title: Synthesis and characterization of water-soluble polythiophene derivatives for cell imaging.
abstract: In this work, four water-soluble polythiophene derivatives (PT, PT-DDA, PT-ADA, and PT-ADA-PPR) with different pendant moieties were synthesized via oxidative copolymerization by FeCl3. By increasing the hydrophobic ability of side chain moieties, there is a gradually blue shift for the maximum absorption wavelength and red shift for the maximum emission wavelength, a reducing trend for fluorescence quantum yields, a growing trend for Stokes shift, and an increasing trend for the mean sizes in the order of PT, PT-ADA, and PT-DDA. All the synthesized polymers show low toxicity and good photostability and accumulate in the lysosomes of A549 cells. Furthermore, the introduction of porphyrin group to PT-ADA side chain (PT-ADA-PPR) broadens the absorption and emission ranges of PT-ADA. PT-ADA-PPR could be excited at two different excitation wavelengths (488 nm and 559 nm) and exhibits two emission pathways, and dual-color fluorescence images (orange and red) of PT-ADA-PPR accumulated in A549 cells are observed. Thus, PT-ADA-PPR could be used as an excellent dual-color fluorescent and lysosome-specific imaging material.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Fengyan
authors.initials: F
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Meng
authors.initials: M
authors.lastname: Li
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Bing
authors.initials: B
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Jiangyan
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Yongqiang
authors.initials: Y
authors.lastname: Cheng
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Libing
authors.initials: L
authors.lastname: Liu
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Fengting
authors.initials: F
authors.lastname: Lv
authors.affiliation: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.
authors.forename: Shu
authors.initials: S
authors.lastname: Wang
mesh_terms: D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D008247:Lysosomes / Q000378:metabolism; D008856:Microscopy, Fluorescence; D049329:Nanostructures / Q000737:chemistry / Q000633:toxicity; D010316:Particle Size; D011108:Polymers / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity; D011166:Porphyrins / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity; D014867:Water / Q000737:chemistry
chemical_list: D011108:Polymers; D011166:Porphyrins; D013876:Thiophenes; D014867:Water; C066730:polythiophene