Spermine detection via metal-mediated ethynylarene 'turn-on' fluorescence signaling.

作者: James T. Fletcher , Brent S. Bruck

DOI: 10.1016/J.SNB.2014.10.116

关键词: SpermineChelationStereochemistryBathochromic shiftSpermidineFluorescencePhotochemistryPutrescinePolyamineChemistryCadaverine

摘要: Abstract A dicarboxylated ethynylarene was shown to behave as a fluorescent chemosensor for millimolar concentrations of polyamines when mixed with Cd(II), Pb(II) or Zn(II) ions at micromolar concentrations. bathochromic shift and intensification fluorescence emission observed increasing amounts metal ion in the presence aqueous buffered pH = 7.6. Such perturbations manifested ‘turn-on’ signals from ratiometric comparison intensities 390 nm versus 340 nm. Using mediator, spermine selectively detected 40-fold signal enhancement relative spermidine, putrescine, cadaverine several other non-biogenic diamines. Evaluation additional triamine tetraamine analytes showed influence that amine group quantity spacing had on generation. By ratio ethynylarene, detection limit successfully lowered 25 level. Noncovalent association between polyamine are believed promote spectroscopic changes. This study exploits subtle impact structural identity has transition chelation define new approach toward development.

参考文章(48)
Joseph A. Christensen, James T. Fletcher, 2-(1,2,3-Triazol-4-yl)pyridine-containing ethynylarenes as selective ‘turn-on’ fluorescent chemosensors for Ni(II) Tetrahedron Letters. ,vol. 55, pp. 4612- 4615 ,(2014) , 10.1016/J.TETLET.2014.06.059
Masayuki Takeuchi, Toshihisa Mizuno, Hideyuki Shinmori, Michio Nakashima, Seiji Shinkai, Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe Tetrahedron. ,vol. 52, pp. 1195- 1204 ,(1996) , 10.1016/0040-4020(95)00979-5
K. R. A. Samankumara Sandanayake, Kazuaki Nakashima, Seiji Shinkai, Specific recognition of disaccharides by trans-3,3′-stilbenediboronic acid: Rigidification and fluoresecence enhancement of the stilbene skeleton upon formation of a sugar-stilbene macrocycle Journal of The Chemical Society, Chemical Communications. pp. 1621- 1622 ,(1994) , 10.1039/C39940001621
Sergey A. Malashikhin, Kim K. Baldridge, Nathaniel S. Finney, Efficient discovery of fluorescent chemosensors based on a biarylpyridine scaffold. Organic Letters. ,vol. 12, pp. 940- 943 ,(2010) , 10.1021/OL902902M
Calden N. Carroll, Brian A. Coombs, Sean P. McClintock, Charles A. Johnson II, Orion B. Berryman, Darren W. Johnson, Michael M. Haley, Anion-dependent fluorescence in bis(anilinoethynyl)pyridine derivatives: switchable ON-OFF and OFF-ON responses. Chemical Communications. ,vol. 47, pp. 5539- 5541 ,(2011) , 10.1039/C1CC10947B
James T. Fletcher, Brent S. Bruck, Douglas E. Deever, Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II) Tetrahedron Letters. ,vol. 54, pp. 5366- 5369 ,(2013) , 10.1016/J.TETLET.2013.07.111
Masao Kawakita, Kyoko Hiramatsu, Diacetylated derivatives of spermine and spermidine as novel promising tumor markers. Journal of Biochemistry. ,vol. 139, pp. 315- 322 ,(2006) , 10.1093/JB/MVJ068
N FINNEY, Combinatorial discovery of fluorophores and fluorescent probes. Current Opinion in Chemical Biology. ,vol. 10, pp. 238- 245 ,(2006) , 10.1016/J.CBPA.2006.04.025