Siramesine (Synonyms: Lu 28-179)

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Siramesine (Lu 28-179) is a potent sigma-2 receptor agonist. Siramesine has a subnanomolar affinity for sigma-2 receptors (IC₅₀=0.12 nM) and exhibits a 140-fold selectivity for sigma-2 receptors over sigma-1 receptors (IC₅₀=17 nM). Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Anti-cancer activity.

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Siramesine Chemical Structure

CAS No. : 147817-50-3

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Other In-stock Forms of Siramesine:

Siramesine hydrochloride

Other Forms of Siramesine:

Siramesine hydrochloride In-stock
Siramesine fumarate Get quote

4 Publications Citing Use of MCE Siramesine

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Biological Activity
Purity & Documentation
References
Customer Review

Description

Cellular Effect

Cell Line	Type	Value	Description	References
C6	EC₅₀	43.1 μM Compound: Lu-28-179	Antiproliferative activity against rat C6 cells assessed as reduction in cell viability after 24 hrs by MTT assay Antiproliferative activity against rat C6 cells assessed as reduction in cell viability after 24 hrs by MTT assay	10.1039/C5MD00079C
DU-145	EC₅₀	13.9 μM Compound: Lu-28-179	Antiproliferative activity against human DU145 cells assessed as reduction in cell viability after 24 hrs by MTT assay Antiproliferative activity against human DU145 cells assessed as reduction in cell viability after 24 hrs by MTT assay	10.1039/C5MD00079C
EMT6	EC₅₀	14.9 μM Compound: 6	Antagonist activity at sigma-2 receptor in mouse EMT6 cells assessed as inhibition of cell proliferation after 24 hrs by MTS assay Antagonist activity at sigma-2 receptor in mouse EMT6 cells assessed as inhibition of cell proliferation after 24 hrs by MTS assay	[PMID: 24821398]
EMT6	EC₅₀	5.3 μM Compound: 6	Antagonist activity at sigma-2 receptor in mouse EMT6 cells assessed as inhibition of cell proliferation after 48 hrs by MTS assay Antagonist activity at sigma-2 receptor in mouse EMT6 cells assessed as inhibition of cell proliferation after 48 hrs by MTS assay	[PMID: 24821398]
MCF7	EC₅₀	12.3 μM Compound: Lu-28-179	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 48 hrs by MTT assay	10.1039/C5MD00079C
MCF7	IC₅₀	13 μM Compound: Srms	Cytotoxicity against ER/PR-positive HER2-negative human MCF7 cells harbouring p53 R175H mutant assessed as inhibition of cell growth incubated for 48 hrs by resazurin dye based assay Cytotoxicity against ER/PR-positive HER2-negative human MCF7 cells harbouring p53 R175H mutant assessed as inhibition of cell growth incubated for 48 hrs by resazurin dye based assay	[PMID: 35724925]
MCF7	EC₅₀	23.6 μM Compound: Lu-28-179	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 24 hrs by MTT assay Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 24 hrs by MTT assay	10.1039/C5MD00079C
SK-BR-3	IC₅₀	14 μM Compound: Srms	Cytotoxicity against ER/PR-negative HER2-positive human SK-BR-3 cells harbouring wild type p53 assessed as inhibition of cell growth incubated for 48 hrs by resazurin dye based assay Cytotoxicity against ER/PR-negative HER2-positive human SK-BR-3 cells harbouring wild type p53 assessed as inhibition of cell growth incubated for 48 hrs by resazurin dye based assay	[PMID: 35724925]

In Vitro

Siramesine displays the binding affinities: IC₅₀ (sigma 1)=17 nM, IC₅₀ (sigma 2)=0.12 nM, IC₅₀ (5-HT_1A)=21000 nM, IC₅₀ (5-HT_1A)=2000 nM, IC₅₀ (D₂)=800 nM, IC₅₀ (alpha 1)=330 nM^[1].
Siramesine (0-50μM; 8 hours) induces cell death in various cell lines (HaCaT, Hsc-4, HeLa and MCF-7, neuroblastoma cell line SH-SY5Y and glioblastoma cell line U-87MG)^[2].
Siramesine (0-40 μM; 2-48 hours) activates caspases in HaCaT and in U-87MG cells^[2].

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

Molecular Weight

454.58

Formula

C₃₀H₃₁FN₂O

CAS No.

147817-50-3

SMILES

FC1=CC=C(N2C=C(CCCCN3CCC4(CC3)OCC5=C4C=CC=C5)C6=C2C=CC=C6)C=C1

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Perregaard J, et al. Sigma ligands with subnanomolar affinity and preference for the sigma 2 binding site. 1. 3-(omega-aminoalkyl)-1H-indoles. J Med Chem. 1995;38(11):1998-2008. [Content Brief]

[2]. Česen MH, et al. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes. Cell Death Dis. 2013;4(10):e818. Published 2013 Oct 3. [Content Brief]

[3]. Ostenfeld MS, et al. Anti-cancer agent siramesine is a lysosomotropic detergent that induces cytoprotective autophagosome accumulation. Autophagy. 2008;4(4):487-499. [Content Brief]

Siramesine Related Classifications

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

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

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

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Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Siramesine147817-50-3Lu 28-179Sigma ReceptorcancerselectivitydeathcathepsinmitochondrialysosomesInhibitorinhibitorinhibit

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