An environmentally sensitive molecular rotor as a NIR fluorescent probe for the detection of islet amyloid polypeptide

Pin Han Lin, Chang Shun Tsai, Chia Chien Hsu, I. Ren Lee, Yu Xin Shen, Hsiu Fang Fan, Yun Wen Chen, Ling Hsien Tu, Wei Min Liu

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


The deposits of human islet amyloid polypeptide (IAPP), also called amylin, in the pancreas have been postulated to be a factor of pancreatic β-cell dysfunction and is one of the common pathological hallmarks of type II diabetes mellitus (T2DM). Therefore, it is imperative to gain an in-depth understanding of the formation of these aggregates. In this study, we demonstrate a rationally-designed strategy of an environmentally sensitive near-infrared (NIR) molecular rotor utilizing thioflavin T (ThT) as a scaffold for IAPP deposits. We extended the π delocalized system not only to improve the viscosity sensitivity but also to prolong the emission wavelength to the NIR region. A naphthalene moiety was also introduced to adjust the sensitivity of our designed probes to differentiate the binding microenvironment polarity of different targeted proteins. As a result, a novel NIR fluorogenic probe toward IAPP aggregates, namely AmySP-4-Nap-Ene, was first developed. When attached to different protein aggregates, this probe exhibited distinct fluorescence emission profiles. In a comparison with ThT, the fluorescence emission of non-ionic AmySP-4-Nap-Ene exhibits a significant difference between the presence of non-fibrillar and fibrillar IAPP and displays a higher binding affinity toward IAPP fibrils. Further, the AmySP-4-Nap-Ene can be utilized to monitor IAPP accumulating process and image fibrils both in vitro and in living cells.

Original languageEnglish
Article number124130
Publication statusPublished - 2023 Mar 1

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry


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