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Molecules 2012, 17(9), 10586-10613; doi:10.3390/molecules170910586
Review

Specific Binding of Anionic Porphyrin and Phthalocyanine to the G-Quadruplex with a Variety of in Vitro and in Vivo Applications

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Received: 31 July 2012; in revised form: 27 August 2012 / Accepted: 29 August 2012 / Published: 5 September 2012
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanine)
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Abstract: The G-quadruplex, a four-stranded DNA structure with stacked guanine tetrads (G-quartets), has recently been attracting attention because of its critical roles in vitro and in vivo. In particular, the G-quadruplex functions as ligands for metal ions and aptamers for various molecules. Interestingly, the G-quadruplex can show peroxidase-like activity with an anionic porphyrin, iron (III) protoporphyrin IX (hemin). Importantly, hemin binds to G-quadruplexes with high selectivity over single-stranded DNA (ssDNA) and double-stranded DNA (dsDNA), which is attributable to an electrostatic repulsion of phosphate groups in ssDNA and dsDNA. The G-quadruplex and hemin-G-quadruplex complex allow development of sensing techniques to detect DNA, metal ions and proteins. In addition to hemin, anionic phthalocyanines also bind to the G-quadruplex formed by human telomere DNA, specifically over ssDNA and dsDNA. Since the binding of anionic phthalocyanines to the G-quadruplex causes an inhibition of telomerase activity, which plays a role in the immortal growth of cancer cells, anionic phthalocyanines are promising as novel anticancer drug candidates. This review focuses on the specific binding of hemin and anionic phthalocyanines to G-quadruplexes and the applications in vitro and in vivo of this binding property.
Keywords: anionic phthalocyanine; DNAzyme; G-quadruplex; hemin; peroxidase; telomerase anionic phthalocyanine; DNAzyme; G-quadruplex; hemin; peroxidase; telomerase
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yaku, H.; Murashima, T.; Miyoshi, D.; Sugimoto, N. Specific Binding of Anionic Porphyrin and Phthalocyanine to the G-Quadruplex with a Variety of in Vitro and in Vivo Applications. Molecules 2012, 17, 10586-10613.

AMA Style

Yaku H, Murashima T, Miyoshi D, Sugimoto N. Specific Binding of Anionic Porphyrin and Phthalocyanine to the G-Quadruplex with a Variety of in Vitro and in Vivo Applications. Molecules. 2012; 17(9):10586-10613.

Chicago/Turabian Style

Yaku, Hidenobu; Murashima, Takashi; Miyoshi, Daisuke; Sugimoto, Naoki. 2012. "Specific Binding of Anionic Porphyrin and Phthalocyanine to the G-Quadruplex with a Variety of in Vitro and in Vivo Applications." Molecules 17, no. 9: 10586-10613.



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