957135-43-2|SM-164|(3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-((1,4-phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide)|-范德生物科技公司

SM-164

NMR下载 COA and HPLC MSDS下载
names：
(3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-((1,4-phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide)
CAS号：
957135-43-2
MDL Number：
MF(分子式)： C62H84N14O6 MW(分子量)： 1121.45
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文别名	(3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-((1,4-phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide)
英文别名	SM 164; SM164; SM-164.
CAS号	957135-43-2
Inchi	InChI=1S/C62H84N14O6/c1-41(63-3)57(77)65-49-27-13-11-25-47-33-35-53(75(47)61(49)81)59(79)67-55(45-21-7-5-8-22-45)51-39-73(71-69-51)37-17-15-19-43-29-31-44(32-30-43)20-16-18-38-74-40-52(70-72-74)56(46-23-9-6-10-24-46)68-60(80)54-36-34-48-26-12-14-28-50(62(82)76(48)54)66-58(78)42(2)64-4/h5-10,21-24,29-32,39-42,47-50,53-56,63-64H,11-20,25-28,33-38H2,1-4H3,(H,65,77)(H,66,78)(H,67,79)(H,68,80)/t41-,42-,47-,48-,49-,50-,53-,54-,55-,56-/m0/s1
InchiKey	LGYDZXNSSLRFJS-IOQQVAQYSA-N
分子式 Formula	C62H84N14O6
分子量 Molecular Weight	1121.45
溶解度Solubility
性状	Solid powder
储藏条件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

产品说明	SM-164(CAS:957135-43-2):仅限应用于工业或者科学研究过程中非医疗目的，不应用于人类或动物的临床诊断以及治过程疗，该产品非药用，非食用。
Introduction	SM-164 is a potent cell-permeable and bivalent Smac mimetic which bind to a XIAP protein and binds to cIAP-1 and cIAP-2 proteins. It is developed as an anticancer agent. It plays its antitumor roles through inducing degradation of cellular inhibitor of apoptosis protein (cIAP)-1/2, antagonizing X-linked inhibitor of apoptosis protein (XIAP) and inducing TNFα–dependent apoptosis in tumor cells. SM-164 is a bivalent mimetic containing two SM-122 analogues. It binds to cIAP-1 protein containing bothBIR2 and BIR3 domains, cIAP-2 BIR3 protein and XIAP protein containing both BIR2 and BIR3 domains.
Application1
Application2
Application3

警示图
危险性	Warning
危险性警示
安全声明
安全防护
备注

[1]Kocab AJ, Veloso A, Paulsen MT, Ljungman M, Duckett CS. Effects of physiological and synthetic IAP antagonism on c-IAP-dependent signaling. Oncogene. 2015 Oct;34(43):5472-8[1]doi: 10.1038/onc.2015.3. Epub 2015 Feb 9. PubMed PMID: 25659587; PubMed Central PMCID: PMC4530109.

[2]Raulf N, El-Attar R, Kulms D, Lecis D, Delia D, Walczak H, Papenfuss K, Odell E, Tavassoli M. Differential response of head and neck cancer cell lines to TRAIL or Smac mimetics is associated with the cellular levels and activity of caspase-8 and caspase-10. Br J Cancer. 2014 Nov 11;111(10):1955-64. doi: 10.1038/bjc.2014.521. Epub 2014 Oct 14. PubMed PMID: 25314064; PubMed Central PMCID: PMC4229641.

[3] Wu MS, Wang GF, Zhao ZQ, Liang Y, Wang HB, Wu MY, Min P, Chen LZ, Feng QS, Bei JX, Zeng YX, Yang D. Smac mimetics in combination with TRAIL selectively target cancer stem cells in nasopharyngeal carcinoma. Mol Cancer Ther. 2013 Sep;12(9):1728-37. doi: 10.1158/1535-7163.MCT-13-0017. Epub 2013 May 22. PubMed PMID: 23699656.

[4] Zhang S, Li G, Zhao Y, Liu G, Wang Y, Ma X, Li D, Wu Y, Lu J. Smac mimetic SM-164 potentiates APO2L/TRAIL- and doxorubicin-mediated anticancer activity in human hepatocellular carcinoma cells. PLoS One. 2012;7(12):e51461. doi: 10.1371/journal.pone.0051461. Epub 2012 Dec 11. PubMed PMID: 23240027; PubMed Central PMCID: PMC3519882.

[5] Zhou B, Zhang J, Chen G, You L, Zhang TP, Zhao YP. Therapy of Smac mimetic SM-164 in combination with gemcitabine for pancreatic cancer. Cancer Lett. 2013 Feb 1;329(1):118-24. doi: 10.1016/j.canlet.2012.10.039. Epub 2012 Nov 8. PubMed PMID: 23142291.

6: McComb S, Cheung HH, Korneluk RG, Wang S, Krishnan L, Sad S. cIAP1 and cIAP2 limit macrophage necroptosis by inhibiting Rip1 and Rip3 activation. Cell Death Differ. 2012 Nov;19(11):1791-801. doi: 10.1038/cdd.2012.59. Epub 2012 May 11. PubMed PMID: 22576661; PubMed Central PMCID: PMC3469059.7: Bai L, McEachern D, Yang CY, Lu J, Sun H, Wang S. LRIG1 modulates cancer cell sensitivity to Smac mimetics by regulating TNFα expression and receptor tyrosine kinase signaling. Cancer Res. 2012 Mar 1;72(5):1229-38. doi: 10.1158/0008-5472.CAN-11-2428. Epub 2012 Jan 12. PubMed PMID: 22241084; PubMed Central PMCID: PMC3294058.8: Yang D, Zhao Y, Li AY, Wang S, Wang G, Sun Y. Smac-mimetic compound SM-164 induces radiosensitization in breast cancer cells through activation of caspases and induction of apoptosis. Breast Cancer Res Treat. 2012 May;133(1):189-99. doi: 10.1007/s10549-011-1752-3. Epub 2011 Sep 7. PubMed PMID: 21901386.9: Lu J, McEachern D, Sun H, Bai L, Peng Y, Qiu S, Miller R, Liao J, Yi H, Liu M, Bellail A, Hao C, Sun SY, Ting AT, Wang S. Therapeutic potential and molecular mechanism of a novel, potent, nonpeptide, Smac mimetic SM-164 in combination with TRAIL for cancer treatment. Mol Cancer Ther. 2011 May;10(5):902-14. doi: 10.1158/1535-7163.MCT-10-0864. Epub 2011 Mar 3. PubMed PMID: 21372226; PubMed Central PMCID: PMC3091962.10: Yang J, McEachern D, Li W, Davis MA, Li H, Morgan MA, Bai L, Sebolt JT, Sun H, Lawrence TS, Wang S, Sun Y. Radiosensitization of head and neck squamous cell carcinoma by a SMAC-mimetic compound, SM-164, requires activation of caspases. Mol Cancer Ther. 2011 Apr;10(4):658-69. doi: 10.1158/1535-7163.MCT-10-0643. Epub 2011 Jan 31. PubMed PMID: 21282353; PubMed Central PMCID: PMC3073022.

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