A telomerase inhibitor
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RHPS4 (methyl sulfate)

Item No. 28543

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,11-difluorohydro-6,8,13-trimethyl-quino[4,3,2-kl]acridinium, methyl sulfate
CAS Number
390362-78-4
Molecular Formula
C22H17F2N2 • CH3SO4
Formula Weight
458.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
237, 294 nm
SMILES
FC1=CC=C(N(C)C2=CC(C)=CC3=C(C=C(F)C=C4)C4=[N+](C)C5=C23)C5=C1.O=S(OC)([O-])=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    RHPS4 is a telomerase inhibitor (IC50 = 0.33 µM).1 It is a ligand for the guanine quadruplex (G-quadruplex), a four-stranded DNA secondary structure formed from G-rich DNA sequences, that intercalates and stabilizes the G-quadruplex, which inhibits the activity of telomerase.1,2 RHPS4 (1 µM) induces phosphorylation of H2AX on telomeres, indicating telomeric DNA damage, in BJ fibroblasts expressing human telomerase.3 It inhibits cell growth in the NCI-60 panel of cancer cell lines (mean GI50 = 13.18 µM), as well as induces cell cycle arrest at the S-G2/M and apoptosis in M14 melanoma cells when used at concentrations ranging from 0.5 to 10 µM.4,5 RHPS4 (10 mg/kg) reduces tumor growth in several mouse xenograft models, including melanoma, lung, breast, and colon cancer models.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gowan, S.M., Heald, R., Stevens, M.F.G., et al. Potent inhibition of telomerase by small-molecule pentacyclic acridines capable of interacting with G-quadruplexes. Mol. Pharmacol. 60(5), 981-988 (2001).

    2. Ma, Y., Iida, K., and Nagasawa, K. Topologies of G-quadruplex: Biological functions and regulation by ligands. Biochem. Biophys. Res. Commun. 531(1), 3-17 (2020).

    3. Salvati, E., Leonetti, C., Rizzo, A., et al. Telomere damage induced by the G-quadruplex ligand RHPS4 has an antitumor effect. J. Clin. Invest. 117(11), 3236-3247 (2007).

    4. Heald, R.A., Modi, C., Cookson, J.C., et al. Antitumor polycyclic acridines. 8.1 Synthesis and telomerase-inhibitory activity of methylated pentacyclic acridinium salts. J. Med. Chem. 45(3), 590-597 (2002).

    5. Leonetti, C., Amodei, S., D'Angelo, C., et al. Biological activity of the G-quadruplex ligand RHPS4 (3,11-difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate) is associated with telomere capping alteration. Mol. Pharmacol. 66(5), 1138-1146 (2004).

    6. Leonetti, C., Scarsella, M., Riggio, G., et al. G-quadruplex ligand RHPS4 potentiates the antitumor activity of camptothecins in preclinical models of solid tumors. Clin. Cancer Res. 14(22), 7284-7291 (2008).