Sabutoclax

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

MedKoo CAT#: 206826

CAS#: 1228108-65-3

Description: Sabutoclax, also known as BI-97C1, is a potent a Mcl-1 Antagonist. Sabutoclax inhibits Tumorigenesis in Transgenic Mouse and Human Xenograft Models of Prostate Cancer. Sabutoclax (BI97C1) induce mitochondrial fragmentation either upstream of or independent of apoptosis.


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Sabutoclax is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206826
Name: Sabutoclax
CAS#: 1228108-65-3
Chemical Formula: C42H40N2O8
Exact Mass: 700.2785
Molecular Weight: 700.788
Elemental Analysis: C, 71.98; H, 5.75; N, 4.00; O, 18.26


Synonym: Sabutoclax; BI-97C1; BI 97C1; BI97C1.

IUPAC/Chemical Name: (1R)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-N5,N5'-bis[(2R)-2-phenylpropyl]-[2,2'-binaphthalene]-5,5'-dicarboxamide

InChi Key: RAYNZUHYMMLQQA-ZEQRLZLVSA-N

InChi Code: InChI=1S/C42H40N2O8/c1-21-15-27-29(17-31(45)39(49)35(27)41(51)43-19-23(3)25-11-7-5-8-12-25)37(47)33(21)34-22(2)16-28-30(38(34)48)18-32(46)40(50)36(28)42(52)44-20-24(4)26-13-9-6-10-14-26/h5-18,23-24,45-50H,19-20H2,1-4H3,(H,43,51)(H,44,52)/t23-,24-/m0/s1

SMILES Code: O=C(C1=C(O)C(O)=CC2=C(O)C(C3=C(C)C=C4C(C(NC[C@@H](C5=CC=CC=C5)C)=O)=C(O)C(O)=CC4=C3O)=C(C)C=C12)NC[C@@H](C6=CC=CC=C6)C


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Jackson RS 2nd, Placzek W, Fernandez A, Ziaee S, Chu CY, Wei J, Stebbins J, Kitada S, Fritz G, Reed JC, Chung LW, Pellecchia M, Bhowmick NA. Sabutoclax, a Mcl-1 antagonist, inhibits tumorigenesis in transgenic mouse and human xenograft models of prostate cancer. Neoplasia. 2012 Jul;14(7):656-65. PubMed PMID: 22904682; PubMed Central PMCID: PMC3421961.

2: Varadarajan S, Butterworth M, Wei J, Pellecchia M, Dinsdale D, Cohen GM. Sabutoclax (BI97C1) and BI112D1, putative inhibitors of MCL-1, induce mitochondrial fragmentation either upstream of or independent of apoptosis. Neoplasia. 2013 May;15(5):568-78. PubMed PMID: 23633928; PubMed Central PMCID: PMC3638359.

3: Azab B, Dash R, Das SK, Bhutia SK, Shen XN, Quinn BA, Sarkar S, Wang XY, Hedvat M, Dmitriev IP, Curiel DT, Grant S, Dent P, Reed JC, Pellecchia M, Sarkar D, Fisher PB. Enhanced delivery of mda-7/IL-24 using a serotype chimeric adenovirus (Ad.5/3) in combination with the Apogossypol derivative BI-97C1 (Sabutoclax) improves therapeutic efficacy in low CAR colorectal cancer cells. J Cell Physiol. 2012 May;227(5):2145-53. doi: 10.1002/jcp.22947. PubMed PMID: 21780116; PubMed Central PMCID: PMC3228880.

4: Dash R, Azab B, Quinn BA, Shen X, Wang XY, Das SK, Rahmani M, Wei J, Hedvat M, Dent P, Dmitriev IP, Curiel DT, Grant S, Wu B, Stebbins JL, Pellecchia M, Reed JC, Sarkar D, Fisher PB. Apogossypol derivative BI-97C1 (Sabutoclax) targeting Mcl-1 sensitizes prostate cancer cells to mda-7/IL-24-mediated toxicity. Proc Natl Acad Sci U S A. 2011 May 24;108(21):8785-90. doi: 10.1073/pnas.1100769108. Epub 2011 May 9. PubMed PMID: 21555592; PubMed Central PMCID: PMC3102401.

5: Maji S, Samal SK, Pattanaik L, Panda S, Quinn BA, Das SK, Sarkar D, Pellecchia M, Fisher PB, Dash R. Mcl-1 is an important therapeutic target for oral squamous cell carcinomas. Oncotarget. 2015 Jun 30;6(18):16623-37. PubMed PMID: 26009874; PubMed Central PMCID: PMC4599294.

6: Quinn BA, Dash R, Sarkar S, Azab B, Bhoopathi P, Das SK, Emdad L, Wei J, Pellecchia M, Sarkar D, Fisher PB. Pancreatic Cancer Combination Therapy Using a BH3 Mimetic and a Synthetic Tetracycline. Cancer Res. 2015 Jun 1;75(11):2305-15. doi: 10.1158/0008-5472.CAN-14-3013. PubMed PMID: 26032425; PubMed Central PMCID: PMC4453003.

7: Goff DJ, Court Recart A, Sadarangani A, Chun HJ, Barrett CL, Krajewska M, Leu H, Low-Marchelli J, Ma W, Shih AY, Wei J, Zhai D, Geron I, Pu M, Bao L, Chuang R, Balaian L, Gotlib J, Minden M, Martinelli G, Rusert J, Dao KH, Shazand K, Wentworth P, Smith KM, Jamieson CA, Morris SR, Messer K, Goldstein LS, Hudson TJ, Marra M, Frazer KA, Pellecchia M, Reed JC, Jamieson CH. A Pan-BCL2 inhibitor renders bone-marrow-resident human leukemia stem cells sensitive to tyrosine kinase inhibition. Cell Stem Cell. 2013 Mar 7;12(3):316-28. doi: 10.1016/j.stem.2012.12.011. Epub 2013 Jan 17. PubMed PMID: 23333150; PubMed Central PMCID: PMC3968867.

8: Sarkar S, Pradhan A, Das SK, Emdad L, Sarkar D, Pellecchia M, Fisher PB. Novel therapy of prostate cancer employing a combination of viral-based immunotherapy and a small molecule BH3 mimetic. Oncoimmunology. 2015 Sep 4;5(3):e1078059. eCollection 2016 Mar. PubMed PMID: 27141334; PubMed Central PMCID: PMC4839355.

9: Quinn BA, Lee NA, Kegelman TP, Bhoopathi P, Emdad L, Das SK, Pellecchia M, Sarkar D, Fisher PB. The Quest for an Effective Treatment for an Intractable Cancer: Established and Novel Therapies for Pancreatic Adenocarcinoma. Adv Cancer Res. 2015;127:283-306. doi: 10.1016/bs.acr.2015.04.009. Epub 2015 May 21. Review. PubMed PMID: 26093904.

10: Hedvat M, Emdad L, Das SK, Kim K, Dasgupta S, Thomas S, Hu B, Zhu S, Dash R, Quinn BA, Oyesanya RA, Kegelman TP, Sokhi UK, Sarkar S, Erdogan E, Menezes ME, Bhoopathi P, Wang XY, Pomper MG, Wei J, Wu B, Stebbins JL, Diaz PW, Reed JC, Pellecchia M, Sarkar D, Fisher PB. Selected approaches for rational drug design and high throughput screening to identify anti-cancer molecules. Anticancer Agents Med Chem. 2012 Nov;12(9):1143-55. Review. PubMed PMID: 22931411; PubMed Central PMCID: PMC3763986.

11: Graham CD, Kaza N, Pruitt HC, Gibson LM, Klocke BJ, Shevde LA, Carroll SL, Roth KA. BH3 mimetics suppress CXCL12 expression in human malignant peripheral nerve sheath tumor cells. Oncotarget. 2017 Jan 31;8(5):8670-8678. doi: 10.18632/oncotarget.14398. PubMed PMID: 28055968; PubMed Central PMCID: PMC5352431.

12: Mishra PJ, Mishra PJ, Merlino G. Integrated Genomics Identifies miR-32/MCL-1 Pathway as a Critical Driver of Melanomagenesis: Implications for miR-Replacement and Combination Therapy. PLoS One. 2016 Nov 15;11(11):e0165102. doi: 10.1371/journal.pone.0165102. eCollection 2016. PubMed PMID: 27846237; PubMed Central PMCID: PMC5113037.

13: Vogler M. Targeting BCL2-Proteins for the Treatment of Solid Tumours. Adv Med. 2014;2014:943648. doi: 10.1155/2014/943648. Epub 2014 Aug 27. Review. PubMed PMID: 26556430; PubMed Central PMCID: PMC4590949.

14: Placzek WJ, Sturlese M, Wu B, Cellitti JF, Wei J, Pellecchia M. Identification of a novel Mcl-1 protein binding motif. J Biol Chem. 2011 Nov 18;286(46):39829-35. doi: 10.1074/jbc.M111.305326. Epub 2011 Sep 27. PubMed PMID: 21953453; PubMed Central PMCID: PMC3220561.

15: Wei J, Stebbins JL, Kitada S, Dash R, Placzek W, Rega MF, Wu B, Cellitti J, Zhai D, Yang L, Dahl R, Fisher PB, Reed JC, Pellecchia M. BI-97C1, an optically pure Apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. J Med Chem. 2010 May 27;53(10):4166-76. doi: 10.1021/jm1001265. PubMed PMID: 20443627; PubMed Central PMCID: PMC2880850.