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MedKoo Cat#: 207062 | Name: Minnelide free acid

Description:

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

Minnelide is an effective therapy against pancreatic cancer. Minnelide Inhibits Androgen Dependent, Castration Resistant Prostate Cancer Growth by Decreasing Expression of Androgen Receptor Full Length and Splice Variants. Minnelide reduced tumor volume in multiple models of pancreatic cancer. Minnelide was a more effective drug against pancreatic cancer models. It effectively reduced tumor burden and tumor related morbidity in different unique but complementary mouse models. It reduced metastatic spread and increased survival in the different models as well.

Chemical Structure

Minnelide free acid
Minnelide free acid
CAS#1254885-39-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 207062

Name: Minnelide free acid

CAS#: 1254885-39-6 (free acid)

Chemical Formula: C21H27O10P

Exact Mass: 470.1342

Molecular Weight: 470.41

Elemental Analysis: C, 53.62; H, 5.79; O, 34.01; P, 6.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1254885-39-6 (free acid) 1254702-87-8 (sodium)
Synonym
Minnelide free acid; 14-O-Phosphonooxymethyltriptolide;
IUPAC/Chemical Name
(((5bS,6aS,7aR,8R,8aS,9aS,9bS,10aS,10bS)-8a-isopropyl-10b-methyl-3-oxo-1,2,3,5,5b,6,6a,8,8a,9a,9b,10b-dodecahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-8-yl)oxy)methyl dihydrogen phosphate
InChi Key
O=P(O)(OCO[C@@H]([C@]1(O2)[C@]2([H])C[C@]34[H])[C@]5(C(C)C)[C@](O5)([H])[C@@]6([H])[C@@]1(O6)[C@@]3(C)CCC7=C4COC7=O)O
InChi Code
InChI=1S/C21H27O10P/c1-9(2)19-14(30-19)15-21(31-15)18(3)5-4-10-11(7-26-16(10)22)12(18)6-13-20(21,29-13)17(19)27-8-28-32(23,24)25/h9,12-15,17H,4-8H2,1-3H3,(H2,23,24,25)/t12-,13-,14-,15-,17+,18-,19-,20+,21+/m0/s1
SMILES Code
O=P(O)(OCO[C@@H]([C@]1(O2)[C@]2([H])C[C@]34[H])[C@]5(C(C)C)[C@](O5)([H])[C@@]6([H])[C@@]1(O6)[C@@]3(C)CCC7=C4COC7=O)O
Appearance
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
Shelf Life
>3 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 470.41 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: Kim ST, Kim SY, Lee J, Kim K, Park SH, Park YS, Lim HY, Kang WK, Park JO. Triptolide as a novel agent in pancreatic cancer: the validation using patient derived pancreatic tumor cell line. BMC Cancer. 2018 Nov 12;18(1):1103. doi: 10.1186/s12885-018-4995-0. PubMed PMID: 30419860; PubMed Central PMCID: PMC6233492. 2: Dauer P, Zhao X, Gupta VK, Sharma N, Kesh K, Gnamlin P, Dudeja V, Vickers SM, Banerjee S, Saluja A. Inactivation of Cancer-Associated-Fibroblasts Disrupts Oncogenic Signaling in Pancreatic Cancer Cells and Promotes Its Regression. Cancer Res. 2018 Mar 1;78(5):1321-1333. doi: 10.1158/0008-5472.CAN-17-2320. Epub 2017 Dec 19. PubMed PMID: 29259015; PubMed Central PMCID: PMC5935584. 3: McGinn O, Gupta VK, Dauer P, Arora N, Sharma N, Nomura A, Dudeja V, Saluja A, Banerjee S. Inhibition of hypoxic response decreases stemness and reduces tumorigenic signaling due to impaired assembly of HIF1 transcription complex in pancreatic cancer. Sci Rep. 2017 Aug 11;7(1):7872. doi: 10.1038/s41598-017-08447-3. PubMed PMID: 28801636; PubMed Central PMCID: PMC5554238. 4: Giri B, Sethi V, Modi S, Garg B, Banerjee S, Saluja A, Dudeja V. "Heat shock protein 70 in pancreatic diseases: Friend or foe". J Surg Oncol. 2017 Jul;116(1):114-122. doi: 10.1002/jso.24653. Epub 2017 May 22. Review. PubMed PMID: 28543919; PubMed Central PMCID: PMC5714583. 5: Khanipour Roshan S, Spano AD, McKinney AM, Nascene DR. Potentially reversible acute cerebellar toxicity associated with Minnelide. Neuroradiology. 2017 Apr;59(4):419-421. doi: 10.1007/s00234-017-1809-z. Epub 2017 Mar 16. PubMed PMID: 28303374. 6: Arora N, Alsaied O, Dauer P, Majumder K, Modi S, Giri B, Dudeja V, Banerjee S, Von Hoff D, Saluja A. Downregulation of Sp1 by Minnelide leads to decrease in HSP70 and decrease in tumor burden of gastric cancer. PLoS One. 2017 Feb 13;12(2):e0171827. doi: 10.1371/journal.pone.0171827. eCollection 2017. PubMed PMID: 28192510; PubMed Central PMCID: PMC5305197. 7: Isharwal S, Modi S, Arora N, Uhlrich C 3rd, Giri B, Barlass U, Soubra A, Chugh R, Dehm SM, Dudeja V, Saluja A, Banerjee S, Konety B. Minnelide Inhibits Androgen Dependent, Castration Resistant Prostate Cancer Growth by Decreasing Expression of Androgen Receptor Full Length and Splice Variants. Prostate. 2017 May;77(6):584-596. doi: 10.1002/pros.23298. Epub 2017 Feb 1. PubMed PMID: 28144973. 8: Nomura A, Majumder K, Giri B, Dauer P, Dudeja V, Roy S, Banerjee S, Saluja AK. Inhibition of NF-kappa B pathway leads to deregulation of epithelial-mesenchymal transition and neural invasion in pancreatic cancer. Lab Invest. 2016 Dec;96(12):1268-1278. doi: 10.1038/labinvest.2016.109. Epub 2016 Oct 24. PubMed PMID: 27775688; PubMed Central PMCID: PMC5121017. 9: Kumar A, Corey C, Scott I, Shiva S, D'Cunha J. Minnelide/Triptolide Impairs Mitochondrial Function by Regulating SIRT3 in P53-Dependent Manner in Non-Small Cell Lung Cancer. PLoS One. 2016 Aug 8;11(8):e0160783. doi: 10.1371/journal.pone.0160783. eCollection 2016. PubMed PMID: 27501149; PubMed Central PMCID: PMC4976872. 10: Nomura A, Dauer P, Gupta V, McGinn O, Arora N, Majumdar K, Uhlrich C 3rd, Dalluge J, Dudeja V, Saluja A, Banerjee S. Microenvironment mediated alterations to metabolic pathways confer increased chemo-resistance in CD133+ tumor initiating cells. Oncotarget. 2016 Aug 30;7(35):56324-56337. doi: 10.18632/oncotarget.10838. PubMed PMID: 27472388; PubMed Central PMCID: PMC5302917. 11: Saluja AK, Dudeja V, Banerjee S. Evolution of novel therapeutic options for pancreatic cancer. Curr Opin Gastroenterol. 2016 Jul 21. [Epub ahead of print] PubMed PMID: 27454027. 12: Nomura A, McGinn O, Dudeja V, Sangwan V, Saluja AK, Banerjee S. Minnelide effectively eliminates CD133(+) side population in pancreatic cancer. Mol Cancer. 2015 Nov 23;14:200. doi: 10.1186/s12943-015-0470-6. PubMed PMID: 26597727; PubMed Central PMCID: PMC4657383. 13: Patil S, Lis LG, Schumacher RJ, Norris BJ, Morgan ML, Cuellar RA, Blazar BR, Suryanarayanan R, Gurvich VJ, Georg GI. Phosphonooxymethyl Prodrug of Triptolide: Synthesis, Physicochemical Characterization, and Efficacy in Human Colon Adenocarcinoma and Ovarian Cancer Xenografts. J Med Chem. 2015 Dec 10;58(23):9334-44. doi: 10.1021/acs.jmedchem.5b01329. Epub 2015 Nov 24. PubMed PMID: 26596892; PubMed Central PMCID: PMC4678411. 14: Majumder K, Arora N, Modi S, Chugh R, Nomura A, Giri B, Dawra R, Ramakrishnan S, Banerjee S, Saluja A, Dudeja V. A Novel Immunocompetent Mouse Model of Pancreatic Cancer with Robust Stroma: a Valuable Tool for Preclinical Evaluation of New Therapies. J Gastrointest Surg. 2016 Jan;20(1):53-65; discussion 65. doi: 10.1007/s11605-015-2985-y. Epub 2015 Nov 18. PubMed PMID: 26582596; PubMed Central PMCID: PMC5724755. 15: Modi S, Kir D, Giri B, Majumder K, Arora N, Dudeja V, Banerjee S, Saluja AK. Minnelide Overcomes Oxaliplatin Resistance by Downregulating the DNA Repair Pathway in Pancreatic Cancer. J Gastrointest Surg. 2016 Jan;20(1):13-23; discussion 23-4. doi: 10.1007/s11605-015-3000-3. Epub 2015 Oct 26. PubMed PMID: 26503259; PubMed Central PMCID: PMC4698020. 16: Brincks EL, Kucaba TA, James BR, Murphy KA, Schwertfeger KL, Sangwan V, Banerjee S, Saluja AK, Griffith TS. Triptolide enhances the tumoricidal activity of TRAIL against renal cell carcinoma. FEBS J. 2015 Dec;282(24):4747-4765. doi: 10.1111/febs.13532. Epub 2015 Oct 18. PubMed PMID: 26426449; PubMed Central PMCID: PMC4715782. 17: Banerjee S, Modi S, McGinn O, Zhao X, Dudeja V, Ramakrishnan S, Saluja AK. Impaired Synthesis of Stromal Components in Response to Minnelide Improves Vascular Function, Drug Delivery, and Survival in Pancreatic Cancer. Clin Cancer Res. 2016 Jan 15;22(2):415-25. doi: 10.1158/1078-0432.CCR-15-1155. Epub 2015 Sep 24. PubMed PMID: 26405195; PubMed Central PMCID: PMC4716007. 18: Ganguly S, Home T, Yacoub A, Kambhampati S, Shi H, Dandawate P, Padhye S, Saluja AK, McGuirk J, Rao R. Targeting HSF1 disrupts HSP90 chaperone function in chronic lymphocytic leukemia. Oncotarget. 2015 Oct 13;6(31):31767-79. doi: 10.18632/oncotarget.5167. PubMed PMID: 26397138; PubMed Central PMCID: PMC4741638. 19: Banerjee S, Saluja A. Minnelide, a novel drug for pancreatic and liver cancer. Pancreatology. 2015 Jul;15(4 Suppl):S39-43. doi: 10.1016/j.pan.2015.05.472. Epub 2015 Jun 18. Review. PubMed PMID: 26122306; PubMed Central PMCID: PMC4515388. 20: Jacobson BA, Chen EZ, Tang S, Belgum HS, McCauley JA, Evenson KA, Etchison RG, Jay-Dixon J, Patel MR, Raza A, Saluja AK, D'Cunha J, Kratzke RA. Triptolide and its prodrug minnelide suppress Hsp70 and inhibit in vivo growth in a xenograft model of mesothelioma. Genes Cancer. 2015 Mar;6(3-4):144-52. PubMed PMID: 26000097; PubMed Central PMCID: PMC4426951.

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