targeted thiazole orange derivative with folate synthesis, fluorescence and in vivo fluorescence imaging针对噻唑橙导数叶酸合成、荧光和体内荧光成像.pdf

Molecules 2010, 15, 6983-6992; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Targeted Thiazole Orange Derivative with Folate: Synthesis, Fluorescence and in Vivo Fluorescence Imaging Xuening Fei 1,2,*, Yingchun Gu1,2, Yiqi Wang 2, Qingyang Meng 2 and Baolian Zhang 2 1 School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, China; E-Mail: guyingchun@ (Y.-C.G.) 2 Department of Material Science and Engineering, Tianjin Institute of Urban Construction, Tianjin, 300384, China; E-Mail: yiqi3778@163.com (Y.-Q.W.); dream12114@163.com (Q.-Y.M.); ybysw@126.com (B.-L.Z.) * Author to whom correspondence should be addressed: E-Mail: xueningfei@126.com. Received: 19 August 2010; in revised form: 15 September 2010 / Accepted: 25 September 2010 / Published: 11 October 2010 Abstract: A Thiazole Orange conjugated with folate derivative was synthesized in two steps. Firstly, folate was coupled with 1-(3-aminopropyl)-4-methylquinolinium bromide to afford folate-methylquinolinium bromide, which then reacted with benzothiazolium to obtain the title folate-conjugated compound. The compound was evaluated by 1H-NMR MS, TG/DTA and fluorescence spectroscopic methods. The title compound could selectively target folate receptor expressing tumors according to the in vivo fluorescence imaging preliminarily performed on nude mice with breast tumors. Keywords: thiazole orange; folate; synthesis; tar