Design of Photostable, Activatable Near-Infrared Photoacoustic Probes Using Tautomeric Benziphthalocyanine as a Platform

Naoyuki Toriumi, Norihito Asano, Takayuki Ikeno, Atsuya Muranaka, Kenjiro Hanaoka, Yasuteru Urano, Masanobu Uchiyama

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Near-infrared (NIR) imaging techniques have attracted significant attention for biological and medicinal applications due to the ability of NIR to penetrate deeply into tissues. However, there are very few stable, activatable molecular probes that can utilize NIR light in the wavelength range beyond 800 nm. Herein, we report a new activatable NIR system for photoacoustic imaging based on tautomeric benziphthalocyanines (BPcs). We found that the existence of a free hydroxyl group is crucial for NIR absorption of BPcs. Synthesized water-soluble hydroxy BPcs exhibited high photostability and no fluorescence, which are desirable features for photoacoustic imaging. We synthesized BPcs in which the free hydroxyl group was masked by an esterase-labile or an H2O2-labile group. The photoacoustic signals of these hydroxy-masked BPcs were increased upon NIR excitation at 880 nm in the presence of esterase or H2O2, respectively. These are rare examples of activatable probes utilizing NIR light at around 900 nm.

Original languageEnglish
Pages (from-to)7788-7791
Number of pages4
JournalAngewandte Chemie - International Edition
Volume58
Issue number23
DOIs
Publication statusPublished - 2019 Jun 3
Externally publishedYes

Keywords

  • dyes/pigments
  • near-infrared spectroscopy
  • photoacoustic imaging
  • phthalocyanines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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