title: Nonplanar Monocyanines: Meso-Substituted Thiazole Orange with High Photostability and Their Synthetic Strategy as well as a Cell Association Study.
abstract: A convenient approach for the direct synthesis of meso-substituted thiazole orange (meso-TO) analogues has been unprecedentedly developed through the AlCl3-catalyzed reaction of parent TO with benzyl alcohol derivatives. Single-crystal X-ray structures show that the prepared new meso-TO analogues are nonplanar, forming a sharp contrast to planar TO. The spectral properties show that nonplanar meso-TO analogues do not aggregate, existing in monomer form (M) in PBS buffer, and have little effect of solvatochromism in different solvents. In comparison with the parents, meso-TO analogues exhibit a large Stokes shift, excellent light fastness, and inertness to singlet oxygen. A cellular association study demonstrates that incorporation of a benzyl group at the meso position methine of parent TO can decrease the cytotoxicity, change staining area in cells, and emit long-wavelength fluorescence for an extended time, which are useful for the development of smarter TOs for imaging in biological science.
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Li
authors.initials: L
authors.lastname: Guan
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Anyang
authors.initials: A
authors.lastname: Li
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Yinyin
authors.initials: Y
authors.lastname: Song
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Mengqi
authors.initials: M
authors.lastname: Yan
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Dengfeng
authors.initials: D
authors.lastname: Gao
authors.affiliation: School of Life Sciences and Technology, Xidian University , Xi'an 710071, People's Republic of China.
authors.forename: Xianghan
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, Northwest University , Xi'an 710069, People's Republic of China.
authors.forename: Bin
authors.initials: B
authors.lastname: Li
authors.affiliation: Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, Ministry of Education, College of Chemistry and Materials Science, Northwest University , Xi'an 710127, People's Republic of China.
authors.forename: Lanying
authors.initials: L
authors.lastname: Wang
mesh_terms: D000818:Animals; D052160:Benzothiazoles / Q000737:chemistry*; D002232:Carbocyanines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D005453:Fluorescence; D006801:Humans; D008027:Light; D061986:MCF-7 Cells; D009682:Magnetic Resonance Spectroscopy; D018613:Microscopy, Confocal; D008958:Models, Molecular; D015394:Molecular Structure; D055668:Photochemical Processes; D000072417:Protein Domains; D011804:Quinolines / Q000737:chemistry*; D051381:Rats; D026082:Singlet Oxygen / Q000737:chemistry; D012997:Solvents
chemical_list: D052160:Benzothiazoles; D002232:Carbocyanines; D011804:Quinolines; D012997:Solvents; C051000:thiazole orange; D026082:Singlet Oxygen