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Analytical and Bioanalytical Chemistry

, Volume 406, Issue 26, pp 6723–6733 | Cite as

A new BODIPY-based long-wavelength fluorescent probe for chromatographic analysis of low-molecular-weight thiols

  • Li-Yun Zhang
  • Feng-Qin Tu
  • Xiao-Feng Guo
  • Hong WangEmail author
  • Peng Wang
  • Hua-Shan Zhang
Research Paper

Abstract

A new long-wavelength fluorescent probe, 1,7-dimethyl-3,5-distyryl-8-phenyl-(4′-iodoacetamido)difluoroboradiaza-s-indacene (DMDSPAB-I), was designed and synthesized for thiol labeling in high-performance liquid chromatography (HPLC). The excitation and emission wavelengths of DMDSPAB-I are 620 and 630 nm, respectively, with a high fluorescence quantum yield of 0.557, which is advantageous in preventing interference of intrinsic fluorescence from complex biological matrices and enabling high sensitivity HPLC. Based on DMDSPAB-I, a reversed-phase HPLC method was developed for measuring low-molecular-weight thiols including glutathione, cysteine, homocysteine, N-acetylcysteine, cysteinylglycine, and penicillamine. After the specific reaction of DMDSPAB-I with thiols, baseline separation of all six stable derivatives was achieved through isocratic elution on a C18 column within 25 min, with the limits of detection (signal-to-noise ratio = 3) from 0.24 nmol L−1 for glutathione to 0.72 nmol L−1 for penicillamine. The proposed method was validated in part by measuring thiols in blood samples from mice, with recoveries of 95.3–104.3 %.

Keywords

1,7-Dimethyl-3,5-distyryl-8-phenyl-(4′-iodoacetamido)difluoroboradiaza-s-indacene Thiols long-wavelength Fluorescence detection High-performance liquid chromatography 

Notes

Acknowledgement

This work was supported by the National Natural Science Foundation of China (No. 20835004, 31170344 and 21105074, Beijing, China) and the Research Projects of General Administration of Quality Supervision, Inspection and Quarantine of China (No. 2013IK159).

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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Li-Yun Zhang
    • 1
  • Feng-Qin Tu
    • 1
  • Xiao-Feng Guo
    • 1
  • Hong Wang
    • 1
    Email author
  • Peng Wang
    • 2
  • Hua-Shan Zhang
    • 1
  1. 1.Key Laboratory of Analytical Chemistry for Biology and Medicine (Ministry of Education), College of Chemistry and Molecular SciencesWuhan UniversityWuhanChina
  2. 2.Technology CenterHubei Entry-Exit Inspection and Quarantine BureauWuhanChina

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