Wortmannin
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MedKoo CAT#: 406447

CAS#: 19545-26-7

Description: Wortmannin, a steroid metabolite of the fungi Penicillium funiculosum, Talaromyces (Penicillium) wortmannii, is a specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks) and Polo-Like kinase 1 (PLK1). It has an in vitro inhibitory concentration (IC50) of around 5 nM, making it a more potent inhibitor than LY294002, another commonly used PI3K inhibitor. Wortmannin has also been reported to inhibit members of the polo-like kinase family with IC50 in the same range as for PI3K.

Chemical Structure

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Wortmannin
CAS# 19545-26-7
Instruction

Theoretical Analysis

MedKoo Cat#: 406447
Name: Wortmannin
CAS#: 19545-26-7
Chemical Formula: C23H24O8
Exact Mass: 428.15
Molecular Weight: 428.430
Elemental Analysis: C, 64.48; H, 5.65; O, 29.88

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 weeks
50mg USD 1150 2 weeks
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Synonym: Wortmannin; SL2052; SL-2052; SL 2052.

IUPAC/Chemical Name: (1S,6bR,9aS,11R,11bR)-1-(methoxymethyl)-9a,11b-dimethyl-3,6,9-trioxo-3,6,6b,7,8,9,9a,10,11,11b-decahydro-1H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetate.

InChi Key: QDLHCMPXEPAAMD-QAIWCSMKSA-N

InChi Code: InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1

SMILES Code: CC(O[C@@H](C1=C2C(C3=C4C(C(O[C@H](COC)[C@]14C)=O)=CO3)=O)C[C@]5(C)C(CC[C@]52[H])=O)=O

Appearance: White to light yellow solid powder

Purity: >98% (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, not in water

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:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 428.43 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ueda K, Nakahara T, Akanuma K, Mori A, Sakamoto K, Ishii K. Differential effects of LY294002 and wortmannin on neurons and vascular endothelial cells in the rat retina. Pharmacol Rep. 2013;65(4):854-62. PubMed PMID: 24145079.

2: Quast SA, Berger A, Eberle J. ROS-dependent phosphorylation of Bax by wortmannin sensitizes melanoma cells for TRAIL-induced apoptosis. Cell Death Dis. 2013 Oct 10;4:e839. doi: 10.1038/cddis.2013.344. PubMed PMID: 24113173; PubMed Central PMCID: PMC3824654.

3: Sun D, Bhanu Prasad BA, Schuber PT Jr, Peng Z, Maxwell DS, Martin DV, Guo L, Han D, Kurihara H, Yang DJ, Gelovani JG, Powis G, Bornmann WG. Improved synthesis of 17β-hydroxy-16α-iodo-wortmannin, 17β-hydroxy-16α-iodoPX866, and the [(131)I] analogue as useful PET tracers for PI3-kinase. Bioorg Med Chem. 2013 Sep 1;21(17):5182-7. doi: 10.1016/j.bmc.2013.06.036. Epub 2013 Jun 27. PubMed PMID: 23859776.

4: Masunaga S, Sakurai Y, Tanaka H, Suzuki M, Kondo N, Narabayashi M, Maruhashi A, Ono K. Wortmannin efficiently suppresses the recovery from radiation-induced damage in pimonidazole-unlabeled quiescent tumor cell population. J Radiat Res. 2013 Mar 1;54(2):221-9. doi: 10.1093/jrr/rrs094. Epub 2012 Oct 24. PubMed PMID: 23097299; PubMed Central PMCID: PMC3589932.

5: Yun J, Lv YG, Yao Q, Wang L, Li YP, Yi J. Wortmannin inhibits proliferation and induces apoptosis of MCF-7 breast cancer cells. Eur J Gynaecol Oncol. 2012;33(4):367-9. PubMed PMID: 23091892.

6: MacKay KB, Lowenson JD, Clarke SG. Wortmannin reduces insulin signaling and death in seizure-prone Pcmt1-/- mice. PLoS One. 2012;7(10):e46719. doi: 10.1371/journal.pone.0046719. Epub 2012 Oct 5. PubMed PMID: 23071621; PubMed Central PMCID: PMC3465263.

7: Wiedemann S, Wessela T, Schwarz K, Joachim D, Jercke M, Strasser RH, Ebner B, Simonis G. Inhibition of anti-apoptotic signals by Wortmannin induces apoptosis in the remote myocardium after LAD ligation: evidence for a protein kinase C-δ-dependent pathway. Mol Cell Biochem. 2013 Jan;372(1-2):275-83. doi: 10.1007/s11010-012-1469-6. Epub 2012 Sep 27. PubMed PMID: 23010893.

8: Li J, Li F, Wang H, Wang X, Jiang Y, Li D. Wortmannin reduces metastasis and angiogenesis of human breast cancer cells via nuclear factor-κB-dependent matrix metalloproteinase-9 and interleukin-8 pathways. J Int Med Res. 2012;40(3):867-76. Erratum in: J Int Med Res. 2012;40(4):1627. Li, J [corrected to Li, Jianguo]; Li, F [corrected to Li, Funian]; Wang, H [corrected to Wang, Haibo]; Wang, X [corrected to Wang, Xingang]; Jiang, Y [corrected to Jiang, Yao]; Li, D [corrected to Li, Dongxiao]. PubMed PMID: 22906259.

9: Karve S, Werner ME, Sukumar R, Cummings ND, Copp JA, Wang EC, Li C, Sethi M, Chen RC, Pacold ME, Wang AZ. Revival of the abandoned therapeutic wortmannin by nanoparticle drug delivery. Proc Natl Acad Sci U S A. 2012 May 22;109(21):8230-5. doi: 10.1073/pnas.1120508109. Epub 2012 Apr 30. PubMed PMID: 22547809; PubMed Central PMCID: PMC3361429.

10: Takáč T, Pechan T, Samajová O, Ovečka M, Richter H, Eck C, Niehaus K, Samaj J. Wortmannin treatment induces changes in Arabidopsis root proteome and post-Golgi compartments. J Proteome Res. 2012 Jun 1;11(6):3127-42. doi: 10.1021/pr201111n. Epub 2012 May 10. PubMed PMID: 22524784.

11: Tsai KD, Chang WW, Lin CC, Hsu SC, Lee YJ, Chen W, Shieh JC, Lin TH. Differential effects of LY294002 and wortmannin on inducible nitric oxide synthase expression in glomerular mesangial cells. Int Immunopharmacol. 2012 Mar;12(3):471-80. doi: 10.1016/j.intimp.2011.12.017. Epub 2012 Jan 9. PubMed PMID: 22240122.

12: Akter R, Hossain MZ, Kleve MG, Gealt MA. Wortmannin induces MCF-7 breast cancer cell death via the apoptotic pathway, involving chromatin condensation, generation of reactive oxygen species, and membrane blebbing. Breast Cancer (Dove Med Press). 2012 Jul 13;4:103-13. doi: 10.2147/BCTT.S31712. eCollection 2012. PubMed PMID: 24367198; PubMed Central PMCID: PMC3846925.

13: Kim SH, Jang YW, Hwang P, Kim HJ, Han GY, Kim CW. The reno-protective effect of a phosphoinositide 3-kinase inhibitor wortmannin on streptozotocin-induced proteinuric renal disease rats. Exp Mol Med. 2012 Jan 31;44(1):45-51. doi: 10.3858/emm.2012.44.1.004. PubMed PMID: 22056625; PubMed Central PMCID: PMC3277897.

14: Isosaki M, Nakayama H, Kyotani Y, Zhao J, Tomita S, Satoh H, Yoshizumi M. Prevention of the wortmannin-induced inhibition of phosphoinositide 3-kinase by sulfhydryl reducing agents. Pharmacol Rep. 2011;63(3):733-9. PubMed PMID: 21857084.

15: Cooper KG, Winfree S, Malik-Kale P, Jolly C, Ireland R, Knodler LA, Steele-Mortimer O. Activation of Akt by the bacterial inositol phosphatase, SopB, is wortmannin insensitive. PLoS One. 2011;6(7):e22260. doi: 10.1371/journal.pone.0022260. Epub 2011 Jul 14. PubMed PMID: 21779406; PubMed Central PMCID: PMC3136525.

16: Ayral-Kaloustian S, Gu J, Lucas J, Cinque M, Gaydos C, Zask A, Chaudhary I, Wang J, Di L, Young M, Ruppen M, Mansour TS, Gibbons JJ, Yu K. Hybrid inhibitors of phosphatidylinositol 3-kinase (PI3K) and the mammalian target of rapamycin (mTOR): design, synthesis, and superior antitumor activity of novel wortmannin-rapamycin conjugates. J Med Chem. 2010 Jan 14;53(1):452-9. doi: 10.1021/jm901427g. PubMed PMID: 19928864.

17: Smith RA, Yuan H, Weissleder R, Cantley LC, Josephson L. A wortmannin-cetuximab as a double drug. Bioconjug Chem. 2009 Nov;20(11):2185-9. doi: 10.1021/bc900176a. PubMed PMID: 19883074; PubMed Central PMCID: PMC3386608.

18: Hao S, Ross-Inta CM, Gietzen DW. The sensing of essential amino acid deficiency in the anterior piriform cortex, that requires the uncharged tRNA/GCN2 pathway, is sensitive to wortmannin but not rapamycin. Pharmacol Biochem Behav. 2010 Jan;94(3):333-40. doi: 10.1016/j.pbb.2009.09.014. Epub 2009 Oct 1. PubMed PMID: 19800362; PubMed Central PMCID: PMC3667674.

19: Qiong Z, Ruofan H, Xiaohua L, Xinli Z, Jingwei J, Zhaohui C. Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells. Mol Biol Rep. 2010 Jun;37(5):2397-402. doi: 10.1007/s11033-009-9748-3. Epub 2009 Sep 11. PubMed PMID: 19757185.

20: Wu Q, Chen Y, Cui G, Cheng Y. Wortmannin inhibits K562 leukemic cells by regulating PI3k/Akt channel in vitro. J Huazhong Univ Sci Technolog Med Sci. 2009 Aug;29(4):451-6. doi: 10.1007/s11596-009-0412-x. Epub 2009 Aug 7. PubMed PMID: 19662361