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MedKoo Cat#: 407187 | Name: SM-164
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Description:

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

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.

Chemical Structure

SM-164
SM-164
CAS#957135-43-2

Theoretical Analysis

MedKoo Cat#: 407187

Name: SM-164

CAS#: 957135-43-2

Chemical Formula: C62H84N14O6

Exact Mass: 1120.6698

Molecular Weight: 1121.45

Elemental Analysis: C, 66.40; H, 7.55; N, 17.49; O, 8.56

Price and Availability

Size Price Availability Quantity
5mg USD 650.00 2 Weeks
10mg USD 1,000.00 2 Weeks
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Related CAS #
No Data
Synonym
SM 164; SM164; SM-164.
IUPAC/Chemical Name
(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)
InChi Key
LGYDZXNSSLRFJS-IOQQVAQYSA-N
InChi Code
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
SMILES Code
O=C1N2[C@@](CC[C@H]2C(N[C@H](C3=CN(CCCCC4=CC=C(CCCCN5N=NC([C@@H](NC([C@H](CC[C@@]6(CCCC7)[H])N6C([C@H]7NC([C@@H](NC)C)=O)=O)=O)C8=CC=CC=C8)=C5)C=C4)N=N3)C9=CC=CC=C9)=O)([H])CCCC[C@@H]1NC([C@H](C)NC)=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
>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:
SM-164 is a cell-permeable Smac mimetic compound. SM-164 binds to XIAP protein containing both the BIR2 and BIR3 domains with an IC50 value of 1.39 nM and functions as an extremely potent antagonist of XIAP.
In vitro activity:
The study proposes that Smac mimetics, including SM-164, show potential as therapeutic agents for hepatocellular carcinoma (HCC). While SM-164 alone has weak effects on HCC cell viability, it significantly enhances the anticancer activity of Apo2 ligand or TNF-related apoptosis-inducing ligand (APO2L/TRAIL) and Doxorubicin in HCC cells. Combining SM-164 with chemotherapeutic agents activates caspases-9, -3, cleaves poly ADP-ribose polymerase (PARP), and reduces AKT activation. Reference: PLoS One. 2012;7(12):e51461. https://pubmed.ncbi.nlm.nih.gov/23240027/
In vivo activity:
SM-164 showed protective effects in anti-neutrophil cytoplasmic antibody-associated vasculitis (AAV) by enhancing intracellular fatty acid oxidation in neutrophils. In an experimental autoimmune vasculitis (EAV) rat model, SM164 significantly reduced renal injury. SM-164 inhibited neutrophil activation induced by MPO-ANCA positive IgG or serum from MPO-AAV patients. SM-164 also reduced neutrophil adhesion to endothelial cells. Reference: Rheumatology (Oxford). 2023 Jul 5;62(7):2563-2573. https://pubmed.ncbi.nlm.nih.gov/36308438/
Solvent mg/mL mM comments
Solubility
DMSO 25.0 22.29
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 1,121.45 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. Liu X, Yao JJ, Chen Z, Lei W, Duan R, Yao Z. Lipopolysaccharide sensitizes the therapeutic response of breast cancer to IAP antagonist. Front Immunol. 2022 Aug 31;13:906357. doi: 10.3389/fimmu.2022.906357. PMID: 36119107; PMCID: PMC9471085. 2. 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. PMID: 23240027; PMCID: PMC3519882. 3. Wang LY, Wang RX, Wang C, Chen SF, Sun XJ, Li ZY, Chen M, Little MA, Zhao MH. Inhibitor of apoptosis proteins antagonist SM164 ameliorates experimental MPO-ANCA-associated vasculitis via enhancing fatty acid oxidation in neutrophils. Rheumatology (Oxford). 2023 Jul 5;62(7):2563-2573. doi: 10.1093/rheumatology/keac621. PMID: 36308438. 4. Lei W, Duan R, Li J, Liu X, Huston A, Boyce BF, Yao Z. The IAP Antagonist SM-164 Eliminates Triple-Negative Breast Cancer Metastasis to Bone and Lung in Mice. Sci Rep. 2020 Apr 24;10(1):7004. doi: 10.1038/s41598-020-64018-z. PMID: 32332865; PMCID: PMC7181667.
In vitro protocol:
1. Liu X, Yao JJ, Chen Z, Lei W, Duan R, Yao Z. Lipopolysaccharide sensitizes the therapeutic response of breast cancer to IAP antagonist. Front Immunol. 2022 Aug 31;13:906357. doi: 10.3389/fimmu.2022.906357. PMID: 36119107; PMCID: PMC9471085. 2. 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. PMID: 23240027; PMCID: PMC3519882.
In vivo protocol:
1. Wang LY, Wang RX, Wang C, Chen SF, Sun XJ, Li ZY, Chen M, Little MA, Zhao MH. Inhibitor of apoptosis proteins antagonist SM164 ameliorates experimental MPO-ANCA-associated vasculitis via enhancing fatty acid oxidation in neutrophils. Rheumatology (Oxford). 2023 Jul 5;62(7):2563-2573. doi: 10.1093/rheumatology/keac621. PMID: 36308438. 2. Lei W, Duan R, Li J, Liu X, Huston A, Boyce BF, Yao Z. The IAP Antagonist SM-164 Eliminates Triple-Negative Breast Cancer Metastasis to Bone and Lung in Mice. Sci Rep. 2020 Apr 24;10(1):7004. doi: 10.1038/s41598-020-64018-z. PMID: 32332865; PMCID: PMC7181667.
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):5472-81. 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.