ARTICLE

A Turn-ON Near-Infrared Fluorescent Probe for the Detection of Dipeptidyl Peptidase IV Activity in Liver Cancers

  • Fei Zhang ,
  • Yu Mei ,
  • Xuefeng Ding ,
  • Zaifeng Li ,
  • Peng Zhang ,
  • Caifeng Ding
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  • Key Laboratory of Analytical Chemistry for Life Science in Universities of Shandong, Shandong Key Laboratory of Biochemical Analysis, Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science (Ministry of Education), College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042

Received date: 2024-04-19

  Revised date: 2024-05-20

  Online published: 2024-06-13

Supported by

National Natural Science Foundation of China(21904077); National Natural Science Foundation of China(22074074); Youth Innovation Team Development Program of Shandong Higher Education Institutions(2022KJC004); Taishan Scholar Program of Shandong Province(tstp20231227); Natural Science Foundation of Qingdao City(23-2-1-175-zyyd-jch)

Abstract

Dipeptidyl peptidase IV (DPP-IV), a transmembrane glycoprotein overexpressed in cancer cells, is often used as an important biomarker for early detection of tumors. A near-infrared turn ON fluorescence probe (MB-DPP) was developed for the sensitively detection of DPP-IV in liver cancer cells. MB-DPP employs methylene blue as fluorophore and p-aminobenzyl alcohol as the connecting arm to bond glycyl-L-proline as the specific cleavage site of DPP-IV through dehydration condensation reaction, thereby achieving the fluorescence “turn on” reaction triggered by DPP-IV. Probe MB-DPP emits strong near-infrared fluorescence at 691 nm after the incubation with DPP-IV. Spectral experiments showed that MB-DPP exhibited high selectivity and detection sensitivity (with a detection limit of 1.12 ng/mL) for DPP-VI. Bio-imaging studies showed that MB-DPP could not only achieve fluorescence imaging analysis of DPP-IV activity in liver cancer cells, but also be used for imaging of DPP-IV in liver cancer tumors. Therefore, the development of probe MB-DPP will contribute to the early diagnosis of liver cancer.

Cite this article

Fei Zhang , Yu Mei , Xuefeng Ding , Zaifeng Li , Peng Zhang , Caifeng Ding . A Turn-ON Near-Infrared Fluorescent Probe for the Detection of Dipeptidyl Peptidase IV Activity in Liver Cancers[J]. Chinese Journal of Organic Chemistry, 2024 , 44(11) : 3417 -3426 . DOI: 10.6023/cjoc202404028

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