A BODIPY-based probe for amyloid-β imaging in vivo

Mingguang Zhu, Guoyang Zhang, Ziwei Hu, Chaofeng Zhu, Yixiang Chen, Tony D. James, Lijun Ma, Zhuo Wang

Research output: Contribution to journalArticlepeer-review

5 Citations (SciVal)

Abstract

Alzheimer's disease (AD) is a neurodegenerative disease, and the efficient detection of amyloid-β (Aβ) plaques can greatly enhance diagnosis and therapy. Most reported probes used to detect Aβ are based on the N,N-dimethylamino group. As such, the design of new Aβ-recognition units facilitates the recognition of Aβ. Herein, we present an Aβ recognition unit [4-(Boc-amino) benzene] used to develop BocBDP. BocBDP can recognize and image Aβ plaques both in vitro and in vivo through the interaction with amino acid residues Lys16 (K16), Val18 (V18), and Glu22 (E22). The hydrogen bonding interaction (1.9 Å) between the carbonyl oxygen atom in the Boc unit and the amino acid residue K16 allows BocBDP to bind strongly to Aβ, resulting in a five-fold fluorescence enhancement and a high affinity (Kd = 67.8 ± 3.18 nM). BocBDP can cross the BBB and image Aβ for at least 2 hours. We anticipate that our Aβ recognition unit will help improve the design of probes that specifically recognize Aβ.

Original languageEnglish
Pages (from-to)1903-1909
Number of pages7
JournalOrganic Chemistry Frontiers
Volume10
Issue number8
Early online date10 Mar 2023
DOIs
Publication statusPublished - 10 Mar 2023

Bibliographical note

Funding Information:
We are thankful for the support from the Beijing Natural Science Foundation (No. 7232342), the Natural Science Foundation of China (No. 82131430174 and 81961138011), the Academy of Medical Sciences Newton Advanced Fellowship (NAFR13\1015), the National Key Research and Development Program of China (2021YFC2101500), and the China Scholarship Council. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01).

ASJC Scopus subject areas

  • Organic Chemistry

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