A Facile Structural Isomerization-Induced 3D Spatial D-A Interlocked Network for Achieving NIR-II Phototheranostic Agents

Lina Feng; Chunbin Li; Lingxiu Liu; Xin Chen; Guoyu Jiang; Jianguo Wang; Ben Zhong Tang

doi:10.1002/anie.202212673

A Facile Structural Isomerization-Induced 3D Spatial D-A Interlocked Network for Achieving NIR-II Phototheranostic Agents

Angew Chem Int Ed Engl. 2022 Dec 12;61(50):e202212673. doi: 10.1002/anie.202212673. Epub 2022 Nov 15.

Authors

Lina Feng¹, Chunbin Li¹, Lingxiu Liu¹, Xin Chen¹, Guoyu Jiang¹, Jianguo Wang¹, Ben Zhong Tang²

Affiliations

¹ College of Chemistry and Chemical Engineering, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Inner Mongolia University, Hohhot, 010021, P. R. China.
² Shenzhen Institute of Molecular Aggregate Science and Engineering, School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Shenzhen, 518172, P. R. China.

PMID: 36256574
DOI: 10.1002/anie.202212673

Abstract

The performances of second near-infrared (NIR-II) organic phototheranostic agents (OPTAs) depend on both molecular structure and molecular packing when used as nanoparticles (NPs). Herein, we proposed a facile structural isomerization-induced 3D spatial donor (D)-acceptor (A) interlocked network for achieving NIR-II OPTAs. Two isomers, 4MNVDPP and 6MNVDPP were synthesized and formulated into NPs. 6MNVDPP, which has a larger electrostatic potential difference, exhibits a compact 3D spatial D-A interlocked network in the crystal form, while 4MNVDPP forms 2D D-D type J-aggregates. Thus, 6MNVDPP NPs show red-shifted NIR absorption and larger molar extinction coefficient than 4MNVDPP NPs. Thanks to the typical NIR-II emission, superior photothermal-stability, high photothermal conversion efficiency (89 %) and reactive oxygen species production capacity, 6MNVDPP NPs exhibit outstanding NIR-II tiny capillary vasculature/tumor imaging ability and synergistic photothermal/photodynamic anti-cancer effect in vivo.

Keywords: 3D Spatial D-A Interlocked Network; Molecular Packing; NIR-II Fluorescence Imaging; Phototheranostics; Structural Isomerization.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Humans
Isomerism
Nanoparticles* / chemistry
Neoplasms*
Photoacoustic Techniques* / methods
Phototherapy
Theranostic Nanomedicine / methods