A fluorescent chemoprobe based on 1,8-naphthalimide derivative specific for cellular recognition of cysteine over homocysteine and glutathione

Aydin D., Arslan F. N., Elmas Ş. N., Bostanci A., Geyik G. A., Savran T., ...Daha Fazla

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, cilt.433, 2022 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 433
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.jphotochem.2022.114119
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Anahtar Kelimeler: Biothiols, Cysteine, DFT, Fluorescent sensor, Living cell, TURN-ON PROBE, LIVING CELLS, THIOLS, BODIPY, SENSOR
  • İstanbul Üniversitesi-Cerrahpaşa Adresli: Evet

Özet

Development of highly selective, sensitive and low-cost fluorescence probes for the specific recognition of cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH) is of considerable importance. Herein, a new fluorescence chemoprobe 4-cyano-[1,1-biphenyl]-4-yl propiolate appended N-butyl-1,8-naphthalimide (BUNB) for the specific recognition of Cys for cellular recognition was synthesized. BUNB exhibited an excellent selectivity with a low detection limit (0.24 mu M) for Cys over GSH and Hcy. The validation study was also performed using the appropriate analytical parameters and statistical tests. The thiol-propiolate cyclization/addition sequence phenomenon of the binding between BUNB and Cys was verified using MALDI TOF-MS, emission spectra and DFT computation. Moreover, the fluorescence imaging study in living-cells was carried out and the results indicated that BUNB could be successfully used for monitoring Cys in both healthy (normal human hepatocytes, THLE2) and cancerous (hepatocellular carcinoma, HepG2) cells.