Luminespib mesylate anhydrous | CAS#1051919-21-1

MedKoo Cat#: 527988 | Name: Luminespib mesylate anhydrous

Description:

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

Luminespib, also known as AUY-922, NVP-AUY922, VER52296, is a derivative of 4,5-diarylisoxazole and a third-generation heat shock protein 90 (Hsp90) inhibitor with potential antineoplastic activity. Hsp90 inhibitor AUY922 has been shown to bind with high affinity to and inhibit Hsp90, resulting in the proteasomal degradation of oncogenic client proteins; the inhibition of cell proliferation; and the elevation of heat shock protein 72 (Hsp72) in a wide range of human tumor cell lines.

Chemical Structure

Luminespib mesylate anhydrous

CAS#1051919-21-1 (mesylate)

Theoretical Analysis

MedKoo Cat#: 527988

Name: Luminespib mesylate anhydrous

CAS#: 1051919-21-1 (mesylate)

Chemical Formula: C27H35N3O8S

Exact Mass: 0.0000

Molecular Weight: 561.65

Elemental Analysis: C, 57.74; H, 6.28; N, 7.48; O, 22.79; S, 5.71

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 #

747412-49-3 747412-64-2 (HCl) 1051919-26-6 (mesylate hydrate) 1051919-21-1 (mesylate)

Synonym

Luminespib mesylate anhydrous; AUY922; AUY-922; AUY 922; NVP AUY922; NVP AUY-922; VER52296 ; VER-52296 ; VER 52296

IUPAC/Chemical Name

3-Isoxazolecarboxamide, 5-(2,4-dihydroxy-5-(1-methylethyl)phenyl)-N-ethyl-4-(4-(4-morpholinylmethyl)phenyl)-, methanesulfonate (1:1)

InChi Key

ZMAQNODASNQSRR-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H31N3O5.CH4O3S/c1-4-27-26(32)24-23(18-7-5-17(6-8-18)15-29-9-11-33-12-10-29)25(34-28-24)20-13-19(16(2)3)21(30)14-22(20)31;1-5(2,3)4/h5-8,13-14,16,30-31H,4,9-12,15H2,1-3H3,(H,27,32);1H3,(H,2,3,4)

SMILES Code

O=C(C1=NOC(C2=CC(C(C)C)=C(O)C=C2O)=C1C3=CC=C(CN4CCOCC4)C=C3)NCC.CS(=O)(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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 561.65 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.

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: Gaykema SB, SchrÃ¶der CP, Vitfell-Rasmussen J, Chua S, Oude Munnink TH, Brouwers AH, Bongaerts AH, Akimov M, Fernandez-Ibarra C, Lub-de Hooge MN, de Vries EG, Swanton C, Banerji U. 89Zr-trastuzumab and 89Zr-bevacizumab PET to Evaluate the Effect of the HSP90 Inhibitor NVP-AUY922 in Metastatic Breast Cancer Patients. Clin Cancer Res. 2014 Aug 1;20(15):3945-54. doi: 10.1158/1078-0432.CCR-14-0491. PubMed PMID: 25085789. 2: Doi T, Onozawa Y, Fuse N, Yoshino T, Yamazaki K, Watanabe J, Akimov M, Robson M, Boku N, Ohtsu A. Phase I dose-escalation study of the HSP90 inhibitor AUY922 in Japanese patients with advanced solid tumors. Cancer Chemother Pharmacol. 2014 Sep;74(3):629-36. doi: 10.1007/s00280-014-2521-x. Epub 2014 Jul 25. PubMed PMID: 25059319; PubMed Central PMCID: PMC4143601. 3: Chiang NJ, Wu SN, Kao CA, Huang YM, Chen LT. Stimulation of Electroporation-Induced Inward Currents in Glioblastoma Cell Lines by the Heat Shock Protein Inhibitor AUY922. Clin Exp Pharmacol Physiol. 2014 Jun 7. doi: 10.1111/1440-1681.12273. [Epub ahead of print] PubMed PMID: 24909268. 4: Huang J, Sun C, Zhang T, Pan L, Wang S, He Q, Li D. Potent antitumor activity of HSP90 inhibitor AUY922 in adrenocortical carcinoma. Tumour Biol. 2014 May 22. [Epub ahead of print] PubMed PMID: 24850175. 5: Chen SM, Guo CL, Shi JJ, Xu YC, Chen Y, Shen YY, Su Y, Ding J, Meng LH. HSP90 inhibitor AUY922 abrogates up-regulation of RTKs by mTOR inhibitor AZD8055 and potentiates its antiproliferative activity in human breast cancer. Int J Cancer. 2014 Apr 7. doi: 10.1002/ijc.28880. [Epub ahead of print] PubMed PMID: 24706460. 6: Zitzmann K, Ailer G, Vlotides G, Spoettl G, Maurer J, GÃ¶ke B, Beuschlein F, Auernhammer CJ. Potent antitumor activity of the novel HSP90 inhibitors AUY922 and HSP990 in neuroendocrine carcinoid cells. Int J Oncol. 2013 Dec;43(6):1824-32. doi: 10.3892/ijo.2013.2130. Epub 2013 Oct 4. PubMed PMID: 24100469; PubMed Central PMCID: PMC3834873. 7: Voruganti S, Lacroix JC, Rogers CN, Rogers J, Matts RL, Hartson SD. The anticancer drug AUY922 generates a proteomics fingerprint that is highly conserved among structurally diverse Hsp90 inhibitors. J Proteome Res. 2013 Aug 2;12(8):3697-706. doi: 10.1021/pr400321x. Epub 2013 Jun 27. PubMed PMID: 23763277; PubMed Central PMCID: PMC3784992. 8: Sessa C, Shapiro GI, Bhalla KN, Britten C, Jacks KS, Mita M, Papadimitrakopoulou V, Pluard T, Samuel TA, Akimov M, Quadt C, Fernandez-Ibarra C, Lu H, Bailey S, Chica S, Banerji U. First-in-human phase I dose-escalation study of the HSP90 inhibitor AUY922 in patients with advanced solid tumors. Clin Cancer Res. 2013 Jul 1;19(13):3671-80. doi: 10.1158/1078-0432.CCR-12-3404. Epub 2013 Jun 11. PubMed PMID: 23757357. 9: Garon EB, Finn RS, Hamidi H, Dering J, Pitts S, Kamranpour N, Desai AJ, Hosmer W, Ide S, Avsar E, Jensen MR, Quadt C, Liu M, Dubinett SM, Slamon DJ. The HSP90 inhibitor NVP-AUY922 potently inhibits non-small cell lung cancer growth. Mol Cancer Ther. 2013 Jun;12(6):890-900. doi: 10.1158/1535-7163.MCT-12-0998. Epub 2013 Mar 14. PubMed PMID: 23493311; PubMed Central PMCID: PMC3681857. 10: Wainberg ZA, Anghel A, Rogers AM, Desai AJ, Kalous O, Conklin D, Ayala R, O'Brien NA, Quadt C, Akimov M, Slamon DJ, Finn RS. Inhibition of HSP90 with AUY922 induces synergy in HER2-amplified trastuzumab-resistant breast and gastric cancer. Mol Cancer Ther. 2013 Apr;12(4):509-19. doi: 10.1158/1535-7163.MCT-12-0507. Epub 2013 Feb 8. PubMed PMID: 23395886. 11: Gandhi N, Wild AT, Chettiar ST, Aziz K, Kato Y, Gajula RP, Williams RD, Cades JA, Annadanam A, Song D, Zhang Y, Hales RK, Herman JM, Armour E, DeWeese TL, Schaeffer EM, Tran PT. Novel Hsp90 inhibitor NVP-AUY922 radiosensitizes prostate cancer cells. Cancer Biol Ther. 2013 Apr;14(4):347-56. doi: 10.4161/cbt.23626. Epub 2013 Jan 28. PubMed PMID: 23358469; PubMed Central PMCID: PMC3667875. 12: Walsby EJ, Lazenby M, Pepper CJ, Knapper S, Burnett AK. The HSP90 inhibitor NVP-AUY922-AG inhibits the PI3K and IKK signalling pathways and synergizes with cytarabine in acute myeloid leukaemia cells. Br J Haematol. 2013 Apr;161(1):57-67. doi: 10.1111/bjh.12215. Epub 2013 Jan 29. PubMed PMID: 23356405. 13: Hartmann S, GÃ¼nther N, Biehl M, Katzer A, Kuger S, Worschech E, Sukhorukov VL, Krohne G, Zimmermann H, Flentje M, Djuzenova CS. Hsp90 inhibition by NVP-AUY922 and NVP-BEP800 decreases migration and invasion of irradiated normoxic and hypoxic tumor cell lines. Cancer Lett. 2013 May 1;331(2):200-10. doi: 10.1016/j.canlet.2012.12.027. Epub 2013 Jan 20. PubMed PMID: 23340178. 14: Hsueh YS, Yen CC, Shih NY, Chiang NJ, Li CF, Chen LT. Autophagy is involved in endogenous and NVP-AUY922-induced KIT degradation in gastrointestinal stromal tumors. Autophagy. 2013 Feb 1;9(2):220-33. doi: 10.4161/auto.22802. Epub 2012 Nov 29. PubMed PMID: 23196876; PubMed Central PMCID: PMC3552885. 15: Armstrong H, Wolmarans A, Mercier R, Mai B, LaPointe P. The co-chaperone Hch1 regulates Hsp90 function differently than its homologue Aha1 and confers sensitivity to yeast to the Hsp90 inhibitor NVP-AUY922. PLoS One. 2012;7(11):e49322. doi: 10.1371/journal.pone.0049322. Epub 2012 Nov 14. PubMed PMID: 23166640; PubMed Central PMCID: PMC3498168. 16: Niewidok N, Wack LJ, Schiessl S, Stingl L, Katzer A, Polat B, Sukhorukov VL, Flentje M, Djuzenova CS. Hsp90 Inhibitors NVP-AUY922 and NVP-BEP800 May Exert a Significant Radiosensitization on Tumor Cells along with a Cell Type-Specific Cytotoxicity. Transl Oncol. 2012 Oct;5(5):356-69. Epub 2012 Oct 1. PubMed PMID: 23066444; PubMed Central PMCID: PMC3470116. 17: Bao XH, Takaoka M, Hao HF, Fukazawa T, Yamatsuji T, Sakurama K, Takigawa N, Nakajima M, Fujiwara T, Naomoto Y. Antiproliferative effect of the HSP90 inhibitor NVP-AUY922 is determined by the expression of PTEN in esophageal cancer. Oncol Rep. 2013 Jan;29(1):45-50. doi: 10.3892/or.2012.2074. Epub 2012 Oct 9. PubMed PMID: 23064324. 18: Okui T, Shimo T, Fukazawa T, Mohammad Monsur Hassan N, Honami T, Ibaragi S, Takaoka M, Naomoto Y, Sasaki A. Novel HSP90 inhibitor NVP-AUY922 enhances the anti-tumor effect of temsirolimus against oral squamous cell carcinoma. Curr Cancer Drug Targets. 2013 Mar;13(3):289-99. PubMed PMID: 23016912. 19: Moser C, Lang SA, Hackl C, Wagner C, Scheiffert E, Schlitt HJ, Geissler EK, Stoeltzing O. Targeting HSP90 by the novel inhibitor NVP-AUY922 reduces growth and angiogenesis of pancreatic cancer. Anticancer Res. 2012 Jul;32(7):2551-61. PubMed PMID: 22753713. 20: Best OG, Mulligan SP. Heat shock protein-90 inhibitor, NVP-AUY922, is effective in combination with fludarabine against chronic lymphocytic leukemia cells cultured on CD40L-stromal layer and inhibits their activated/proliferative phenotype. Leuk Lymphoma. 2012 Nov;53(11):2314-20. doi: 10.3109/10428194.2012.698278. Epub 2012 Jul 9. PubMed PMID: 22646928.