Selective FL Quenching or Enhancing of Diimine Ligands by Guanine

Overview

Journal J Fluoresc

Specialties Biophysics
Chemistry

Date 2013 Apr 26

PMID 23615929

Authors

Srung Smanmoo

Shinya Kawasaki

Pramuan Tangboriboonrat

Takayuki Shibata

Tsutomu Kabashima

Masaaki Kai

Affiliations

Soon will be listed here.

Abstract

Diimine ligand (DL) 1 significantly exhibited the fluorescence quenching upon binding to guanine. Changing at the para-substituent of the phenyl ring from the hydroxyl to bromo groups reversely enhanced the fluorescence in the presence of guanine. The reverse in the fluorescence selectivity indicated the profound effect of the substituent at the para-position of the phenyl ring. The simple synthesis of DL 1 and DL 2 with good selectivity for guanine offers these DLs as promising compounds for chemosensors of other guanine derivatives.

References

Seo H, Karim M, Lee S . Selective fluorimetric recognition of cesium ion by 15-crown-5-anthracene. J Fluoresc. 2008; 18(5):853-7. DOI: 10.1007/s10895-008-0314-5. View

Gellman S . Introduction: Molecular Recognition. Chem Rev. 1997; 97(5):1231-1232. DOI: 10.1021/cr970328j. View

Goswami P, Das D . N,N,N,N-tetradentate macrocyclic ligand based selective fluorescent sensor for zinc (II). J Fluoresc. 2012; 22(4):1081-5. DOI: 10.1007/s10895-012-1046-0. View

Shirai M, Murakami H, Tsunooka M . Cation-sensitive fluorescence of anionic polymers bearing naphtho-18-crown-6 units. J Fluoresc. 2013; 6(4):237-43. DOI: 10.1007/BF00732827. View

Wang H, Yang R, Yang L, Tan W . Nucleic acid conjugated nanomaterials for enhanced molecular recognition. ACS Nano. 2009; 3(9):2451-60. PMC: 2765789. DOI: 10.1021/nn9006303. View

Seo H, Lee S . A novel fluorescent cesium ion-selective optode membrane based on 15-crown-5-anthracene. J Fluoresc. 2010; 21(2):747-51. DOI: 10.1007/s10895-010-0765-3. View

Cui Q, Ma K, Shao Y, Xu S, Wu F, Liu G . Gap site-specific rapid formation of fluorescent silver nanoclusters for label-free DNA nucleobase recognition. Anal Chim Acta. 2012; 724:86-91. DOI: 10.1016/j.aca.2012.02.044. View

Kuhn K, Dyke J . A renewable-reagent fiber-optic sensor for measurement of high acidities. Anal Chem. 2011; 68(17):2890-6. DOI: 10.1021/ac960242a. View

Nasomphan W, Tangboriboonrat P, Smanmoo S . Selective fluorescence sensing of deoxycytidine 5'-monophosphate (dCMP) employing a bis(diphenylphosphate)diimine ligand. J Fluoresc. 2010; 21(1):187-94. DOI: 10.1007/s10895-010-0703-4. View

10.

Idzik K, Cywinski P, Cranfield C, Mohr G, Beckert R . Molecular recognition of the antiretroviral drug abacavir: towards the development of a novel carbazole-based fluorosensor. J Fluoresc. 2011; 21(3):1195-204. PMC: 3120969. DOI: 10.1007/s10895-010-0798-7. View

11.

Martinez-Manez R, Sancenon F . New advances in fluorogenic anion chemosensors. J Fluoresc. 2005; 15(3):267-85. DOI: 10.1007/s10895-005-2626-z. View

12.

He Y, Wang Y, Tang L, Liu H, Chen W, Zheng Z . Binding of puerarin to human serum albumin: a spectroscopic analysis and molecular docking. J Fluoresc. 2007; 18(2):433-42. DOI: 10.1007/s10895-007-0283-0. View

13.

Knox J, Pratt R . Different modes of vancomycin and D-alanyl-D-alanine peptidase binding to cell wall peptide and a possible role for the vancomycin resistance protein. Antimicrob Agents Chemother. 1990; 34(7):1342-7. PMC: 175978. DOI: 10.1128/AAC.34.7.1342. View

14.

Xu S, Mutharasan R . Cell viability measurement using 2',7'-bis-(2-carboxyethyl)-5-(and-6)-carboxyfluorescein acetoxymethyl ester and a cantilever sensor. Anal Chem. 2011; 83(4):1480-3. DOI: 10.1021/ac102757q. View

15.

Kienberger F, Ebner A, Gruber H, Hinterdorfer P . Molecular recognition imaging and force spectroscopy of single biomolecules. Acc Chem Res. 2006; 39(1):29-36. DOI: 10.1021/ar050084m. View