Literature DB >> 16734413

Formation of a complex of 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)-21H,23H-porphyrin with G-quadruplex DNA.

Hajime Mita1, Takako Ohyama, Yoshiyuki Tanaka, Yasuhiko Yamamoto.   

Abstract

A water-soluble cationic porphyrin, 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)-21H,23H-porphyrin (TmPyP4), has been studied extensively because of its unique physicochemical properties that lead to interactions with nucleic acids, as well as its therapeutic application. Formation of a complex between TmPyP4 and parallel G-quadruplex DNA formed from a single repeat sequence of the human telomere, d(TTAGGG), has been characterized in an effort to elucidate the mode of molecular recognition between TmPyP4 and the DNA. The study demonstrated that TmPyP4 intercalates into the A3pG4 step of [d(TTAGGG)]4 with an association constant of 6.2 x 10(6) M(-1) and a stoichiometric ratio of 1:1. The binding of TmPyP4 to the A3pG4 step of [d(TTAGGG)]4 was found to be stabilized by the pi-pi stacking interaction of the porphyrin ring of TmPyP4 with the G4 quartet as well as the A3 bases of the G-quadruplex DNA. These findings provide novel insights for the design of porphyrin derivatives that bind to DNA with high affinity and specificity.

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Year:  2006        PMID: 16734413     DOI: 10.1021/bi052442z

Source DB:  PubMed          Journal:  Biochemistry        ISSN: 0006-2960            Impact factor:   3.162


  10 in total

1.  Potentiation by potassium iodide reveals that the anionic porphyrin TPPS4 is a surprisingly effective photosensitizer for antimicrobial photodynamic inactivation.

Authors:  Liyi Huang; Ahmed El-Hussein; Weijun Xuan; Michael R Hamblin
Journal:  J Photochem Photobiol B       Date:  2017-10-31       Impact factor: 6.252

2.  Structural characterization of a carbon monoxide adduct of a heme-DNA complex.

Authors:  Kaori Saito; Hulin Tai; Masashi Fukaya; Tomokazu Shibata; Ryu Nishimura; Saburo Neya; Yasuhiko Yamamoto
Journal:  J Biol Inorg Chem       Date:  2011-12-28       Impact factor: 3.358

3.  Effect of overall charge and charge distribution on cellular uptake, distribution and phototoxicity of cationic porphyrins in HEp2 cells.

Authors:  Timothy J Jensen; M Graça H Vicente; Raymond Luguya; Jolanna Norton; Frank R Fronczek; Kevin M Smith
Journal:  J Photochem Photobiol B       Date:  2010-05-23       Impact factor: 6.252

4.  Mass spectrometric studies on effects of counter ions of TMPyP4 on binding to human telomeric DNA and RNA G-quadruplexes.

Authors:  Li-Ping Bai; Jie Liu; Li Han; Hing-Man Ho; Renxiao Wang; Zhi-Hong Jiang
Journal:  Anal Bioanal Chem       Date:  2014-06-18       Impact factor: 4.142

5.  Interaction between cationic zinc porphyrin and lead ion induced telomeric guanine quadruplexes: evidence for end-stacking.

Authors:  Jingxi Pan; Suping Zhang
Journal:  J Biol Inorg Chem       Date:  2008-12-02       Impact factor: 3.358

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

Authors:  Sarah E Evans; Miguel A Mendez; Kevin B Turner; Loryn R Keating; Ryan T Grimes; Sarah Melchoir; Veronika A Szalai
Journal:  J Biol Inorg Chem       Date:  2007-09-05       Impact factor: 3.358

7.  Iodine-125 radioprobing of intramolecular quadruplex conformation of human telomeric DNA in the presence of cationic porphyrin TMPyP4.

Authors:  Timur I Gaynutdinov; Ronald D Neumann; Igor G Panyutin
Journal:  Int J Radiat Biol       Date:  2008-12       Impact factor: 2.694

8.  A dual-site simultaneous binding mode in the interaction between parallel-stranded G-quadruplex [d(TGGGGT)]4 and cyanine dye 2,2'-diethyl-9-methyl-selenacarbocyanine bromide.

Authors:  Wei Gai; Qianfan Yang; Junfeng Xiang; Wei Jiang; Qian Li; Hongxia Sun; Aijiao Guan; Qian Shang; Hong Zhang; Yalin Tang
Journal:  Nucleic Acids Res       Date:  2012-12-28       Impact factor: 16.971

9.  Molecular docking based screening of triterpenoids as potential G-quadruplex stabilizing ligands with anti-cancer activity.

Authors:  Sittichai Sillapapongwarakorn; Somchai Yanarojana; Darawan Pinthong; Amnuay Thithapandha; Jiraporn Ungwitayatorn; Porntip Supavilai
Journal:  Bioinformation       Date:  2017-09-30

10.  An exonuclease I hydrolysis assay for evaluating G-quadruplex stabilization by small molecules.

Authors:  Yuan Yao; Quan Wang; Yu-hua Hao; Zheng Tan
Journal:  Nucleic Acids Res       Date:  2007-04-10       Impact factor: 16.971

  10 in total

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