Polydiacetylene-based ultrastrong bioorthogonal Raman probes for targeted live-cell Raman imaging

Sidan Tian; Haozheng Li; Zhong Li; Huajun Tang; Mingming Yin; Yage Chen; Shun Wang; Yuting Gao; Xiangliang Yang; Fanling Meng; Joseph W Lauher; Ping Wang; Liang Luo

doi:10.1038/s41467-019-13784-0

Polydiacetylene-based ultrastrong bioorthogonal Raman probes for targeted live-cell Raman imaging

Nat Commun. 2020 Jan 3;11(1):81. doi: 10.1038/s41467-019-13784-0.

Authors

Sidan Tian¹, Haozheng Li², Zhong Li³, Huajun Tang², Mingming Yin¹, Yage Chen², Shun Wang⁴, Yuting Gao¹, Xiangliang Yang^{1

5}, Fanling Meng⁶, Joseph W Lauher⁷, Ping Wang^{8

9}, Liang Luo^{10

11}

Affiliations

¹ National Engineering Research Center for Nanomedicine, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan, 430074, China.
² Britton Chance Center for Biomedical Photonics, Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan, Hubei, 430074, China.
³ Department of Chemistry, Stony Brook University, Stony Brook, NY, 11790, USA.
⁴ MOE Key Laboratory of Fundamental Physical Quantities Measurement & Hubei Key Laboratory of Gravitation and Quantum Physics, PGMF and School of Physics, Huazhong University of Science and Technology, Wuhan, 430074, P. R. China.
⁵ Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China.
⁶ National Engineering Research Center for Nanomedicine, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan, 430074, China. fanlingmeng@hust.edu.cn.
⁷ Department of Chemistry, Stony Brook University, Stony Brook, NY, 11790, USA. joseph.lauher@stonybrook.edu.
⁸ National Engineering Research Center for Nanomedicine, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan, 430074, China. p_wang@hust.edu.cn.
⁹ Britton Chance Center for Biomedical Photonics, Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan, Hubei, 430074, China. p_wang@hust.edu.cn.
¹⁰ National Engineering Research Center for Nanomedicine, College of Life Science and Technology, Huazhong University of Science and Technology, Wuhan, 430074, China. liangluo@hust.edu.cn.
¹¹ Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China. liangluo@hust.edu.cn.

Abstract

Live-cell Raman imaging based on bioorthogonal Raman probes with distinct signals in the cellular Raman-silent region (1800-2800 cm^-1) has attracted great interest in recent years. We report here a class of water-soluble and biocompatible polydiacetylenes with intrinsic ultrastrong alkyne Raman signals that locate in this region for organelle-targeting live-cell Raman imaging. Using a host-guest topochemical polymerization strategy, we have synthesized a water-soluble and functionalizable master polydiacetylene, namely poly(deca-4,6-diynedioic acid) (PDDA), which possesses significantly enhanced (up to ~10⁴ fold) alkyne vibration compared to conventional alkyne Raman probes. In addition, PDDA can be used as a general platform for multi-functional ultrastrong Raman probes. We achieve high quality live-cell stimulated Raman scattering imaging on the basis of modified PDDA. The polydiacetylene-based Raman probes represent ultrastrong intrinsic Raman imaging agents in the Raman-silent region (without any Raman enhancer), and the flexible functionalization of this material holds great promise for its potential diverse applications.

Publication types

Evaluation Study
Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Cells / chemistry
Cells / cytology*
HeLa Cells
Humans
Molecular Imaging / instrumentation
Molecular Imaging / methods*
Molecular Probes / chemical synthesis
Molecular Probes / chemistry*
Polyacetylene Polymer / chemical synthesis
Polyacetylene Polymer / chemistry*
Spectrum Analysis, Raman / instrumentation
Spectrum Analysis, Raman / methods*

Substances

Alkynes
Molecular Probes
Polyacetylene Polymer
polydiacetylene