Volume 9, Issue 3 (2018)                   JMBS 2018, 9(3): 395-402 | Back to browse issues page

XML Persian Abstract Print


Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:

Hassani L, Safaei E, Hakimian F, Soufian S. Thermodynamic Investigation of Copper Porphyrazines and Phthalocyanine Interaction with Human Telomeric G-Quadruplex DNA. JMBS 2018; 9 (3) :395-402
URL: http://biot.modares.ac.ir/article-22-13905-en.html
1- Biological Sciences Faculty, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, Iran
2- Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iran
3- Biology Department, Basic Sciences Faculty, Arak Branch, Payam-e-Noor University, Arak, Iran, Biology Department, Arak Branch, Payam-e-Noor University, Ring Road, Elahie, Arak, Iran. Postal Code: 3818889581 , s_soofian@pnu.ac.ir
Abstract:   (4553 Views)
Aims: The G-quadruplex structural motifs of DNA are considered a novel target for drug discovery. As potential compounds, small molecules that selectively target the G-quadruplex structures may be used for therapeutic purposes. The aim of this study was the thermodynamic investigation of copper porphyrazines and phthalocyanine interaction with human telomeric G-quadruplex DNA.
Materials and Methods: In the present experimental study, interaction of an anionic water-soluble phthalocyanine Cu(PcTs) and two cationic water-soluble tetrapyridinoporphyrazines, including [Cu(2,3-tmtppa)] 4+ and [Cu(3,4-tmtppa)]4+ complexes with human telomeric G-quadruplex DNA was thermodynamically investigated in different concentrations of Na+ and K+ cations, using fluorescence spectroscopy. The data were analyzed via the Stern-Volmer plot and the van't Hoff plot.
Findings: Fluorescent intercalator displacement indicated the displacement ability of the complexes with thiazole orange. Stern-Volmer plots of the porphyrazines exhibited a slight positive deviation from a straight line, suggesting both static and dynamic quenching. In addition, the quenching effect of the two porphyrazines was noticeably higher than the phthalocyanine, implying binding of Cu(PcTs) to both forms of the quadruplex was weaker compared to Cu(2,3-tmtppa) and Cu(3,4-tmtppa). Gibbs free energy (∆G) for binding was negative, implying that the interaction between the complexes and the G-quadruplex DNA was favorable thermodynamically.
Conclusion: The binding of copper porphyrazines to G-quadruplex DNA is stronger than copper phthalocyanine, and their binding is favorable thermodynamically. Porphyrazines have potential to be used as anti-cancer compounds and are suitable complexes for pharmaceutical studies.
Full-Text [PDF 679 kb]   (2943 Downloads)    
Article Type: Original Manuscript | Subject: Agricultural Biotechnology
Received: 2016/07/19 | Accepted: 2017/08/20 | Published: 2018/09/22

References
1. Parish JH. Principles of nucleic acid structure. Biochem Educ. 1985;13(2):92. [Link] [DOI:10.1016/0307-4412(85)90046-9]
2. Huppert JL. Four-stranded nucleic acids: Structure, function and targeting of G-quadruplexes. Chem Soc Rev. 2008;37(7):1375-84. [Link] [DOI:10.1039/b702491f]
3. Sannohe Y, Sugiyama H. Overview of formation of G-quadruplex structures. Curr Protoc. 2010;40(1):17.2.1-17. [Link]
4. Patel DJ, Phan, AT, Kuryavyi V. Human telomere, oncogenic promoter and 5'-UTR G-quadruplexes: Diverse higher order DNA and RNA targets for cancer therapeutics. Nucleic Acids Res. 2007;35(22):7429-55. [Link] [DOI:10.1093/nar/gkm711]
5. Kumar RS, Arunachalam S, Periasamy VS, Preethy CP, Riyasdeen A, Akbarsha MA. DNA binding and biological studies of some novel water-soluble polymer-copper(II)-phenanthroline complexes. Eur J Med Chem. 2008;43(10):2082-91. [Link] [DOI:10.1016/j.ejmech.2007.09.017]
6. Chen SM, Chen SV. The interaction of water-soluble iron porphyrins with DNA films and the electrocatalytic properties for inorganic and organic nitro compounds. Electrochimica Acta. 2003;48(27):4049-60. [Link] [DOI:10.1016/S0013-4686(03)00562-0]
7. Oganesian L, Bryan TM. Physiological relevance of telomeric G-quadruplex formation: A potential drug target. Bioessays. 2007;29(2):155-65. [Link] [DOI:10.1002/bies.20523]
8. Rothemund P. Formation of porphyrins from pyrrole and aldehydes. J Am Chem Soc. 1935;57(10):2010-1. [Link] [DOI:10.1021/ja01313a510]
9. Rothemund P. A new porphyrin synthesis, the synthesis of porphin. J Am Chem Soc. 1936;58(4):625-7. [Link] [DOI:10.1021/ja01295a027]
10. Asadi M, Safaei E, Ranjbar B, Hasani L. A study on the binding of two water-soluble tetrapyridinoporphyrazinato copper(II) complexes to DNA. J Mol Struct. 2005;754(1-3):116-23. [Link] [DOI:10.1016/j.molstruc.2005.06.033]
11. Hassani L, Hakimian F, Safaei E. Spectroscopic investigation on the interaction of copper porphyrazines and phthalocyanine with human telomeric G-quadruplex DNA. Biophys Chem. 2014;187-188:7-13. [Link] [DOI:10.1016/j.bpc.2013.11.009]
12. Garbett NC, Chaires JB. Binding: A polemic and rough guide. Methods Cell Boil. 2008;84:3-23. [Link] [DOI:10.1016/S0091-679X(07)84001-5]
13. Monchaud D, Allain C, Teulade-Fichou MP. Development of a fluorescent intercalator displacement assay (G4-FID) for establishing quadruplex-DNA affinity and selectivity of putative ligands. Bioorg Med Chem Lett. 2006;16(18):4842-5. [Link] [DOI:10.1016/j.bmcl.2006.06.067]
14. Tran PL, Largy E, Hamon F, Teulade-Fichou MP, Mergny JL. Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures. Biochimie. 2011;93(8):1288-96. [Link] [DOI:10.1016/j.biochi.2011.05.011]
15. Nakayama S, Kelsey I, Wang J, Roelofs K, Stefane B, Luo Y, et al. Thiazole orange-induced c-di-GMP quadruplex formation facilitates a simple fluorescent detection of this ubiquitous biofilm regulating molecule. J Am Chem Soc. 2011;133(13):4856-64. [Link] [DOI:10.1021/ja1091062]
16. Eftink MR, Ghiron CA. Exposure of tryptophanyl residues in proteins, quantitative determination by fluorescence quenching studies. Biochemistry. 1976;15(3):672-80. [Link] [DOI:10.1021/bi00648a035]
17. Bushueva TL, Busel EP, Burstein EA. Some regularities of dynamic accessibility of buried fluorescent residues to external quenchers in proteins. Arch Biochem Biophys. 1980;204(1):161-6. [Link] [DOI:10.1016/0003-9861(80)90019-3]
18. Gray RD, Pettracone L, Buscaglia R, Chaires JB. 2-Aminopurine as a probe for Quadruplex loop structures. Methods Mol Biol. 2010;608:121-36. [Link] [DOI:10.1007/978-1-59745-363-9_8]
19. Ren J, Chaires JB. Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry. 1999;38(49):16067-75. [Link] [DOI:10.1021/bi992070s]
20. Asadi M, Safaei E, Ranjbar B, Hasani L. Thermodynamic and spectroscopic study on the binding of cationic Zn(II) and Co(II) tetrapyridinoporphyrazines to calf thymus DNA: The role of the central metal in binding parameters. New J Chem. 2004;28(10):1227-34. [Link] [DOI:10.1039/b404068f]
21. Olsen CM. Thermodynamic characterization of the folding and interactions of G-quadruplexes [Dissertation]. Omaha: University of Nebraska Medical Center; 2008. [Link]
22. Neidle S, Balasubramanian S, editors. Quadruplex nucleic acids. London: Royal Society of Chemistry; 2006. [Link] [DOI:10.1039/9781847555298]
23. Xiao JB, Chen XQ, Jiang XY, Hilczer M, Tachiya M. Probing the interaction of trans-resveratrol with bovine serum albumin: A fluorescence quenching study with Tachiya model. J Fluoresc. 2008;18(3-4):671-8. [Link] [DOI:10.1007/s10895-008-0346-x]
24. Zhang G, Hu X, Fu P. Spectroscopic studies on the interaction between carbaryl and calf thymus DNA with the use of ethidium bromide as a fluorescence probe. J Photochem Photobiol B. 2012;108:53-61. [Link] [DOI:10.1016/j.jphotobiol.2011.12.011]
25. Zhang Y, Wang X, Ding L. Interaction between tryptophan-vanillin Schiff base and herring sperm DNA. J Serb Chem Soc. 2010;75(9):1191-201. [Link] [DOI:10.2298/JSC100128107Z]
26. Gonçalves DP, Rodriguez R, Balasubramanian S, Sanders JK. Tetramethylpyridiniumporphyrazines--a new class of G-quadruplex inducing and stabilising ligands. Chem Commun (Camb). 2006;(45):4685-7. [Link] [DOI:10.1039/B611731G]

Add your comments about this article : Your username or Email:
CAPTCHA

Send email to the article author


Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.