Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability

Liu, Chunchen1; Ma, Huilong1; Hu, Zhubin2; Tian, Rui3,4; Ma, Rui1; Xu, Yifan1; Wang, Xinyuan1; Zhu, Xingfu1; Yu, Panpan1; Zhu, Shoujun5; Sun, Haitao2; Liang, Yongye1

2021-09-02

10.3389/fchem.2021.739802

Frontiers in Chemistry   影响因子和分区

2296-2646

Molecular fluorophores emitting in the second near-infrared (NIR-II) window with good renal excretion ability are favorable for in vivo bio-imaging and clinical applications. So far, renally excretable fluorophores are still less studied. Understanding the influences of molecular structure on optical properties and renal excretion abilities are vital for fluorophore optimization. Herein, a series of shielding unit-donor-acceptor-donor-shielding unit (S-D-A-D-S) NIR-II molecular fluorophores are designed and synthesized with dialkoxy chains substituted benzene as the S unit. The anchoring positions of dialkoxy chains on benzene are tuned as meso-2,6, para-2,5, or ortho-3,4 to afford three fluorophores: BGM6P, BGP6P and BGO6P, respectively. Experimental and calculation results reveal that alkoxy side chains anchored closer to the conjugated backbone can provide better protection from water molecules and PEG chains, affording higher fluorescence quantum yield (QY) in aqueous solutions. Further, these side chains can enable good encapsulation of backbone, resulting in decreased binding with albumin and improved renal excretion. Thus, fluorophore BGM6P with meso-2,6-dialkoxy chains exhibits the highest quantum yield and fastest renal excretion. This work emphasizes the important roles of side chain patterns on optimizing NIR-II fluorophores with high brightness and renal excretion ability.

NIR-II fluorophores shielding unit S-D-A-D-S structure fluorescence performance renal excretion

SCI

英语

第一 ; 通讯

National Natural Science Foundation of China[21772084] ; Fundamental Research Layout of Shenzhen[JCY20180504165657443] ; Guangdong Provincial Natural Science Foundation-Yueshen Joint Found (Youth Project)[2019A1515110464] ; Shenzhen San-Ming Project[SZSM201809085] ; Shenzhen Science and Technology Commission-free exploration/general project[JCYJ20190812151209348] ; Chinese Scholarship Council[201808440345]

Chemistry

Chemistry, Multidisciplinary

WOS:000696675200001

FRONTIERS MEDIA SA

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Key Lab Printed Organ Elect, Dept Mat Sci & Engn, Shenzhen, Peoples R China
2.East China Normal Univ, State Key Lab Precis Spect, Shanghai, Peoples R China
3.Xiamen Univ, State Key Lab Mol Vaccinol & Mol Diagnost, Xiamen, Peoples R China
4.Xiamen Univ, Ctr Mol Imaging & Translat Med, Sch Publ Hlth, Xiamen, Peoples R China
5.Jilin Univ, Coll Chem, State Key Lab Supramol Struct & Mat, Changchun, Peoples R China

Liu, Chunchen,Ma, Huilong,Hu, Zhubin,et al. Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability[J]. Frontiers in Chemistry,2021,9.

Liu, Chunchen.,Ma, Huilong.,Hu, Zhubin.,Tian, Rui.,Ma, Rui.,...&Liang, Yongye.(2021).Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability.Frontiers in Chemistry,9.

Liu, Chunchen,et al."Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability".Frontiers in Chemistry 9(2021).