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Two cationic porphyrin isomers showing different multimeric G-quadruplex recognition specificity against monomeric G-quadruplexes.

Huang XX, Zhu LN, Wu B, Huo YF, Duan NN, Kong DM - Nucleic Acids Res. (2014)

Bottom Line: Ligands that can interact specifically with telomeric multimeric G-quadruplexes could be developed as promising anticancer drugs with few side effects related to other G-quadruplex-forming regions.These results provide important information for the design of highly specific multimeric G-quadruplex ligands.Another interesting finding is that pocket size is an important factor in determining the stability of multimeric G-quadruplexes.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin 300071, PR China Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, PR China.

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The chemical structures of p-TMPipEOPP and m-TMPipEOPP.
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Figure 4: The chemical structures of p-TMPipEOPP and m-TMPipEOPP.

Mentions: Recently, we designed a cationic porphyrin derivative with four large side arm substituents, 5,10,15,20-tetra-{4-[2-(1-methyl-1-piperidinyl)ethoxy] phenyl} porphyrin (p-TMPipEOPP; Scheme 1), and the possibility of this derivative acting as a ligand of multimeric G-quadruplexes was investigated under molecular crowding conditions (47). The results showed this porphyrin derivative could promote the formation of multimeric G-quadruplexes and stabilize them. p-TMPipEOPP lacks the ability to distinguish between multimeric and monomeric G-quadruplexes, however, implying the telomeric region is not the sole target of this ligand. In this study, we synthesized another cationic porphyrin derivative, 5,10,15,20-tetra-{3-[2-(1-methyl-1-piperidinyl)ethoxy] phenyl} porphyrin (m-TMPipEOPP; Scheme 1). m-TMPipEOPP and p-TMPipEOPP are isomers. The slight change of structure accounts for m-TMPipEOPP with a higher level of selectivity for multimeric G-quadruplexes compared to p-TMPipEOPP. Different binding modes to multimeric G-quadruplexes formed by several telomeric sequences with different lengths and their mutants were proposed for these two porphyrin derivatives on the basis of comparison of their binding behavior.


Two cationic porphyrin isomers showing different multimeric G-quadruplex recognition specificity against monomeric G-quadruplexes.

Huang XX, Zhu LN, Wu B, Huo YF, Duan NN, Kong DM - Nucleic Acids Res. (2014)

The chemical structures of p-TMPipEOPP and m-TMPipEOPP.
© Copyright Policy - creative-commons
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4117758&req=5

Figure 4: The chemical structures of p-TMPipEOPP and m-TMPipEOPP.
Mentions: Recently, we designed a cationic porphyrin derivative with four large side arm substituents, 5,10,15,20-tetra-{4-[2-(1-methyl-1-piperidinyl)ethoxy] phenyl} porphyrin (p-TMPipEOPP; Scheme 1), and the possibility of this derivative acting as a ligand of multimeric G-quadruplexes was investigated under molecular crowding conditions (47). The results showed this porphyrin derivative could promote the formation of multimeric G-quadruplexes and stabilize them. p-TMPipEOPP lacks the ability to distinguish between multimeric and monomeric G-quadruplexes, however, implying the telomeric region is not the sole target of this ligand. In this study, we synthesized another cationic porphyrin derivative, 5,10,15,20-tetra-{3-[2-(1-methyl-1-piperidinyl)ethoxy] phenyl} porphyrin (m-TMPipEOPP; Scheme 1). m-TMPipEOPP and p-TMPipEOPP are isomers. The slight change of structure accounts for m-TMPipEOPP with a higher level of selectivity for multimeric G-quadruplexes compared to p-TMPipEOPP. Different binding modes to multimeric G-quadruplexes formed by several telomeric sequences with different lengths and their mutants were proposed for these two porphyrin derivatives on the basis of comparison of their binding behavior.

Bottom Line: Ligands that can interact specifically with telomeric multimeric G-quadruplexes could be developed as promising anticancer drugs with few side effects related to other G-quadruplex-forming regions.These results provide important information for the design of highly specific multimeric G-quadruplex ligands.Another interesting finding is that pocket size is an important factor in determining the stability of multimeric G-quadruplexes.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin 300071, PR China Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, PR China.

Show MeSH
Related in: MedlinePlus