SM-164 hydrochloride

Name: SM-164 hydrochloride
Brand: MedChemExpress
SKU: HY-15989A
Rating: 5.0 (38 reviews)

Cat. No.: HY-15989A Purity: 98.10%: FAQs
Data Sheet SDS COA Handling Instructions

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SM-164 hydrochloride 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.

For research use only. We do not sell to patients.

SM-164 hydrochloride Chemical Structure

CAS No. : 2734174-02-6

Size	Price	Stock	Quantity
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in Water ready for reconstitution	USD 764	In-stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in Water	USD 764	In-stock	Estimated Time of Arrival: December 31
Solid
5 mg	USD 350	In-stock	Estimated Time of Arrival: December 31
10 mg	USD 600	In-stock	Estimated Time of Arrival: December 31
50 mg	USD 1800	In-stock	Estimated Time of Arrival: December 31
100 mg		Get quote
200 mg		Get quote

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Customer Review

Based on 38 publication(s) in Google Scholar

Other Forms of SM-164 hydrochloride:

SM-164 In-stock

36 Publications Citing Use of MCE SM-164 hydrochloride

: SM-164 hydrochloride purchased from MedChemExpress. Usage Cited in: Biomed Res Int. 2019 Apr 7;2019:2121357. [Abstract]; The mouse alveolar epithelium cell line MLE12 is exposed to SM-164 for 24h with or without LPS for 24h. RIPK3 and MLKL are downregulated along with the inhibition of cIAP2 by SM-164 during LPS-induced ARDS.

: SM-164 hydrochloride purchased from MedChemExpress. Usage Cited in: Cell Death Dis. 2018 Nov 15;9(12):1140. [Abstract]; MEF cells are transfected with indicated siRNA for 3 days and then treated with TNF+Smac+zVAD, or poly I:C+zVAD for 3 h.

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View All Isoforms

cIAP cIAP-1 cIAP-2 XIAP

Biological Activity
Protocol
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target^[1]^[2]

cIAP-1

0.31 nM (Ki)

cIAP-2

1.1 nM (Ki)

cIAP

In Vitro

SM-164 is a non-peptide, cell-permeable, bivalent small-molecule, which mimics Smac protein for targeting XIAP. SM-164 binds to XIAP containing both BIR domains with an IC₅₀ value of 1.39 nM, being 300 and 7000-times more potent than its monovalent counterparts and the natural Smac AVPI peptide, respectively. SM-164 concurrently interacts with both BIR domains in XIAP and functions as an ultra-potent antagonist of XIAP in both cell-free functional and cell-based assays. SM-164 targets cellular XIAP and effectively induces apoptosis at concentrations as low as 1 nM in leukemia cancer cells, while having a minimal toxicity to normal human primary cells at 10,000 nM^[1]. The binding affinities of SM-164 to XIAP, cIAP-1, and cIAP-2 proteins are determined using fluorescence-polarization based assays. SM-164 has a K_i value of 0.56 nM to XIAP protein containing both BIR2 and BIR3 domains. SM-164 has a K_i value of 0.31 nM to cIAP-1 protein containing both BIR2 and BIR3 domains. SM-164 binds to cIAP-2 BIR3 protein with K_i values of 1.1 nM. Addition of exogenous TNFα can significantly enhance the activity of these Smac mimetics, especially for SM-164, in resistant cancer cell lines such as HCT116 and MDA-MB-453^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

SM-164 is evaluated for its ability to inhibit tumor growth. SM-164 is highly effective in inhibition of tumor growth and capable of achieving tumor regression in the MDA-MB-231 xenograft model. Treatment with SM-164 at 1 mg/kg completely inhibits tumor growth during the treatment. Treatment with SM-164 at 5 mg/kg reduces the tumor volume from 147±54 mm³ at the beginning of the treatment (day 25) to 54±32 mm³ at the end of the treatment (day 36), a reduction of 65%. The strong antitumor activity by SM-164 is long lasting and not transient. SM-164 at 5 mg/kg is statistically more effective than Taxotere at the end of the treatment (P<0.01) or when the tumor size in the control group reaches 750 mm³ (P<0.02)^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

1157.88

Formula

C₆₂H₈₅ClN₁₄O₆

CAS No.

2734174-02-6

Appearance

Solid

Color

White to off-white

SMILES

C[C@H](NC)C(N[C@H]1CCCC[C@](CC[C@H]2C(N[C@@H](C3=CC=CC=C3)C4=CN(CCCCC5=CC=C(CCCCN6N=NC([C@@H](NC([C@@H]7CC[C@@](CCCC[C@@H]8NC([C@@H](NC)C)=O)([H])N7C8=O)=O)C9=CC=CC=C9)=C6)C=C5)N=N4)=O)([H])N2C1=O)=O.Cl

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

Solvent & Solubility

In Vitro:

H₂O : ≥ 106 mg/mL (91.55 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	0.8636 mL	4.3182 mL	8.6365 mL
5 mM	0.1727 mL	0.8636 mL	1.7273 mL
10 mM	0.0864 mL	0.4318 mL	0.8636 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: PBS
Solubility: 50 mg/mL (43.18 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).

Purity & Documentation

Purity: 98.10%

Select Batch:

Data Sheet (281 KB) SDS (251 KB)

COA (251 KB) LCMS (99 KB)

Handling Instructions (2659 KB)

References

[1]. Sun H, et al. Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J Am Chem Soc. 2007 Dec 12;129(49):15279-94. [Content Brief]

[2]. Lu J, et al. SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP. Cancer Res. 2008 Nov 15;68(22):9384-93. [Content Brief]

Kinase Assay ^[2]	A set of sensitive and quantitative fluorescence polarization (FP)-based assays are developed to determine the binding affinities of our designed Smac mimetics to XIAP BIR3, XIAP containing both BIR2 and BIR3 domains, cIAP-1 BIR3, cIAP-1 containing both BIR2 and BIR3 domains, and cIAP-2 protein. The FP-based assay for XIAP BIR3 protein is measured. Briefly, 5-carboxyfluorescein is coupled to the lysine side chain of a mutated Smac peptide with the sequence (AbuRPFK-Fam) and this fluorescently tagged peptide (named SM5F) is used as the fluorescent tracer in FP-based binding assay to XIAP BIR3. The K_d value of this fluorescent tracer is determined to be 17.9 nM to XIAP BIR3. In competitive binding experiments, a tested compound is incubated with 30 nM of XIAP BIR3 protein and 5 nM of SM5F in the assay buffer (100 mM potassium phosphate, pH 7.5; 100μg/mL bovine gamma globulin; 0.02 % sodium azide)^[2]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Cell Assay ^[2]	HCT116 colon cancer cells are treated with SM-164 (1, 10, and 100 nM) alone, TNFα alone, or the combination for 48 h. Cell growth inhibition is determined by a WST assay^[2]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal Administration ^[2]	Mice^[2] SCID mice (8-10 per group) bearing MDA-MB-231 xenograft tumors are treated i.v. with 1 and 5 mg/kg of SM-164 or 7.5 mg/kg of Taxotere or vehicle control daily, 5 d/wk for 2 wk. Tumor sizes and animal weights are measured thrice a week^[2]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
References	[1]. Sun H, et al. Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J Am Chem Soc. 2007 Dec 12;129(49):15279-94. [Content Brief] [2]. Lu J, et al. SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP. Cancer Res. 2008 Nov 15;68(22):9384-93. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

H₂O	1 mM	0.8636 mL	4.3182 mL	8.6365 mL	21.5912 mL
	5 mM	0.1727 mL	0.8636 mL	1.7273 mL	4.3182 mL
	10 mM	0.0864 mL	0.4318 mL	0.8636 mL	2.1591 mL
	15 mM	0.0576 mL	0.2879 mL	0.5758 mL	1.4394 mL
	20 mM	0.0432 mL	0.2159 mL	0.4318 mL	1.0796 mL
	25 mM	0.0345 mL	0.1727 mL	0.3455 mL	0.8636 mL
	30 mM	0.0288 mL	0.1439 mL	0.2879 mL	0.7197 mL
	40 mM	0.0216 mL	0.1080 mL	0.2159 mL	0.5398 mL
	50 mM	0.0173 mL	0.0864 mL	0.1727 mL	0.4318 mL
	60 mM	0.0144 mL	0.0720 mL	0.1439 mL	0.3599 mL
	80 mM	0.0108 mL	0.0540 mL	0.1080 mL	0.2699 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.