Rational Design and Application of an Indolium-Derived Heptamethine Cyanine with Record-Long Second Near-Infrared Emission

Abstract

Open AccessCCS ChemistryRESEARCH ARTICLE6 Jun 2022Rational Design and Application of an Indolium-Derived Heptamethine Cyanine with Record-Long Second Near-Infrared Emission Xiaoxie Ma†, Yurou Huang†, Syed Ali Abbas Abedi, Heejeong Kim, Tan Teck Boon Davin, Xiaogang Liu, Wen-Chao Yang, Yao Sun, Sheng Hua Liu, Jun Yin, Juyoung Yoon and Guang-Fu Yang Xiaoxie Ma† Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Yurou Huang† Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Syed Ali Abbas Abedi Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372 , Heejeong Kim Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750 , Tan Teck Boon Davin Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372 , Xiaogang Liu Fluorescence Research Group, Singapore University of Technology and Design, Singapore 487372 , Wen-Chao Yang Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Yao Sun Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Sheng Hua Liu Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Jun Yin *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 , Juyoung Yoon *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750 and Guang-Fu Yang *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] Key Laboratory of Pesticide and Chemical Biology (Ministry of Education), Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079 https://doi.org/10.31635/ccschem.021.202101630 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Heptamethine cyanine dyes, typified by indocyanine green, have been extensively employed as bioimaging indicators and theranostic agents. Significant efforts have been made to develop functional heptamethine cyanine dyes with outstanding bioimaging and theranostic utilities. In this work, we rationally designed and successfully developed a novel indolium-like heptamethine cyanine dye by installing indolium-derived polycyclic aromatic hydrocarbons on the terminal ends of a conjugated polyene backbone. This dye showed excellent photostability and showed bright fluorescent emission in the second near-infrared (NIR-II) window with a peak at approximately 1120 nm. Such long wavelength emission prompted a superior bioimaging resolution in vivo. In particular, this NIR-II dye had the remarkable capability of marking the blood vessels of the hindlimbs, abdomens, and brains of mice. More significantly, this dye involved a typical indolium-like heptamethine skeleton and exhibited two strong absorption bands in the 700–1300 nm NIR range, which endowed it with an intrinsic tumor-targeting capability and a high photothermal conversion efficiency (up to 68.2%), s