.x. Epub 2009 Aug 18. PubMed PMID: 19691472; PubMed Central PMCID: PMC2963022. 15: Crimmins MT, Dechert AM. Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones. Org Lett. 2009 Apr 2;11(7):1635-8. doi: 10.1021/ol9003228. PubMed PMID: 19281219; PubMed Central PMCID: PMC2701212. 16: Bressy C, Vors JP, Hillebrand S, Arseniyadis S, Cossy J. Asymmetric total synthesis of the immunosuppressant (-)-pironetin. Angew Chem Int Ed Engl. 2008;47(52):10137-40. doi: 10.1002/anie.200802423. PubMed PMID: 19025743. 17: Tamura Y, Simizu S, Muroi M, Takagi S, Kawatani M, Watanabe N, Osada H. Polo-like kinase 1 phosphorylates and regulates Bcl-x(L) during pironetin-induced apoptosis. Oncogene. 2009 Jan 8;28(1):107-16. doi: 10.1038/onc.2008.368. Epub 2008 Sep 29. PubMed PMID: 18820703. 18: Yoshida M, Matsui Y, Ikarashi Y, Usui T, Osada H, Wakasugi H. Antiproliferating activity of the mitotic inhibitor pironetin against vindesine- and paclitaxel-resistant human small cell lung cancer H69 cells. Anticancer Res. 2007 Mar-Apr;27(2):729-36. PubMed PMID: 17465195. 19: Enders D, Dhulut S, Steinbusch D, Herrbach A. Asymmetric total synthesis of (-)-pironetin employing the SAMP/RAMP hydrazone methodology. Chemistry. 2007;13(14):3942-9. PubMed PMID: 17295364. 20: Alpízar-Pedraza D, Veulens AN, Ginarte YMÁ, Piloto-Ferrer J, Sánchez-Lamar Á. Xanthatin and 8-epi-xanthatin as new potential colchicine binding site inhibitors: a computational study. J Mol Model. 2023 Jan 11;29(2):36. doi: 10.1007/s00894-022-05428-w. PMID: 36627468.