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End-stacking of copper cationic porphyrins on parallel-stranded guanine quadruplexes

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Abstract

Nucleic acids that contain multiple sequential guanines assemble into guanine quadruplexes (G-quadruplexes). Drugs that induce or stabilize G-quadruplexes are of interest because of their potential use as therapeutics. Previously, we reported on the interaction of the Cu2+ derivative of 5,10,15,20-tetrakis(1-methyl-4-pyridyl)-21H,23H-porphine (CuTMpyP4), with the parallel-stranded G-quadruplexes formed by d(T4G n T4) (n = 4 or 8) (Keating and Szalai in Biochemistry 43:15891–15900, 2004). Here we present further characterization of this system using a series of guanine-rich oligonucleotides: d(T4G n T4) (n = 5–10). Absorption titrations of CuTMpyP4 with all d(T4G n G4) quadruplexes produce approximately the same bathochromicity (8.3 ± 2 nm) and hypochromicity (46.2–48.6%) of the porphyrin Soret band. Induced emission spectra of CuTMpyP4 with d(T4G n T4)4 quadruplexes indicate that the porphyrin is protected from solvent. Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry revealed a maximum porphyrin to quadruplex stoichiometry of 2:1 for the shortest (n = 4) and longest (n = 10) quadruplexes. Electron paramagnetic resonance spectroscopy shows that bound CuTMpyP4 occupies magnetically noninteracting sites on the quadruplexes. Consistent with our previous model for d(T4G4T4), we propose that two CuTMpyP4 molecules are externally stacked at each end of the run of guanines in all d(T4G n T4) (n = 4–10) quadruplexes.

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Notes

  1. Note that throughout the manuscript [d(T4G n T4)4] corresponds to the tetramolecular quadruplex formed by association of four d(T4G n T4) strands.

Abbreviations

CD:

Circular dichroism

CuTMpyP4:

Cu2+ derivative of 5,10,15,20-tetrakis(1-methyl-4-pyridyl)-21H,23H-porphine

EPR:

Electron paramagnetic resonance

ESI:

Electrospray ionization

FTICR:

Fourier transform ion cyclotron resonance

G-quadruplex:

Guanine quadruplex

H2TMpyP4:

5,10,15,20-Tetrakis(1-methyl-4-pyridyl)-21H,23H-porphine

MS:

Mass spectrometry

Na2EDTA:

Ethylenediaminetetraacetic acid disodium salt

PAGE:

Polyacrylamide gel electrophoresis

TBE:

Tris(hydroxymethyl)aminomethane–borate–ethylenediaminetetraacetic acid

Tris:

Tris(hydroxymethyl)aminomethane

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Acknowledgments

This work was supported by a grant from Research Corporation (RI1053). Helpful discussions with Daniele Fabris and David H. Stewart are acknowledged.

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Correspondence to Veronika A. Szalai.

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Evans, S.E., Mendez, M.A., Turner, K.B. et al. End-stacking of copper cationic porphyrins on parallel-stranded guanine quadruplexes. J Biol Inorg Chem 12, 1235–1249 (2007). https://doi.org/10.1007/s00775-007-0292-0

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  • DOI: https://doi.org/10.1007/s00775-007-0292-0

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