SML2696

RSM932A

Name: RSM932A
Brand: SIGMA
Price: 107 USD

≥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

Key Documents

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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

Related Categories

Bioactive Small Molecule Inhibitors

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This Item	SML1533	96738	76854
Sigma-Aldrich SML2696 RSM932A	Sigma-Aldrich SML1533 (±)-Marinopyrrole A	Sigma-Aldrich 96738 (R)-(+)-5,5′-Dichloro-2,2′-bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl	Sigma-Aldrich 76854 (S)-(−)-5,5′-Dichloro-2,2′-bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl
assay ≥97% (HPLC)	assay ≥95% (HPLC)	assay ≥95.0% (H-NMR)	assay ≥97.0% (H-NMR)
form powder	form powder	form crystals	form crystals
storage temp. 2-8°C	storage temp. −20°C	storage temp. -	storage temp. -
storage condition desiccated	storage condition -	storage condition -	storage condition -
solubility H₂O: 2 mg/mL, clear	solubility DMSO: 20 mg/mL, clear	solubility -	solubility -
color faint yellow to dark orange	color light yellow to dark yellow	color -	color -

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.

potent and selective choline kinase a (ChoKa, CHKA) inhibitor that induces apoptosis in cancer cells

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Near infrared fluorescent imaging of choline kinase alpha expression and inhibition in breast tumors.

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

Choline kinase inhibition induces exacerbated endoplasmic reticulum stress and triggers apoptosis via CHOP in cancer 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

Preclinical characterization of RSM-932A, a novel anticancer drug targeting the human choline kinase alpha, an enzyme involved in increased lipid metabolism of cancer cells.

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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RSM932A