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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
MDL number:
MFCD30182275
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

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

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 Actions

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
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
P Phatak et al.
British journal of cancer, 96(8), 1223-1233 (2007-04-05)
The pentacyclic acridinium methosulfate salt RHPS4 induces the 3'single-stranded guanine-rich telomeric overhang to fold into a G-quadruplex structure. Stabilisation of the latter is incompatible with an attachment of telomerase to the telomere and thus G-quadruplex ligands can effectively inhibit both
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