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Safety Information

SML3146

Sigma-Aldrich

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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10 MG
¥16,400
50 MG
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About This Item

Empirical Formula (Hill Notation):
C22H17F2N2 · CH3O4S
CAS Number:
390362-78-4
Molecular Weight:
458.48
MDL number:
MFCD30182275
UNSPSC Code:
12352200
NACRES:
NA.77

¥16,400

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Request a Bulk Order

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

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML3146-50MG:
SML3146-BULK:
SML3146-VAR:
SML3146-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000200178
0000200179
0000200179
0000200178
0000136901

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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
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
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)
Gihan S Gunaratne et al.
PLoS neglected tropical diseases, 12(4), e0006420-e0006420 (2018-04-19)
The anthelmintic praziquantel (±PZQ) serves as a highly effective antischistosomal therapy. ±PZQ causes a rapid paralysis of adult schistosome worms and deleterious effects on the worm tegument. In addition to these activities against the parasite, ±PZQ also modulates host vascular
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