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SML3146

Sigma-Aldrich

RHPS4 methosulfate

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C22H17F2N2 · CH3O4S
CAS-Nummer:
390362-78-4
Molekulargewicht:
458.48
MDL-Nummer:
MFCD30182275
UNSPSC-Code:
12352200

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

protect from light

Farbe

faint brown to very dark brown-red

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

2-8°C

Inchi Code

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

InChIKey

VRWGYMXWYZBBGF-UHFFFAOYSA-M

SMILES String

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

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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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