Obatoclax mesylate

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

Description:Obatoclax, also known as GX 015-070, a synthetic small-molecule inhibitor of the bcl-2 family of proteins with potential pro-apoptotic and antineoplastic activities. Obatoclax binds to members of the Bcl-2 protein family, preventing the binding of these anti-apoptotic proteins to the pro-apoptotic proteins Bax and Bak and so promoting the activation of the apoptotic pathway in Bcl-2-overexpressing cells. The Bcl-2 family of proteins (bcl-2, bcl-xl, bcl-w, and Mcl-1) are overexpressed in a wide variety of cancers, including those of the lymphatic system, breast, lung, prostate, and colon.

Price and Availability

Obatoclax mesylate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 202050Name: Obatoclax mesylateCAS#: 803712-79-0 (mesylate)Chemical Formula: C21H23N3O4SExact Mass: 317.15281Molecular Weight: 413.49002Elemental Analysis: C, 61.00; H, 5.61; N, 10.16; O, 15.48; S, 7.75

Related CAS #:803712-67-6 (free base)803712-79-0 (mesylate)

Synonym:Obatoclax; Obatoclax mesylate; GX 015-070; GX015-070; GX-015-070; GX 015070; GX015070; GX-015070; GX 05-070; GX15070MS.

IUPAC/Chemical Name:(Z)-2-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-1H-indole methanesulfonate

InChi Key:ZFKXDVMHNXPEIY-PEZBNFGJSA-N

InChi Code:InChI=1S/C20H19N3O.CH4O3S/c1-12-8-13(2)21-16(12)10-19-20(24-3)11-18(23-19)17-9-14-6-4-5-7-15(14)22-17;1-5(2,3)4/h4-11,21-22H,1-3H3;1H3,(H,2,3,4)/b19-10-;

SMILES Code:COC1=CC(C(N2)=CC3=C2C=CC=C3)=N/C1=CC4=C(C)C=C(C)N4.CS(=O)(O)=O

Technical Data

Additional Information

Related CAS#803712-67-6 (Obatoclax free base)803712-79-0(Obatoclax mesylate) 

References

1: Díaz de Greñu B, Hernández PI, Espona M, QuiñoneroD, Light ME, Torroba T, Pérez-Tomás R, Quesada R. Synthetic ProdiginineObatoclax (GX15-070) and Related Analogues: Anion Binding, TransmembraneTransport, and Cytotoxicity Properties. Chemistry. 2011 Nov 9. doi:10.1002/chem.201101547. [Epub ahead of print] PubMed PMID: 22069220.

2: Lieber J, Ellerkamp V, Wenz J, Kirchner B, Warmann SW, Fuchs J,Armeanu-Ebinger S. Apoptosis sensitizers enhance cytotoxicity inhepatoblastoma cells. Pediatr Surg Int. 2011 Oct 5. [Epub ahead ofprint] PubMed PMID: 21971946.

3: Martínez-Paniagua MA, Baritaki S, Huerta-Yepez S, Ortiz-Navarrete VF,González-Bonilla C, Bonavida B, Vega MI. Mcl-1 and YY1 inhibition andinduction of DR5 by the BH3-mimetic Obatoclax (GX15-070) contribute inthe sensitization of B-NHL cells to TRAIL apoptosis. Cell Cycle. 2011Aug 15;10(16):2792-805. Epub 2011 Aug 15. PubMed PMID: 21822052.

4: Jóna A, Khaskhely N, Buglio D, Shafer JA, Derenzini E, Bollard CM,Medeiros LJ, Illés A, Ji Y, Younes A. The histone deacetylase inhibitorentinostat (SNDX-275) induces apoptosis in Hodgkin lymphoma cells andsynergizes with Bcl-2 family inhibitors. Exp Hematol. 2011Oct;39(10):1007-1017.e1. doi: 10.1016/j.exphem.2011.07.002. Epub 2011Jul 20. PubMed PMID: 21767511; PubMed Central PMCID: PMC3177003.

5: Acoca S, Cui Q, Shore GC, Purisima EO. Molecular dynamics study ofsmall molecule inhibitors of the Bcl-2 family. Proteins. 2011Sep;79(9):2624-36. doi: 10.1002/prot.23083. Epub 2011 Jun 30. PubMedPMID: 21721047.

6: Herishanu Y, Gibellini F, Njuguna N, Hazan-Halevy I, Farooqui M, BernS, Keyvanfar K, Lee E, Wilson W, Wiestner A. Activation of CD44, areceptor for extracellular matrix components, protects chroniclymphocytic leukemia cells from spontaneous and drug induced apoptosisthrough MCL-1. Leuk Lymphoma. 2011 Sep;52(9):1758-69. Epub 2011 Jun 8.PubMed PMID: 21649540.

7: Paik PK, Rudin CM, Pietanza MC, Brown A, Rizvi NA, Takebe N, TravisW, James L, Ginsberg MS, Juergens R, Markus S, Tyson L, Subzwari S, KrisMG, Krug LM. A phase II study of obatoclax mesylate, a Bcl-2 antagonist,plus topotecan in relapsed small cell lung cancer. Lung Cancer. 2011Dec;74(3):481-5. Epub 2011 May 26. PubMed PMID: 21620511.

8: Brem EA, Thudium K, Khubchandani S, Tsai PC, Olejniczak SH, Bhat S,Riaz W, Gu J, Iqbal A, Campagna R, Knight J, Mavis C, Hoskin P, Deeb G,Gibbs JF, Fetterly G, Czuczman MS, Hernandez-Ilizaliturri FJ. Distinctcellular and therapeutic effects of obatoclax in rituximab-sensitive and-resistant lymphomas. Br J Haematol. 2011 Jun;153(5):599-611. doi:10.1111/j.1365-2141.2011.08669.x. Epub 2011 Apr 15. PubMed PMID:21492126; PubMed Central PMCID: PMC3092002.

9: Dean EJ, Cummings J, Roulston A, Berger M, Ranson M, Blackhall F,Dive C. Optimization of circulating biomarkers of obatoclax-induced celldeath in patients with small cell lung cancer. Neoplasia. 2011Apr;13(4):339-47. PubMed PMID: 21472138; PubMed Central PMCID:PMC3071082.

10: Heidari N, Hicks MA, Harada H. GX15-070 (obatoclax) overcomesglucocorticoid resistance in acute lymphoblastic leukemia throughinduction of apoptosis and autophagy. Cell Death Dis. 2010 Sep 16;1:e76.PubMed PMID: 21364679; PubMed Central PMCID: PMC3032343.