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

doi:10.6023/cjoc202404028

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ARTICLE

激活型近红外荧光探针用于肝癌中二肽基肽酶活性检测

张飞, 梅煜, 丁雪峰, 李再峰^*, 张鹏^*, 丁彩凤^*

光电传感与生命分析教育部重点实验室, 山东省生化分析重点实验室, 山东省生命分析高校重点实验室, 青岛科技大学化学与分子工程学院青岛 266042

收稿日期:2024-04-19 修回日期:2024-05-20
基金资助:
国家自认科学基金(Nos. 21904077, 22074074), 山东省高校优秀青年创新团队项目(2022KJC004), 山东省泰山学者计划(No. tstp20231227)和青岛市自然科学基金(No. 23-2-1-175-zyyd-jch)资助项目.

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^*

Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE; Shandong Key Laboratory of Biochemical Analysis; Key Laboratory of Analytical Chemistry for Life Science in Universities of Shandong; College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042

Received:2024-04-19 Revised:2024-05-20
Contact: *E-mail: lizfengphd@126.com; pengzhang@qust.edu.cn; dingcaifeng@qust.edu.cn
Supported by:
National Natural Science Foundation of China (Nos. 21904077, 22074074), and Youth Innovation Team Development Program of Shandong Higher Education Institutions (No. 2022KJC004), and the Taishan Scholar Program of Shandong Province (No. tstp20231227), and Natural Science Foundation of Qingdao (No. 23-2-1-175-zyyd-jch).

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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. In this work, 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.

Key words: dipeptidyl peptidase, near infrared fluorescent probe, methylene blue, liver cancer, living cell imaging, in vivo imaging

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, doi: 10.6023/cjoc202404028.

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激活型近红外荧光探针用于肝癌中二肽基肽酶活性检测

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

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