A telomerase inhibitor
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TMPyP4 (tosylate)

Item No. 18474

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,4',4'',4'''-(21H,23H-porphine-5,10,15,20-tetrayl)tetrakis[1-methyl-pyridinium], 4-methylbenzenesulfonate (1:4)
CAS Number
36951-72-1
Synonyms
  • TMP-1363
  • TMPyP4 4-methylbenzenesulfonate
Molecular Formula
C44H38N8 • 4C7H7O3S
Formula Weight
1363.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
219, 261, 423 nm
SMILES
C[N+]1=CC=C(/C2=C3N/C(C=C/3)=C(C4=N/C(C=C4)=C(C5=CC=C(/C(C6=CC=[N+](C=C6)C)=C7C=CC2=N/7)N5)/C8=CC=[N+](C=C8)C)/C9=CC=[N+](C=C9)C)C=C1.CC%10=CC=C(C=C%10)S([O-])(=O)=O.CC%11=CC=C(C=C%11)S([O-])(=O)=O.CC%12=CC=C(C=C%12)S([O-])(=O)=O.CC%13=CC=C(C=C%13)S(
InChi Code
InChI=1S/C44H37N8.4C7H8O3S/c1-49-21-13-29(14-22-49)41-33-5-7-35(45-33)42(30-15-23-50(2)24-16-30)37-9-11-39(47-37)44(32-19-27-52(4)28-20-32)40-12-10-38(48-40)43(36-8-6-34(41)46-36)31-17-25-51(3)26-18-31;4*1-6-2-4-7(5-3-6)11(8,9)10/h5-28H,1-4H3,(H,45,4
InChi Key
AKZFRMNXBLFDNN-GVHKZQBISA-K
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    250 mg

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    500 mg

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    Cayman Chemical
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    Product Description

    TMPyP4 is a cationic porphyrin that intercalates into and stabilizes G-quadruplexes, which are formed by DNA and RNA sequences composed of blocks of guanine residues.1 In this way, TMPyP4 inhibits telomerase activity (IC50 ≤ 50 µM), blocking the clonogenic growth and migration of cancer cells in culture and in vivo.2,3,4 TMPyP4 also inhibits acetylcholinesterase at doses of 0.1 to 1.0 mM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiel, R.J., Howard, J.C., Mark, E.H., et al. Interaction of DNA with a porphyrin ligand: Evidence for intercalation. Nucleic Acids Res. 6(9), 3093-3118 (1979).

    2. Izbicka, E., Wheelhouse, R.T., Raymond, E., et al. Effects of cationic porphyrins as G-quadruplex interactive agents in human tumor cells. Cancer Res. 59, 639-644 (1999).

    3. Rapozzi, V., Zorzet, S., Zacchigna, M., et al. Anticancer activity of cationic porphyrins in melanoma tumour-bearing mice and mechanistic in vitro studies. Mol. Cancer 13, 75 (2014).

    4. Rha, S.Y., Izbicka, E., Lawrence, R., et al. Effect of telomere and telomerase interactive agents on human tumor and normal cell lines. Clin. Cancer Res. 6, 987-993 (2000).

    5. Fujiwara, N., Mazzola, M., Cai, E., et al. TMPyP4, a stabilizer of nucleic acid secondary structure, is a novel acetylcholinesterase inhibitor. PLoS One 10(9), e0139167 (2015).