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SML3146

Sigma-Aldrich

RHPS4 methosulfate

≥98% (HPLC)

Sinónimos:

3,11-Difluoro-6,8,13-trimethyl-8H-quino[4,3,2,kl]acridinium methosulfate, NSC 714187, Quino[4,3,2-kl]acridinium, 3,11-difluorohydro-6,8,13-trimethyl-, methyl sulfate (1:1)

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About This Item

Fórmula empírica (notación de Hill):
C22H17F2N2 · CH3O4S
Número de CAS:
390362-78-4
Peso molecular:
458.48
Número MDL:
MFCD30182275
Código UNSPSC:
12352200
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

protect from light

color

faint brown to very dark brown-red

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

2-8°C

cadena SMILES

FC1=CC=C(N(C)C2=C3C4=[N+](C)C5=C(C=C(F)C=C5)C3=CC(C)=C2)C4=C1.[O-]S(=O)(OC)=O

InChI

1S/C22H17F2N2.CH4O4S/c1-12-8-16-15-10-13(23)4-6-18(15)26(3)22-17-11-14(24)5-7-19(17)25(2)20(9-12)21(16)22;1-5-6(2,3)4/h4-11H,1-3H3;1H3,(H,2,3,4)/q+1;/p-1

Clave InChI

VRWGYMXWYZBBGF-UHFFFAOYSA-M

Acciones bioquímicas o fisiológicas

G-quadruplex (G4)-targeting telomerase inhibitor with anti-cancer efficacy in cultures and in vivo.
RHPS4 is a pentacyclic acridine compound that exerts telomerase inhibitory activity (IC50 = 330 nM by TRAP assay) via targeting telomeric DNA G-quadruplex (G4) structure, causing alteration in the telomeric architecture and telomere dysfunction. RHPS4 induces cell cycle arrest and growth inhibition in cancer cultures in vitro(% GI/culture/time = 93%/21NT/15 days, 67%/A431/12 days, 91%/GM847/15 days; 200 nM replenish twice weekly) and exhibits anti-tumor efficacy in mice in vivo (10-15 mg/kg/d iv.). RHPS4 is also reproted to target mitochondrial DNA (mtDNA) G4 structures, perturbing mitochondrial genome replication, transcription processivity, and respiratory function.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Erica Salvati et al.
The Journal of clinical investigation, 117(11), 3236-3247 (2007-10-13)
Functional telomeres are required for the replicability of cancer cells. The G-rich strand of telomeric DNA can fold into a 4-stranded structure known as the G-quadruplex (G4), whose stabilization alters telomere function limiting cancer cell growth. Therefore, the G4 ligand
Carlo Leonetti et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 14(22), 7284-7291 (2008-11-18)
The formation of G-quadruplex structures at telomeric DNA sequences blocks telomerase activity, offering an original strategy to design and develop new antitumor agents. The pentacyclic acridinium salt RHPS4 is one of the most effective and selective G4 ligands able to
Carlo Leonetti et al.
Molecular pharmacology, 66(5), 1138-1146 (2004-08-12)
This study had two goals: 1) to evaluate the biological effect of the novel pentacyclic acridine 3,11-difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate (RHPS4) on human melanoma lines possessing long telomeres, and 2) to elucidate the relationship between G-quadruplex-based telomerase inhibitor-induced cellular effects and telomere

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