A cysteine-selective fluorescent probe for the cellular detection of cysteine

Hyo Sung Jung, Ji Hye Han, Tuhin Pradhan, Sooyeon Kim, Seok Won Lee, Jonathan L. Sessler, Tae Woo Kim, Chulhun Kang, Jong Seung Kim

Research output: Contribution to journalArticle

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Abstract

A series of coumarin fluorophores (1-3), each bearing a double bond conjugated quinoline unit that can undergo a Michael-type reaction with thiol-containing compounds, is reported. These systems, designed to provide so-called turn-on changes in fluorescence response when exposed to thiols, act as fluorescent chemical sensors for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). In the case of 1, selectivity for Cys over Hcy and GSH is observed, both in terms of analyte-induced signal enhancement and response time. On the basis of fluorescence spectroscopic analyses, DFT calculations, and pH dependent studies this substrate selectivity is ascribed to steric interactions between the substituents on the quinolone units present in 1 and the targeted thiols, as well as to the comparatively lower pK a value of Cys relative to Hcy and GSH. In aqueous solution, probe 1 was found capable of detecting Cys with a detection limit of 10 -7 m. This system was successfully applied to the fluorescence imaging of intracellular Cys in HepG2 cells.

Original languageEnglish
Pages (from-to)945-953
Number of pages9
JournalBiomaterials
Volume33
Issue number3
DOIs
Publication statusPublished - 2012 Jan 1

Fingerprint

Fluorescent Dyes
Cysteine
Fluorescence
Homocysteine
Sulfhydryl Compounds
Bearings (structural)
Fluorophores
Chemical sensors
Discrete Fourier transforms
Optical Imaging
Quinolones
Hep G2 Cells
Imaging techniques
Reaction Time
Glutathione
Substrates
Limit of Detection

Keywords

  • Cellular detection
  • Cysteine
  • DFT calculations
  • Fluorescence
  • Thiol

ASJC Scopus subject areas

  • Biomaterials
  • Bioengineering
  • Ceramics and Composites
  • Mechanics of Materials
  • Biophysics

Cite this

A cysteine-selective fluorescent probe for the cellular detection of cysteine. / Jung, Hyo Sung; Han, Ji Hye; Pradhan, Tuhin; Kim, Sooyeon; Lee, Seok Won; Sessler, Jonathan L.; Kim, Tae Woo; Kang, Chulhun; Kim, Jong Seung.

In: Biomaterials, Vol. 33, No. 3, 01.01.2012, p. 945-953.

Research output: Contribution to journalArticle

Jung, HS, Han, JH, Pradhan, T, Kim, S, Lee, SW, Sessler, JL, Kim, TW, Kang, C & Kim, JS 2012, 'A cysteine-selective fluorescent probe for the cellular detection of cysteine', Biomaterials, vol. 33, no. 3, pp. 945-953. https://doi.org/10.1016/j.biomaterials.2011.10.040
Jung, Hyo Sung ; Han, Ji Hye ; Pradhan, Tuhin ; Kim, Sooyeon ; Lee, Seok Won ; Sessler, Jonathan L. ; Kim, Tae Woo ; Kang, Chulhun ; Kim, Jong Seung. / A cysteine-selective fluorescent probe for the cellular detection of cysteine. In: Biomaterials. 2012 ; Vol. 33, No. 3. pp. 945-953.
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