A new cationic porphyrin derivative (TMPipEOPP) with large side arm substituents: A highly selective G-quadruplex optical probe

PLoS ONE

Volumn 7, Issue 5, 2012, Pages

  Zhu, Li Na ^a   Zhao, Shu Juan ^a   Wu, Bin ^a   Li, Xiao Zeng ^a   Kong, De Ming ^b  

^a TIANJIN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

5,10,15,20 TETRA [4 [2 (1 METHYL 1 PIPERIDINYL)ETHOXY]PHENYL]PORPHYRIN; DOUBLE STRANDED DNA; GUANINE QUADRUPLEX; PORPHYRIN DERIVATIVE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DNA STRUCTURE; FLUORESCENCE SPECTROSCOPY; MOLECULAR RECOGNITION; PROTEIN DNA INTERACTION; SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET VISIBLE ABSORPTION SPECTROSCOPY;

DNA, SINGLE-STRANDED; G-QUADRUPLEXES; PIPERIDINES; PORPHYRINS;

TETRA;

EID: 84861303012     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0035586     Document Type: Article

References (39)

1. Huppert JL, (2008) Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes. Chem Soc Rev 37: 1375-1384.
2. Patel DJ, Phan AT, Kuryavyi V, (2007) Human telomere, oncogenic promoter and 5′-UTR G-quadruplexes: diverse higher order DNA and RNA targets for cancer therapeutics. Nucleic Acids Res 35: 7429-7455.
3. Balasubramanian S, Hurley LH, Neidle S, (2011) Targeting G-quadruplexes in gene promoters: a novel anticancer strategy? Nat Rev Drug Discov 10: 261-275.
4. Tran PLT, Mergny J-L, Alberti P, (2010) Stability of telomeric G-quadruplexes. Nucleic Acids Res 39: 3282-3294.
5. Murat P, Singh Y, Defranoq E, (2011) Methods for investigating G-quadruplex DNA/ligand interactions. Chem Soc Rev 40: 5293-5307.
6. Balasubramanian S, Neidle S, (2009) G-quadruplex nucleic acids as therapeutic targets. Curr Opin Chem Biol 13: 345-353.
7. Lane AN, Chaires JB, Gray RD, Trent JO, (2008) Stability and kinetics of G-quadruplex structures. Nucleic Acids Res 36: 5484-5515.
8. Lu Y-J, Yan S-C, Chan F-Y, Zou L, Chung W-H, et al. (2011) Benzothiazole-substituted benzofuroquinolinium dye: a selective switch-on fluorescent probe for G-quadurplex. Chem Commun 47: 4971-4973.
9. Alzeer J, Vummidi BR, Roth PJC, Luedtke NW, (2009) Guanidinium-modified phthalocyanines as high-affinity G-quadruplex fluorescent probes and transcriptional regulators. Angew Chem Int Ed 48: 9362-9365.
10. Romera C, Bombarde O, Bonnet R, Gomez D, Dumy P, et al. (2011) Improvement of porphyrins for G-quadruplex DNA targeting. Biochimie 93: 1310-1317.
11. Bhasikuttan AC, Mohanty J, Pal H, (2007) Interaction of malachite green with guanine-rich single-stranded DNA: preferential binding to a G-quadruplex. Angew Chem Int Ed 46: 9305-9307.
12. Kong D-M, Ma Y-E, Wu J, Shen H-X, (2009) Discrimination of G-quadruplexes from duplex and single-stranded DNAs with fluorescence and energy-transfer fluorescence spectra of crystal violet. Chem Eur J 15: 901-909.
13. Teulade-Fichou M-P, Carrasco C, Guittat L, Bailly C, Alberti P, et al. (2003) Selective recognition of G-quadruplex telomeric DNA by a bis(quinacridine) macrocycle. J Am Chem Soc 125: 4732-4740.
14. Yang P, De Cian A, Teulade-Fichou M-P, Mergny J-L, Monchaud D, (2009) Engineering bisquinolinium/thiazole orange conjugates for fluorescent sensing of G-quadruplex DNA. Angew Chem Int Ed 48: 2188-2191.
15. Arthanari H, Basu S, Kawano TL, Bolton PH, (1998) Fluorescent dyes specific for quadruplex DNA. Nucleic Acids Res 26: 3724-3728.
16. Guo J-H, Zhu L-N, Kong D-M, Shen H-X, (2009) Triphenylmethane dyes as fluorescent probes for G-quadruplex recognition. Talanta 80: 607-613.
17. Lombardo CM, Martínez IS, Haider S, Gabelica V, De Pauw E, et al. (2010) Structure-based design of selective high-affinity telomeric quadruplex-binding ligands. Chem Commun 46: 9116-9118.
18. Nielsen MC, Ulven T, (2010) Macrocyclic G-quadruplex ligands. Curr Med Chem 17: 3438-3448.
19. Yamashita T, Uno T, Ishikawa Y, (2005) Stabilization of guanine quadruplex DNA by the binding of porphyrins with cationic side arms. Bioorg Med Chem 13: 2423-2430.
20. Wheelhousr RT, Sun D, Han H, Han FX, Hurley LH, (1998) Cationic porphyrins as telomerase inhibitors: the interaction of Tetr-(N-methyl-4-pyridyl)porphine with G-quadruplex DNA. J Am Chem Soc 120: 3261-3262.
21. Martino L, Pagano B, Fotticchia I, Neidle S, Giancola C, (2009) Shedding light on the interaction between TMPyP4 and human telomeric quadruplexes. J Phys Chem B 113: 14779-14786.
22. Wei C, Wang L, Jia G, Zhou J, Han G, et al. (2009) The binding mode of porphyrins with cation side arms to (TG4T)4 G-quadruplex: spectroscopic evidence. Biophys Chem 143: 79-84.
23. Wei C, Jia G, Yuan J, Feng Z, Li C, (2006) A spectroscopic study on the interactions of porphyrin with G-quadruplex DNAs. Biochemistry 45: 6681-6691.
24. Ren J, Chaires JB, (1999) Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry 38: 16067-16075.
25. Dixon IM, Lopez F, Esteve JP, Tejera AM, Blasco MA, et al. (2005) Porphyrin derivatives for telomere binding and telomerase inhibition. Chembiochem 6: 123-132.
26. Dixon IM, Lopez F, Tejera AM, Estève J-P, Blasco MA, et al. (2007) A G-quadruplex ligand with 1000-fold selectivity over duplex DNA. J Am Chem Soc 119: 1502-1503.
27. Bennett M, Krah A, Wien F, Garman E, McKenna R, et al. (2000) A DNA-porphyrin minor-groove complex at atomic resolution: the structural consequence of porphyrin ruffling. Proc Natl Acad Sci U S A 97: 9476-9481.
28. Vialas C, Pratviel G, Meunier B, (2000) Oxidative damage generated by an oxo-metalloporphyrin onto the human telomeric sequence. Biochemistry 39: 9514-9522.
29. Pan J, Zhang S, (2009) Interaction between cationic zinc porphyrin and lead ion induced telomeric guanine quadruplexes: evidence for end-stacking. J Biol Inorg Chem 14: 401-407.
30. Pasternack RF, Gibbs EJ, Villafranca JJ, (1983) Interactions of porphyrins with nucleci acids. Biochemsitry 22: 2406-2414.
31. Wei C, Wang J, Zhang M, (2010) Sepctroscopic study on the binding of porphyrins to (G4T4G4)4 parallel G-quadruplex. Biophys Chem 148: 51-55.
32. Wei C, Jia G, Zhou J, Han G, Li C, (2009) Evidence for the binding mode of porphyrins to G-quadruplex DNA. Phys Chem Chem Phys 11: 4025-4032.
33. Leopoldo M, Lacivita E, Berardi F, Perrone R, (2009) Developments in fluorescent probes for receptor research. Drug Discov Today 14: 706-712.
34. Yu H-Q, Miyoshi D, Sugimoto N, (2006) Characterization of structure and stability of long telomeric DNA G-quadruplexes. J Am Chem Soc 128: 15461-15468.
35. Shinohara K-i, Sannohe Y, Kaieda S, Tanaka K-i, Osuga H, et al. (2010) A chiral wedge molecule inhibits telomerase activity. J Am Chem Soc 132: 3778-3782.
36. Cummaro A, Fottichia I, Franceschin M, Giancola C, Petraccone L, (2011) Binding properties of human telomeric quadruplex multimers: a new route for drug design. Biochimie 93: 1392-1400.
37. Madison WI, SMART (control) and SAINT (integration) software, Bruker Analytical X-ray Systems (1994).
38. Sheldrick GM, (1997) SHELXS-97, A program for the solution of crystal structures from X-ray data, University of Göttingen, Germany.
39. Sheldrick GM, (1997) SHELXL-97, A program for the refinement of crystal structures from X-ray data, University of Göttingen, Germany.