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目的合成末端取代基为甘氨酸甲酯的吲哚七甲川菁染料(PLGAS-1),研究其作为光声成像造影剂的效果。方法 3-溴丙酸经氯代后与甘氨酸甲酯盐酸盐成3-溴丙酰胺甲酯(XBXA-3)后,再与2,3,3-三甲基-3H吲哚反应,制得季铵盐JAY-1,进而与2-氯-3-羟次甲基环己烯醛缩合制得目标化合物PLGAS-1。测定目标物的最大吸收波长、发射波长及通过建立体外仿体模型,对比研究PLGAS-1和吲哚菁绿(ICG)及金纳米棒(CTAB-7-760)的光声信号强度。结果合成并确证了PLGAS-1的化学结构,其最大吸收和发射波长均在近红外区;体外光声成像研究显示:相同实验条件下,PLGAS-1的光声成像信号强度明显高于ICG和CTAB-7-760,且其光声信号强度与浓度有良好的线性关系。结论新型吲哚七甲川菁染料可为新型光声成像造影剂的研究提供思路。
Objective To synthesize indole heptamethyocyanine dye (PLGAS-1) whose terminal substituent is glycine methyl ester and study its effect as a photoacoustic contrast agent. Method 3-Bromopropionic acid was reacted with 2, 3, 3-trimethyl-3H-indole after chlorination with methyl glycinate hydrochloride to form 3-bromopropionamide methyl ester (XBXA-3) Quaternary ammonium salt JAY-1, and then with 2-chloro-3-hydroxymethyl cyclohexenal condensation of the target compound PLGAS-1. The maximum absorption wavelength and emission wavelength of the target were determined and the photoacoustic signal intensities of PLGAS-1, indocyanine green (ICG) and gold nanorods (CTAB-7-760) were compared by establishing the in vitro model. Results The chemical structure of PLGAS-1 was synthesized and confirmed. The maximum absorption and emission wavelengths of PLGAS-1 were in the near-infrared region. In vitro photoacoustic imaging showed that under the same experimental conditions, the photoacoustic signal intensity of PLGAS-1 was significantly higher than that of ICG and CTAB-7-760, and its photoacoustic signal intensity and concentration have a good linear relationship. Conclusion The new indole heptamethyocyanine dye can provide a new idea for the research of new photoacoustic imaging contrast agent.