Rational design of pH-responsive near-infrared spirocyclic cyanines: the effects of substituents and the external environment

Akihiro Sakama; Hyemin Seo; Joji Hara; Yutaka Shindo; Yuma Ikeda; Kotaro Oka; Daniel Citterio; Yuki Hiruta

doi:10.1039/D4CC01484G

Rational design of pH-responsive near-infrared spirocyclic cyanines: the effects of substituents and the external environment†

Akihiro Sakama,

‡^a Hyemin Seo,‡^a Joji Hara,^a Yutaka Shindo,^bc Yuma Ikeda,^a Kotaro Oka,^bcde Daniel Citterio

^a and Yuki Hiruta

*^a

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama, Kanagawa, Japan
E-mail: hiruta@applc.keio.ac.jp

^b Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan

^c School of Frontier Engineering, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa, Japan

^d Waseda Research Institute for Science and Engineering, Waseda University, 2-2 Wakamatsu-cho, Shinjuku-ku, Tokyo 162-8480, Japan

^e College of Medicine, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan

Abstract

pH-responsive spirocyclic cyanine dyes were designed and synthesized. The equilibrium constant for cyclization (pK_cycl) could be rationally controlled by changing the nucleophilic moiety and the side chains. Encapsulation in polymeric micelles inhibited the H-aggregation of the dye, and the pK_cycl could be shifted according to the amphiphilic polymer employed.

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DOI: https://doi.org/10.1039/D4CC01484G
Article type: Communication
Submitted: 01 Apr 2024
Accepted: 13 May 2024
First published: 13 May 2024
This article is Open Access

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Chem. Commun., 2024,60, 5984-5987

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Rational design of pH-responsive near-infrared spirocyclic cyanines: the effects of substituents and the external environment

A. Sakama, H. Seo, J. Hara, Y. Shindo, Y. Ikeda, K. Oka, D. Citterio and Y. Hiruta, Chem. Commun., 2024, 60, 5984 DOI: 10.1039/D4CC01484G

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Chemical Communications

Rational design of pH-responsive near-infrared spirocyclic cyanines: the effects of substituents and the external environment†

Abstract

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Rational design of pH-responsive near-infrared spirocyclic cyanines: the effects of substituents and the external environment

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