De Novo Construction of pKa‐Tunable Xanthene Molecules for pH Sensitive Fluorescence Navigation

Author:

Zhang Li‐Na1,Chen Shan‐Yong1,Shi Lei1,Ran Xiao‐Yun1,Zhang Hong1,Moon Huiyeon2,Lee Yubin2,Yu Xiao‐Qi3,Kim Jong Seung2,Li Kun1ORCID

Affiliation:

1. Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry Sichuan University Chengdu Sichuan 610064 China

2. Department of Chemistry Korea University Seoul 02841 South Korea

3. Asymmetric Synthesis and Chiral Technology Key Laboratory of Sichuan Province Department of Chemistry Xihua University Chengdu Sichuan 610064 China

Abstract

AbstractpH is spatiotemporal variable dynamically in physiological and pathological processes, and the tiny pH changes can result completely different physiological processes. However, the major drawbacks of conventional pH‐activatable probes are their large acid‐base transition width and the challenge to adjust their pKa suitable for various application. In response to these issues, a novel approach is proposed to realize sensitive response and a general strategy to construct a multicolor and pKa‐tunable xanthene‐based platform. In these probes, the narrowest acid‐base transition range is just 1 pH units, achieved by introducing the electron‐rich pyridine as ingenious proton catcher. Especially, Si‐4Py owns near‐infrared (NIR) signal and pKa of 5.56, which is successfully used for the rapid and high‐contrast imaging of distal metastatic tumors. This has significant implications for guiding surgeons in the removal of these tumors and ultimately improve patient outcomes. Additional, the sustainably innovative strategy proposed by this work can serve as effective reference in pH probe development.

Funder

National Natural Science Foundation of China

National Research Foundation of Korea

Science and Technology Plan Projects of Tibet Autonomous Region

Publisher

Wiley

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