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MedKoo Cat#: 206826 | Name: Sabutoclax
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Description:

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

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.

Chemical Structure

Sabutoclax
Sabutoclax
CAS#1228108-65-3

Theoretical Analysis

MedKoo Cat#: 206826

Name: Sabutoclax

CAS#: 1228108-65-3

Chemical Formula: C42H40N2O8

Exact Mass: 700.2785

Molecular Weight: 700.79

Elemental Analysis: C, 71.98; H, 5.75; N, 4.00; O, 18.26

Price and Availability

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5mg USD 450.00 2 Weeks
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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
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 and ethanol
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Sabutoclax inhibits the Bcl-2 family proteins Bcl-xL, Bcl-2, Mcl-1, and Bfl-1 with IC50 values of 0.31, 0.32, 0.2, and 0.62 µM, respectively. It inhibits the proliferation of BP3 B cell lymphoma cells, as well as PC3 prostate and H460 lung cancer cells with IC50 values of 0.049, 0.13, and 0.56 µM, respectively).
In vitro activity:
Combining chemotherapeutic agents with sabutoclax resulted in potent synergistic antiproliferative effects. Sabutoclax blocked BCL-2, MCL-1, BCL-xL, and BFL-1, leading to activation of caspase-3/7 and caspase-9 and modulation of Bax, Bim, PUMA, and survivin expression. Sabutoclax eliminated cancer stem cells and reduced sphere formation in drug-resistant cells by inhibiting the IL-6/STAT3 signaling pathway. Reference: Cancer Lett. 2018 Jun 1;423:47-59. https://pubmed.ncbi.nlm.nih.gov/29496539/
In vivo activity:
Sabutoclax administration mediated apoptosis in castrate-resistant PCa cells of Tgfbr2(ColTKO) mice and human xenograft PCa models. Sabutoclax had little apoptotic effect on benign prostate tissue in Tgfbr2(ColTKO) and wild-type mice. Sabutoclax blocked c-Met activation. Sabutoclax synergistically sensitized PC-3 cells to the cytotoxic effects of docetaxel. Reference: Neoplasia. 2012 Jul;14(7):656-65. https://pubmed.ncbi.nlm.nih.gov/22904682/
Solvent mg/mL mM
Solubility
DMSO 100.0 142.70
Ethanol 26.0 37.10
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 700.79 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.

Recalculate based on batch purity %
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. Hu Y, Yagüe E, Zhao J, Wang L, Bai J, Yang Q, Pan T, Zhao H, Liu J, Zhang J. Sabutoclax, pan-active BCL-2 protein family antagonist, overcomes drug resistance and eliminates cancer stem cells in breast cancer. Cancer Lett. 2018 Jun 1;423:47-59. doi: 10.1016/j.canlet.2018.02.036. Epub 2018 Feb 27. PMID: 29496539. 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. doi: 10.1593/neo.13230. PMID: 23633928; PMCID: PMC3638359. 3. Correction for Dash et al., 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. 2017 May 30;114(22):E4522-E4523. doi: 10.1073/pnas.1706353114. Epub 2017 May 22. Erratum for: Proc Natl Acad Sci U S A. 2011 May 24;108(21):8785-90. PMID: 28533399; PMCID: PMC5465882. 4. 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. doi: 10.1593/neo.12640. PMID: 22904682; PMCID: PMC3421961.
In vitro protocol:
1. Hu Y, Yagüe E, Zhao J, Wang L, Bai J, Yang Q, Pan T, Zhao H, Liu J, Zhang J. Sabutoclax, pan-active BCL-2 protein family antagonist, overcomes drug resistance and eliminates cancer stem cells in breast cancer. Cancer Lett. 2018 Jun 1;423:47-59. doi: 10.1016/j.canlet.2018.02.036. Epub 2018 Feb 27. PMID: 29496539. 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. doi: 10.1593/neo.13230. PMID: 23633928; PMCID: PMC3638359.
In vivo protocol:
1. Correction for Dash et al., 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. 2017 May 30;114(22):E4522-E4523. doi: 10.1073/pnas.1706353114. Epub 2017 May 22. Erratum for: Proc Natl Acad Sci U S A. 2011 May 24;108(21):8785-90. PMID: 28533399; PMCID: PMC5465882. 2. 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. doi: 10.1593/neo.12640. PMID: 22904682; PMCID: PMC3421961.
1: Hu Y, Yagüe E, Zhao J, Wang L, Bai J, Yang Q, Pan T, Zhao H, Liu J, Zhang J. Sabutoclax, pan-active BCL-2 protein family antagonist, overcomes drug resistance and eliminates cancer stem cells in breast cancer. Cancer Lett. 2018 Jun 1;423:47-59. doi: 10.1016/j.canlet.2018.02.036. Epub 2018 Feb 27. PMID: 29496539. 2: 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. doi: 10.1593/neo.12640. PMID: 22904682; PMCID: PMC3421961. 3: 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. doi: 10.1593/neo.13230. PMID: 23633928; PMCID: PMC3638359. 4: Li C, Song Y, Li P. MCL1 regulates cell death, tumor growth and chemosensitivity to sabutoclax in ovarian adenocarcinoma. Cell Tissue Res. 2020 Mar;379(3):625-633. doi: 10.1007/s00441-019-03105-8. Epub 2019 Nov 21. PMID: 31754782. 5: Zhang Z, Liao Y, Zhao P, Chen X, Liu Y, Wu J, Zuo H. Hypoxia-based critical gene biomarkers as prognostic reporters for gastric adenocarcinoma. Environ Toxicol. 2024 Mar;39(3):1811-1821. doi: 10.1002/tox.24064. Epub 2023 Dec 10. PMID: 38073300. 6: Wei H, Harper MT. Comparison of putative BH3 mimetics AT-101, HA14-1, sabutoclax and TW-37 with ABT-737 in platelets. Platelets. 2021 Jan 2;32(1):105-112. doi: 10.1080/09537104.2020.1724276. Epub 2020 Feb 21. PMID: 32079453. 7: 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. Erratum in: Proc Natl Acad Sci U S A. 2017 May 30;114(22):E4522-E4523. doi: 10.1073/pnas.1706353114. PMID: 21555592; PMCID: PMC3102401. 8: Correction for Dash et al., 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. 2017 May 30;114(22):E4522-E4523. doi: 10.1073/pnas.1706353114. Epub 2017 May 22. Erratum for: Proc Natl Acad Sci U S A. 2011 May 24;108(21):8785-90. doi: 10.1073/pnas.1100769108. PMID: 28533399; PMCID: PMC5465882. 9: 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. doi: 10.2174/187152012803529709. PMID: 22931411; PMCID: PMC3763986. 10: Wang RX, Zheng RR, Cai H, Yang N, Chen ZX, Zhao LP, Huang YK, Li PF, Cheng H, Chen AL, Li SY, Xu L. Coordination-Driven Self-Assembly of Biomedicine to Enhance Photodynamic Therapy by Inhibiting Proteasome and Bcl-2. Adv Healthc Mater. 2023 Sep;12(24):e2300711. doi: 10.1002/adhm.202300711. Epub 2023 May 19. PMID: 37166979. 11: 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. PMID: 26556430; PMCID: PMC4590949. 12: Shi L, Hu F, Duan Y, Wu W, Dong J, Meng X, Zhu X, Liu B. Hybrid Nanospheres to Overcome Hypoxia and Intrinsic Oxidative Resistance for Enhanced Photodynamic Therapy. ACS Nano. 2020 Feb 25;14(2):2183-2190. doi: 10.1021/acsnano.9b09032. Epub 2020 Feb 11. PMID: 32023035. 13: 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. doi: 10.18632/oncotarget.3932. PMID: 26009874; PMCID: PMC4599294. 14: 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. PMID: 21780116; PMCID: PMC3228880. 15: 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. PMID: 26032425; PMCID: PMC4453003. 16: Melo G, Silva CAB, Hague A, Parkinson EK, Rivero ERC. Anticancer effects of putative and validated BH3-mimetic drugs in head and neck squamous cell carcinomas: An overview of current knowledge. Oral Oncol. 2022 Sep;132:105979. doi: 10.1016/j.oraloncology.2022.105979. Epub 2022 Jul 8. PMID: 35816876. 17: Ba Q, Wang X, Lu Y. Establishment of a prognostic model for pancreatic cancer based on mitochondrial metabolism related genes. Discov Oncol. 2024 Aug 28;15(1):376. doi: 10.1007/s12672-024-01255-y. PMID: 39196457; PMCID: PMC11358576. 18: 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. PMID: 23333150; PMCID: PMC3968867. 19: 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. PMID: 28055968; PMCID: PMC5352431. 20: 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. PMID: 21953453; PMCID: PMC3220561.