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Merck
CN

SML3146

RHPS4 methosulfate

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C22H17F2N2 · CH3O4S
CAS Number:
390362-78-4
Molecular Weight:
458.48
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD30182275
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
protect from light

Key Documents

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Product Name

RHPS4 methosulfate, ≥98% (HPLC)

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

InChI key

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

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

faint brown to very dark brown-red

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000513541
0000513542
0000513542
0000513541
0000443525

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G-quadruplex DNA targeting alters class-switch recombination in B cells and attenuates allergic inflammation.
Zeinab Dalloul et al.
The Journal of allergy and clinical immunology, 142(4), 1352-1355 (2018-06-24)
PARP1 is activated at telomeres upon G4 stabilization: possible target for telomere-based therapy.
Salvati, et al.
Oncogene, 29, 6280-6293 (2010)
S M Gowan et al.
Molecular pharmacology, 60(5), 981-988 (2001-10-20)
A novel pentacyclic acridine, 3,11-difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate (RHPS4), has been identified as a potent inhibitor of telomerase in the cell-free telomeric repeat amplification protocol (TRAP). Modeling and biophysical studies suggest that RHPS4 inhibits telomerase through stabilization of four-stranded G-quadruplex structures formed
Robert A Heald et al.
Journal of medicinal chemistry, 45(3), 590-597 (2002-01-25)
Two short routes to novel methylated pentacyclic quinoacridinium salts have been devised. New compounds display telomerase-inhibitory potency (<1 microM) in the TRAP assay. 3,11-Difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate (12d, RHPS4, NSC 714187) has a higher selectivity for triplex and quadruplex DNA structures than
Annamaria Biroccio et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 17(8), 2227-2236 (2011-03-01)
We previously reported that the G-quadruplex (G4) ligand RHPS4 potentiates the antitumor activity of camptothecins both in vitro and in tumor xenografts. The present study aims at investigating the mechanisms involved in this specific drug interaction. Combination index test was
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