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SML2696

Sigma-Aldrich

RSM932A

≥97% (HPLC)

Synonym(s):

1,1′-[[1,1′-Biphenyl]-4,4′-diylbis(methylene)]bis[4-[(4-chlorophenyl)methylamino]-quinolinium dibromide (9CI), 1,1′-[[[1,1′-Biphenyl]-4,4′-diyl]bis(methylene)]bis[4-[(4-chlorophenyl)methylamino]-quinolinium] bromide, RSM 932A, TCD-717

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About This Item

Empirical Formula (Hill Notation):
C46H38Cl2N4 · 2Br
CAS Number:
850807-63-5
Molecular Weight:
877.53
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

faint yellow to dark orange

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(C1=CC=[N+](CC2=CC=C(C3=CC=C(C[N+]4=CC=C(N(C5=CC=C(Cl)C=C5)C)C6=CC=CC=C46)C=C3)C=C2)C7=CC=CC=C17)C8=CC=C(Cl)C=C8

InChI

1S/C46H38Cl2N4/c1-49(39-23-19-37(47)20-24-39)43-27-29-51(45-9-5-3-7-41(43)45)31-33-11-15-35(16-12-33)36-17-13-34(14-18-36)32-52-30-28-44(42-8-4-6-10-46(42)52)50(2)40-25-21-38(48)22-26-40/h3-30H,31-32H2,1-2H3/q+2

InChI key

QGYGTMZEJNOHNU-UHFFFAOYSA-N

Biochem/physiol Actions

RSM932A is a potent and selective choline kinase a (ChoKa, CHKA) inhibitor that induces apoptosis in cancer cells via prolonged activation of ER stress response and C/EBP homologous protein (CHOP) overproduction. RSM932A decreases de novo in phosphatidylcholine synthesis and increases ceramides levels that selectively trigger apoptosis in cancer cells. On the other hand, RSM932A induces reversible G0/G1 cell cycle arrest in nontumorigenic cells. RSM932A exhibits potent antiproliferative activity in array of human cancer cell lines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Sean P Arlauckas et al.
Oncotarget, 8(10), 16518-16530 (2017-02-06)
Choline kinase alpha (ChoKα) overexpression is associated with an aggressive tumor phenotype. ChoKα inhibitors induce apoptosis in tumors, however validation of their specificity is difficult in vivo. We report the use of optical imaging to assess ChoKα status in cells
E Sanchez-Lopez et al.
Cell death & disease, 4, e933-e933 (2013-11-30)
Endoplasmic reticulum (ER) is a central organelle in eukaryotic cells that regulates protein synthesis and maturation. Perturbation of ER functions leads to ER stress, which has been previously associated with a broad variety of diseases. ER stress is generally regarded
Juan Carlos Lacal et al.
Molecular cancer therapeutics, 14(1), 31-39 (2014-12-10)
Choline kinase α (CHKA; here designated as ChoKα) is the first enzyme in the CDP-choline pathway, implicated in phospholipids metabolism. It is overexpressed in several human tumors such as breast, lung, bladder, colorectal, prostate, ovary, and liver. The overexpression of

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