SIRAMESINE Chemical Properties

Boiling point:

611.4±55.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO (up to at least 25 mg/ml)

pka

9.45±0.20(Predicted)

form 

solid

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChI

InChI=1S/C30H31FN2O/c31-25-12-14-26(15-13-25)33-21-23(27-9-2-4-11-29(27)33)7-5-6-18-32-19-16-30(17-20-32)28-10-3-1-8-24(28)22-34-30/h1-4,8-15,21H,5-7,16-20,22H2

InChIKey

XWAONOGAGZNUSF-UHFFFAOYSA-N

SMILES

C12(CCN(CCCCC3C4=C(N(C5=CC=C(F)C=C5)C=3)C=CC=C4)CC1)C1=C(C=CC=C1)CO2

SIRAMESINE Usage And Synthesis

Description

Siramesine (Lu 28-179, 147817-50-3) is a σ2 selective agonist(IC50’s: σ1 = 17nM, σ2 = 0.2nM).1It produced non-sedating potent and long-last anxiolytic effects in rodents.2Siramesine induced caspase-independent programmed cell death in various cancer cell linesviaincreased levels of ROS and lysosomal leakage.3,4,5Mitochondrial destabilization via loss of membrane potential and increased ROS has also been offered as a mechanism of action for the triggering of cell death by Siramesine.6

Uses

Treatment of prostate cancer.

brand name

Provenge (Dendreon).

IC 50

Sigma 1 Receptor

References

[1] JENS PERREGAARD. .sigma. Ligands with Subnanomolar Affinity and Preference for the .sigma.2 Binding Site. 1. 3-(.omega.-Aminoalkyl)-1H-indoles[J]. Journal of Medicinal Chemistry, 1995, 38 11: 1998-2008. DOI:10.1021/jm00011a019
[2] C SÁNCHEZ. The selective sigma2-ligand Lu 28-179 has potent anxiolytic-like effects in rodents.[J]. Journal of Pharmacology and Experimental Therapeutics, 1997, 283 3: 1323-1332.
[3] MARIE STAMPE OSTENFELD. Effective tumor cell death by sigma-2 receptor ligand siramesine involves lysosomal leakage and oxidative stress.[J]. Cancer research, 2005, 65 19: 8975-8983. DOI:10.1158/0008-5472.can-05-0269
[4] MARIE STAMPE OSTENFELD. Anti-cancer agent siramesine is a lysosomotropic detergent that induces cytoprotective autophagosome accumulation.[J]. Autophagy, 2008: 487-499. DOI:10.4161/auto.5774
[5] R F DIELSCHNEIDER. Lysosomotropic agents selectively target chronic lymphocytic leukemia cells due to altered sphingolipid metabolism[J]. Leukemia, 2016, 30 6: 1290-1300. DOI:10.1038/leu.2016.4
[6] M HAFNER ČESEN. Siramesine triggers cell death through destabilisation of mitochondria, but not lysosomes[J]. Cell Death & Disease, 2013, 4 10: e818-e818. DOI:10.1038/cddis.2013.361

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