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401600-86-0-STX140 STX140

STX140

  • CAT Number: I036741
  • CAS Number: 401600-86-0
  • Molecular Formula: C19H28N2O7S2
  • Molecular Weight: 460.56
  • Purity: 98%
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STX140 is a bis-sulfamate derivative of the endogenous steroid 2-methoxyestradiol, has shown promising anticancer potency both in vitro and in vivo, with excellent bioavailability. STX140 is efficacious in vitro and in vivo in taxane-resistant breast carcinoma cells. STX140 causes apoptosis via the intrinsic mitochondrial pathway and down-regulate survivin and XIAP expression in ovarian and prostate cancer cells.


Catalog Number I036741
CAS Number 401600-86-0
Synonyms

STX140; STX-140; STX 140; 2-Methoxyestradiol-3,17-O,O-bis(sulfamate);

Molecular Formula C19H28N2O7S2
Purity 98
Solubility Soluble in DMSO
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diyl bis(sulfamate)
InChI InChI=1S/C19H28N2O7S2/c1-19-8-7-12-13(15(19)5-6-18(19)28-30(21,24)25)4-3-11-9-17(27-29(20,22)23)16(26-2)10-14(11)12/h9-10,12-13,15,18H,3-8H2,1-2H3,(H2,20,22,23)(H2,21,24,25)/t12-,13+,15-,18-,19-/m0/s1
InChIKey AQSNIXKAKUZPSI-SSTWWWIQSA-N
SMILES C[C@@]12[C@@H](OS(=O)(N)=O)CC[C@@]1([H])[C@]3([H])CCC4=C(C=C(OC)C(OS(=O)(N)=O)=C4)[C@@]3([H])CC2
Reference

1: Andring J, Dohle W, Tu C, Potter BVL, McKenna R. 3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene (STX140) and Non-Steroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity. J Med Chem. 2019 Feb 5. doi: 10.1021/acs.jmedchem.8b01990. [Epub ahead of print] PubMed PMID: 30721041.
2: Stengel C, Newman SP, Leese MP, Thomas MP, Potter BV, Reed MJ, Purohit A, Foster PA. The In Vitro and In Vivo Activity of the Microtubule Disruptor STX140 Is Mediated by Hif-1 Alpha and CAIX Expression. Anticancer Res. 2015 Oct;35(10):5249-61. PubMed PMID: 26408684; PubMed Central PMCID: PMC4597367.
3: Caira MR, Bourne SA, Samsodien H. Thermal, X-ray Structural, and Dissolution Characteristics of Solid Forms Derived from the Anticancer Agents 2-Methoxyestradiol and 2-Methoxyestradiol-3,17-O,O-Bis-Sulfamate. J Pharm Sci. 2015 Oct;104(10):3418-25. doi: 10.1002/jps.24545. Epub 2015 Jun 12. PubMed PMID: 26073557.
4: Thomas MP, Potter BV. Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women’s Health. J Med Chem. 2015 Oct 8;58(19):7634-58. doi: 10.1021/acs.jmedchem.5b00386. Epub 2015 Jun 12. PubMed PMID: 25992880; PubMed Central PMCID: PMC5159624.
5: Meyer-Losic F, Newman SP, Day JM, Reed MJ, Kasprzyk PG, Purohit A, Foster PA. STX140, but not paclitaxel, inhibits mammary tumour initiation and progression in C3(1)/SV40 T/t-antigen transgenic mice. PLoS One. 2013 Dec 6;8(12):e80305. doi: 10.1371/journal.pone.0080305. eCollection 2013. PubMed PMID: 24324595; PubMed Central PMCID: PMC3855596.
6: Vorster CJ, Joubert AM. In vitro effects of 2-methoxyestradiol-bis-sulphamate on the non-tumorigenic MCF-12A cell line. Cell Biochem Funct. 2010 Jul;28(5):412-9. doi: 10.1002/cbf.1671. PubMed PMID: 20589734.
7: Jourdan F, Leese MP, Dohle W, Hamel E, Ferrandis E, Newman SP, Purohit A, Reed MJ, Potter BV. Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate. J Med Chem. 2010 Apr 8;53(7):2942-51. doi: 10.1021/jm9018806. PubMed PMID: 20225862.
8: Stengel C, Newman SP, Leese MP, Potter BV, Reed MJ, Purohit A. Class III beta-tubulin expression and in vitro resistance to microtubule targeting agents. Br J Cancer. 2010 Jan 19;102(2):316-24. doi: 10.1038/sj.bjc.6605489. Epub 2009 Dec 22. PubMed PMID: 20029418; PubMed Central PMCID: PMC2816659.
9: Foster PA, Ho YT, Newman SP, Leese MP, Potter BV, Reed MJ, Purohit A. STX140 and STX641 cause apoptosis via the intrinsic mitochondrial pathway and down-regulate survivin and XIAP expression in ovarian and prostate cancer cells. Anticancer Res. 2009 Oct;29(10):3751-7. PubMed PMID: 19846905.
10: Day JM, Foster PA, Tutill HJ, Newman SP, Ho YT, Leese MP, Potter BV, Reed MJ, Purohit A. BCRP expression does not result in resistance to STX140 in vivo, despite the increased expression of BCRP in A2780 cells in vitro after long-term STX140 exposure. Br J Cancer. 2009 Feb 10;100(3):476-86. doi: 10.1038/sj.bjc.6604873. Epub 2009 Jan 20. PubMed PMID: 19156141; PubMed Central PMCID: PMC2658539.
11: Tagg SL, Foster PA, Leese MP, Potter BV, Reed MJ, Purohit A, Newman SP. 2-Methoxyoestradiol-3,17-O,O-bis-sulphamate and 2-deoxy-D-glucose in combination: a potential treatment for breast and prostate cancer. Br J Cancer. 2008 Dec 2;99(11):1842-8. doi: 10.1038/sj.bjc.6604752. Epub 2008 Nov 4. PubMed PMID: 18985042; PubMed Central PMCID: PMC2600694.
12: Parsons MF, Foster PA, Chander SK, Jhalli R, Newman SP, Leese MP, Potter BV, Purohit A, Reed MJ. The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer. Br J Cancer. 2008 Nov 4;99(9):1433-41. doi: 10.1038/sj.bjc.6604707. Epub 2008 Oct 7. PubMed PMID: 18841154; PubMed Central PMCID: PMC2579677.
13: Foster PA, Stengel C, Ali T, Leese MP, Potter BV, Reed MJ, Purohit A, Newman SP. A comparison of two orally bioavailable anti-cancer agents, IRC-110160 and STX140. Anticancer Res. 2008 May-Jun;28(3A):1483-91. PubMed PMID: 18630502.
14: Foster PA, Newman SP, Leese MP, Bernetiere S, Diolez C, Camara J, Hacher B, Baronnet MM, Ali T, Potter BV, Reed MJ, Purohit A. A new micronized formulation of 2-methoxyestradiol-bis-sulfamate (STX140) is therapeutically potent against breast cancer. Anticancer Res. 2008 Mar-Apr;28(2A):577-81. PubMed PMID: 18506995.
15: Foster PA, Woo LW, Potter BV, Reed MJ, Purohit A. The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer. Endocrinology. 2008 Aug;149(8):4035-42. doi: 10.1210/en.2008-0223. Epub 2008 May 1. PubMed PMID: 18450955; PubMed Central PMCID: PMC2488239.
16: Newman SP, Foster PA, Stengel C, Day JM, Ho YT, Judde JG, Lassalle M, Prevost G, Leese MP, Potter BV, Reed MJ, Purohit A. STX140 is efficacious in vitro and in vivo in taxane-resistant breast carcinoma cells. Clin Cancer Res. 2008 Jan 15;14(2):597-606. doi: 10.1158/1078-0432.CCR-07-1717. PubMed PMID: 18223236.
17: Newman SP, Foster PA, Ho YT, Day JM, Raobaikady B, Kasprzyk PG, Leese MP, Potter BV, Reed MJ, Purohit A. The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers. Br J Cancer. 2007 Dec 17;97(12):1673-82. Epub 2007 Nov 20. PubMed PMID: 18026194; PubMed Central PMCID: PMC2360283.
18: Foster PA, Ho YT, Newman SP, Kasprzyk PG, Leese MP, Potter BV, Reed MJ, Purohit A. 2-MeOE2bisMATE and 2-EtE2bisMATE induce cell cycle arrest and apoptosis in breast cancer xenografts as shown by a novel ex vivo technique. Breast Cancer Res Treat. 2008 Sep;111(2):251-60. Epub 2007 Oct 24. PubMed PMID: 17957467.
19: Newman SP, Ireson CR, Tutill HJ, Day JM, Parsons MF, Leese MP, Potter BV, Reed MJ, Purohit A. The role of 17beta-hydroxysteroid dehydrogenases in modulating the activity of 2-methoxyestradiol in breast cancer cells. Cancer Res. 2006 Jan 1;66(1):324-30. PubMed PMID: 16397246.

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