Obatoclax mesylate| CAS#803712-79-0 | BCl-2 inhibitor

MedKoo Cat#: 202050 | Name: Obatoclax mesylate

Description:

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

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.

Chemical Structure

Obatoclax mesylate

CAS#803712-79-0 (mesylate)

Theoretical Analysis

MedKoo Cat#: 202050

Name: Obatoclax mesylate

CAS#: 803712-79-0 (mesylate)

Chemical Formula: C21H23N3O4S

Exact Mass: 0.0000

Molecular Weight: 413.49

Elemental Analysis: C, 61.00; H, 5.61; N, 10.16; O, 15.48; S, 7.75

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,450.00	2 Weeks
1g	USD 4,650.00	2 Weeks
2g	USD 6,950.00	2 Weeks

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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=C\C4=C(C)C=C(C)N4.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, not in water

Shelf Life

>5 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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Obatoclax Mesylate (GX15-070 Mesylate), a BH3 mimetic, is a pan-BCL-2 family proteins inhibitor with a Ki of 220 nM for BCL-2.

In vitro activity:

In a panel of human colorectal cancer cell lines, obatoclax inhibits cell proliferation, suppresses clonogenicity, and induces G₁-phase cell cycle arrest, along with cyclin D1 downregulation. Cycloheximide chase analyses further revealed an evident reduction in the half-life of cyclin D1 protein by obatoclax, confirming that obatoclax downregulates cyclin D1 through induction of cyclin D1 proteasomal degradation. Lastly, threonine 286 phosphorylation of cyclin D1, which is essential for initiating cyclin D1 proteasomal degradation, was induced by obatoclax in one cell line but not others. Reference: Int J Mol Sci. 2016 Dec 27;18(1):44. https://pubmed.ncbi.nlm.nih.gov/28035994/

In vivo activity:

Potent single agent antitumor activity of Obatoclax was observed against SCC029B cell line derived subcutaneous tumors in xenograft mouse model. This study observed a significant (p < 0.05) reduction in the mean tumor volume without a significant decrease in the weight of the animals (Supplementary Figure S3). The effect was dose dependent with maximal activity observed at the cumulative dose of 5 mg/kg (Figure 11A). Reference: Oncotarget. 2016 Aug 5;8(36):60060-60079. https://pubmed.ncbi.nlm.nih.gov/28947954/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	12.09
	DMSO	31.8	76.89
	Ethanol	2.0	4.84

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 413.49 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

Formulation protocol:

1. Or CR, Chang Y, Lin WC, Lee WC, Su HL, Cheung MW, Huang CP, Ho C, Chang CC. Obatoclax, a Pan-BCL-2 Inhibitor, Targets Cyclin D1 for Degradation to Induce Antiproliferation in Human Colorectal Carcinoma Cells. Int J Mol Sci. 2016 Dec 27;18(1):44. doi: 10.3390/ijms18010044. PMID: 28035994; PMCID: PMC5297679. 2. Nguyen M, Marcellus RC, Roulston A, Watson M, Serfass L, Murthy Madiraju SR, Goulet D, Viallet J, Bélec L, Billot X, Acoca S, Purisima E, Wiegmans A, Cluse L, Johnstone RW, Beauparlant P, Shore GC. Small molecule obatoclax (GX15-070) antagonizes MCL-1 and overcomes MCL-1-mediated resistance to apoptosis. Proc Natl Acad Sci U S A. 2007 Dec 4;104(49):19512-7. doi: 10.1073/pnas.0709443104. Epub 2007 Nov 26. PMID: 18040043; PMCID: PMC2148320. 3. Espona-Fiedler M, Manuel-Manresa P, Benítez-García C, Fontova P, Quesada R, Soto-Cerrato V, Pérez-Tomás R. Antimetastatic Properties of Prodigiosin and the BH3-Mimetic Obatoclax (GX15-070) in Melanoma. Pharmaceutics. 2022 Dec 28;15(1):97. doi: 10.3390/pharmaceutics15010097. PMID: 36678726; PMCID: PMC9862601. 4. Sulkshane P, Teni T. BH3 mimetic Obatoclax (GX15-070) mediates mitochondrial stress predominantly via MCL-1 inhibition and induces autophagy-dependent necroptosis in human oral cancer cells. Oncotarget. 2016 Aug 5;8(36):60060-60079. doi: 10.18632/oncotarget.11085. PMID: 28947954; PMCID: PMC5601122.

In vitro protocol:

In vivo protocol:

1. Espona-Fiedler M, Manuel-Manresa P, Benítez-García C, Fontova P, Quesada R, Soto-Cerrato V, Pérez-Tomás R. Antimetastatic Properties of Prodigiosin and the BH3-Mimetic Obatoclax (GX15-070) in Melanoma. Pharmaceutics. 2022 Dec 28;15(1):97. doi: 10.3390/pharmaceutics15010097. PMID: 36678726; PMCID: PMC9862601. 2. Sulkshane P, Teni T. BH3 mimetic Obatoclax (GX15-070) mediates mitochondrial stress predominantly via MCL-1 inhibition and induces autophagy-dependent necroptosis in human oral cancer cells. Oncotarget. 2016 Aug 5;8(36):60060-60079. doi: 10.18632/oncotarget.11085. PMID: 28947954; PMCID: PMC5601122.

1: Liu G, Wang M, Lv X, Guan Y, Li J, Xie J. Identification of mitochondria- related gene biomarkers associated with immune infiltration in acute myocardial infarction. iScience. 2024 Jun 14;27(7):110275. doi: 10.1016/j.isci.2024.110275. PMID: 39040073; PMCID: PMC11261152. 2: Houweling M, Giczewska A, Abdul K, Nieuwenhuis N, Küçükosmanoglu A, Pastuszak K, Buijsman RC, Wesseling P, Wedekind L, Noske D, Supernat A, Bailey D, Watts C, Wurdinger T, Westerman BA. Screening of predicted synergistic multi-target therapies in glioblastoma identifies new treatment strategies. Neurooncol Adv. 2023 Jun 13;5(1):vdad073. doi: 10.1093/noajnl/vdad073. PMID: 37455945; PMCID: PMC10347974. 3: Chen W, Chen L, Guo L, Liu N, Wu T, Cheng Y, Xu P, Li Y, Yang X, Xu R, Chen B. The signature of immune-subtype specific driving transcription factors suggest potential drugs for refractory glioblastoma. Am J Cancer Res. 2023 Apr 15;13(4):1278-1294. PMID: 37168341; PMCID: PMC10164812. 4: Wang F, Zhu L. Phenotypic plasticity promotes lymph nodes metastasis and drug resistance in lung squamous cell carcinomas. Heliyon. 2023 Mar 17;9(4):e14614. doi: 10.1016/j.heliyon.2023.e14614. PMID: 37025908; PMCID: PMC10070384. 5: Ma Q, Hui Y, Huang BR, Yang BF, Li JX, Fan TT, Gao XC, Ma DY, Chen WF, Pei ZX. Ferroptosis and cuproptosis prognostic signature for prediction of prognosis, immunotherapy and drug sensitivity in hepatocellular carcinoma: development and validation based on TCGA and ICGC databases. Transl Cancer Res. 2023 Jan 30;12(1):46-64. doi: 10.21037/tcr-22-2203. Epub 2022 Dec 19. PMID: 36760376; PMCID: PMC9906058. 6: Kuhn C, Boeschen M, Philip M, Schöneberg T, Thor D, Horn S. Candidate drugs associated with sensitivity of cancer cell lines with DLST amplification or high mRNA levels. Oncotarget. 2023 Jan 12;14:14-20. doi: 10.18632/oncotarget.28342. PMID: 36634214; PMCID: PMC9836382. 7: Chen S, Ren Y, Duan P. Biomimetic nanoparticle loading obatoclax mesylate for the treatment of non-small-cell lung cancer (NSCLC) through suppressing Bcl-2 signaling. Biomed Pharmacother. 2020 Sep;129:110371. doi: 10.1016/j.biopha.2020.110371. Epub 2020 Jun 18. PMID: 32563984. 8: Han Z, Liang J, Li Y, He J. Drugs and Clinical Approaches Targeting the Antiapoptotic Protein: A Review. Biomed Res Int. 2019 Sep 29;2019:1212369. doi: 10.1155/2019/1212369. PMID: 31662966; PMCID: PMC6791192. 9: Klein AS, Brass HUC, Klebl DP, Classen T, Loeschcke A, Drepper T, Sievers S, Jaeger KE, Pietruszka J. Preparation of Cyclic Prodiginines by Mutasynthesis in Pseudomonas putida KT2440. Chembiochem. 2018 Jul 16;19(14):1545-1552. doi: 10.1002/cbic.201800154. Epub 2018 Jun 17. PMID: 29719131. 10: Schimmer AD, Raza A, Carter TH, Claxton D, Erba H, DeAngelo DJ, Tallman MS, Goard C, Borthakur G. A multicenter phase I/II study of obatoclax mesylate administered as a 3- or 24-hour infusion in older patients with previously untreated acute myeloid leukemia. PLoS One. 2014 Oct 6;9(10):e108694. doi: 10.1371/journal.pone.0108694. PMID: 25285531; PMCID: PMC4186779. 11: Arellano ML, Borthakur G, Berger M, Luer J, Raza A. A phase II, multicenter, open-label study of obatoclax mesylate in patients with previously untreated myelodysplastic syndromes with anemia or thrombocytopenia. Clin Lymphoma Myeloma Leuk. 2014 Dec;14(6):534-9. doi: 10.1016/j.clml.2014.04.007. Epub 2014 Jun 12. PMID: 25052051. 12: Langer CJ, Albert I, Ross HJ, Kovacs P, Blakely LJ, Pajkos G, Somfay A, Zatloukal P, Kazarnowicz A, Moezi MM, Schreeder MT, Schnyder J, Ao-Baslock A, Pathak AK, Berger MS; GEM017 Investigators. Randomized phase II study of carboplatin and etoposide with or without obatoclax mesylate in extensive-stage small cell lung cancer. Lung Cancer. 2014 Sep;85(3):420-8. doi: 10.1016/j.lungcan.2014.05.003. Epub 2014 May 13. PMID: 24997137. 13: Goy A, Hernandez-Ilzaliturri FJ, Kahl B, Ford P, Protomastro E, Berger M. A phase I/II study of the pan Bcl-2 inhibitor obatoclax mesylate plus bortezomib for relapsed or refractory mantle cell lymphoma. Leuk Lymphoma. 2014 Dec;55(12):2761-8. doi: 10.3109/10428194.2014.907891. Epub 2014 May 6. PMID: 24679008; PMCID: PMC4349217. 14: Goy A, Berger M, Ford P, Feldman T, Mato A, Bejot C, Fung HC. Sequential single-agent obatoclax mesylate (GX15-070MS) followed by combination with rituximab in patients with previously untreated follicular lymphoma. Leuk Lymphoma. 2014 Dec;55(12):2932-4. doi: 10.3109/10428194.2014.900760. Epub 2014 Apr 22. PMID: 24611663. 15: Chiappori A, Williams C, Northfelt DW, Adams JW, Malik S, Edelman MJ, Rosen P, Van Echo DA, Berger MS, Haura EB. Obatoclax mesylate, a pan-bcl-2 inhibitor, in combination with docetaxel in a phase 1/2 trial in relapsed non-small-cell lung cancer. J Thorac Oncol. 2014 Jan;9(1):121-5. doi: 10.1097/JTO.0000000000000027. PMID: 24346101; PMCID: PMC4666503. 16: Goard CA, Schimmer AD. An evidence-based review of obatoclax mesylate in the treatment of hematological malignancies. Core Evid. 2013;8:15-26. doi: 10.2147/CE.S42568. Epub 2013 Mar 14. PMID: 23515850; PMCID: PMC3601645. 17: Urtishak KA, Edwards AY, Wang LS, Hudome A, Robinson BW, Barrett JS, Cao K, Cory L, Moore JS, Bantly AD, Yu QC, Chen IM, Atlas SR, Willman CL, Kundu M, Carroll AJ, Heerema NA, Devidas M, Hilden JM, Dreyer ZE, Hunger SP, Reaman GH, Felix CA. Potent obatoclax cytotoxicity and activation of triple death mode killing across infant acute lymphoblastic leukemia. Blood. 2013 Apr 4;121(14):2689-703. doi: 10.1182/blood-2012-04-425033. Epub 2013 Feb 7. PMID: 23393050; PMCID: PMC3617634. 18: Oki Y, Copeland A, Hagemeister F, Fayad LE, Fanale M, Romaguera J, Younes A. Experience with obatoclax mesylate (GX15-070), a small molecule pan-Bcl-2 family antagonist in patients with relapsed or refractory classical Hodgkin lymphoma. Blood. 2012 Mar 1;119(9):2171-2. doi: 10.1182/blood-2011-11-391037. PMID: 22383790. 19: Joudeh J, Claxton D. Obatoclax mesylate : pharmacology and potential for therapy of hematological neoplasms. Expert Opin Investig Drugs. 2012 Mar;21(3):363-73. doi: 10.1517/13543784.2012.652302. Epub 2012 Feb 11. PMID: 22324354. 20: Paik PK, Rudin CM, Pietanza MC, Brown A, Rizvi NA, Takebe N, Travis W, James L, Ginsberg MS, Juergens R, Markus S, Tyson L, Subzwari S, Kris MG, Krug LM. A phase II study of obatoclax mesylate, a Bcl-2 antagonist, plus topotecan in relapsed small cell lung cancer. Lung Cancer. 2011 Dec;74(3):481-5. doi: 10.1016/j.lungcan.2011.05.005. Epub 2011 May 26. PMID: 21620511; PMCID: PMC3715068.