CN111234813B - 卵泡颗粒细胞近红外荧光探针Nirova-1及其制备方法和应用 - Google Patents
卵泡颗粒细胞近红外荧光探针Nirova-1及其制备方法和应用 Download PDFInfo
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Abstract
本发明属于医学影像造影剂技术领域,具体为活体卵巢卵泡近红外荧光探针Nirova‑1及其制备方法和应用。本发明荧光探针为有机小分子吲哚菁绿(ICG)与人促卵泡激素(FSH)耦合形成的荧光染料‑人促卵泡激素复合体;该复合体使得荧光染料能够特异性的靶向卵巢中的卵泡结构,实现对所有卵泡的近红外荧光标记。该荧光探针结合ICG在近红外区荧光发射的特点与FSH对卵巢内卵泡颗粒细胞特异性靶向结合的性质,可作为卵巢中卵泡的近红外区荧光造影剂,从而对女性卵巢中卵泡数量及发育阶段进行精确有效的检测评估。
Description
技术邻域
本发明属于医学影像造影剂技术领域,具体涉及卵泡颗粒细胞近红外荧光探针及其制备方法和应用。
背景技术
目前针对患有不孕症的育龄或超龄女性,常需要进行对其进行卵巢内成熟与未成熟卵泡检测,目前实施手段为传统B型超声成像技术或经阴道超声成像技术。但该技术仅能观察到二级以上的卵泡(通常在600μm以上),受限于声波波长的局限,超声成像的最高分辨率为百微米级,因此对于更小的卵泡(如原始卵泡,直径仅若干微米)则无法进行检测,导致部分仅残留较小卵泡的患者失去可进一步治疗的希望。而荧光成像由于实时、非入侵性、高时空分辨率等优点,在生命科学领域被广泛应用,近年来其应用领域更推广至临床成像检测及诊断。相较于传统的可见区(400-700nm)的荧光,近红外区(700nm-1700nm)的荧光成像有更深的穿透深度,更低的生物自荧光背景干扰,能够实现更高质量的组织荧光成像。
近年来,多种在近红外区发射荧光的有机染料被设计合成,为近红外区生物组织荧光成像提供了宝贵的物质基础。而2006年由美国国家食品与药物监督管理局(FDA)批准的近红外荧光染料吲哚菁绿(ICG)具有较大的摩尔消光系数,较高的荧光量子产率,较好的水溶性,较快的生物代谢速率,在蛋白标记,手术导航中得到了广泛应用。到目前为止,还未报道利用吲哚菁绿与人促卵泡激素合成的探针对卵巢中卵泡颗粒细胞进行近红外区荧光标记。
发明内容
本发明的目的在于提供一种制备工艺简单、特异性高、光稳定性好的近红外区、卵巢内卵泡颗粒细胞靶向的荧光探针及其制备方法和应用。
本发明提供的卵泡颗粒细胞近红外荧光探针,为有机小分子吲哚菁绿(ICG)与人促卵泡激素(FSH)耦合形成的荧光染料-人促卵泡激素偶联复合体,记为荧光探针Nirova-1;其化学结构式为:
本发明所制备的荧光探针其吸收和发射光谱参见图1,与FSH耦合后对ICG及其衍生物的光学特征峰没有影响,明场及近红外CCD照片参加图2.图3。
本发明中,FSH原料选自:重组人促卵泡激素α、重组人促卵泡激素β、重组人促卵泡激素、尿促卵泡激素、垂体提纯人促卵泡激素。
本发明提供的上述卵泡颗粒细胞近红外荧光探针的制备方法,具体步骤如下:
称取FSH充分溶解于磷酸盐缓冲溶液中,同时称取ICG-MAL溶于二甲亚砜后用反应溶液体系进行稀释,在温度4℃-37℃条件下加入FSH溶液,搅拌反应20-30h;然后提纯,去除未反应的ICG-MAL及过量磷酸盐,冻干,即得到卵泡颗粒细胞近红外荧光探针Nirova-1。
本发明中,为保证Nirova-1荧光探针FSH端的生物活性,反应溶液体系包括磷酸盐缓冲液(1X,pH7.2-7.4)、生理盐水、超纯蒸馏水,反应温度应控制在4℃-37℃,搅拌速度100-300转/分钟为宜,搅拌时间为20-30小时,时长可通过质谱监测反应情况而进行调整。
本发明中,为了保证FSH的反应效率,投料时加入过量的ICG-MAL,通常ICG:FSH为100:1-1000:1(按摩尔比),故反应结束后进行提纯,提纯方法为 使用3kDa(Amicon)的超滤管对该荧光探针进行分离提纯,也可以选择孔径适当的透析袋进行透析提纯。
本发明中,为了便于后续储存、运输及使用,将75IU(以FSH量计算,FSH为5.5μg)的荧光探针Nirova-1溶液封装于一次使用型玻璃瓶中,利用冷冻干燥机对该荧光探针溶液进行冻干,从而得到粉体,避光保存,短期储存放置于2-8℃,长期储存应放置于-20℃。开启并溶解后应立即一次皮下注射使用。
本发明中,把ICG-MAL替换为ICG Carboxylate,可获得同样分子,故应涵盖于本发明保护范围内。
本发明中,直接使用ICG与FSH当量混合,同样可以获得效果相近的复合体,故应涵盖于本发明保护范围内。
本发明荧光探针结合了ICG在近红外区荧光发射的特点与FSH对卵巢内卵泡颗粒细胞特异性靶向结合的性质,可作为卵巢中卵泡的近红外区荧光造影剂,从而对女性卵巢中卵泡数量及发育阶段进行精确有效的检测评估。具体做法如下:
取适量荧光探针分散于100-300μL 0.9%注射用氯化钠溶液中,使该造影剂每100μL 内含有1.8-5.5μg FSH。
本发明荧光探针用作卵巢内卵泡颗粒细胞的近红外荧光标记。
本发明提供了一种基于ICG及其衍生物的近红外区荧光探针Nirova-1及其制备方法,该荧光探针作为近红外窗口的荧光成像探针具有较深的穿透深度和较高的空间分辨率,通过FSH与卵泡上颗粒细胞的特异性G-偶联蛋白受体结合,实现卵泡特异性靶向标记,所述探针制备方法简单、稳定性及可重复性好。
附图说明
图1为ICG和FSH耦合形成荧光探针Nirova-1的吸收和发射光谱图。
图2为荧光探针Nirova-1的明场照片。
图3为荧光探针Nirova-1在近红外CCD下采集的照片。
图4为利用荧光探针Nirova-1标记的C57小鼠卵巢在近红外CCD下采集的照片。
具体实施方式
实施例1:
称取ICG-MAL(1.1mg,1.3µmol)溶于DMSO中,人促卵泡激素(FSH)25 µg溶于0.1mL1X磷酸缓冲液(PBS)中。FSH-PBS体系加入1mM二硫苏糖醇(DTT)进行预处理后,在1 mL玻璃反应器中加入上述溶液体系,使其染料与蛋白的摩尔比为100:1,在4℃恒温搅拌20h,转如3kDa(Amicon)的超滤管,4500转/分钟,15分钟离心透析,用1X磷酸盐缓冲溶液重复该步骤两次。
实施例2:
称取ICG-MAL(1.1mg,1.3µmol)溶于DMSO中,人促卵泡激素(FSH)25 µg溶于0.1mL1X磷酸缓冲液(PBS)中。FSH-PBS体系加入1mM 三(2-羧乙基)膦(TCEP)进行预处理后,在1 mL玻璃反应器中加入上述溶液体系,使其染料与蛋白的摩尔比为100:1,在4℃恒温搅拌20h,转如3kDa(Amicon)的超滤管,4500转/分钟,15分钟离心透析,用1X磷酸盐缓冲溶液重复该步骤两次。
实施例3:
称取ICGCarboxylate (1mg,1.3µmol)溶于DMSO中,人促卵泡激素(FSH)25 µg溶于0.1mL1X磷酸缓冲液(PBS)中。在1 mL玻璃反应器中加入上述溶液体系,同时加入2.3µL EDC(1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐)储备水溶液,使体系内染料与蛋白的摩尔比为100:1,染料与EDC的摩尔比为1:1,在4℃恒温搅拌20h,转如3kDa(Amicon)的超滤管,4500转/分钟,15分钟离心透析,用1X磷酸盐缓冲溶液重复该步骤两次。
实施例4:
将麻醉的小鼠尾静脉注射100μL,FSH活性成分为75IU的荧光探针Nirova-1,2小时后取其双侧卵巢,用808nm 外置激光器照射,激光器功率密度为100mW/cm2,1200 nm滤光片可进行观测(参见图4)。
Claims (5)
2.根据权利要求1所述的制备方法,其特征在于,所述FSH原料选自:重组人促卵泡激素α、重组人促卵泡激素β、尿促卵泡激素、垂体提纯人促卵泡激素。
3.根据权利要求1所述的制备方法,其特征在于,所述反应溶液体系包括磷酸盐缓冲液、生理盐水、超纯蒸馏水;搅拌速度100-300转/分钟。
4.根据权利要求1所述的制备方法,其特征在于,为了保证FSH的反应效率,投料时加入过量的ICG,反应结束后进行提纯,提纯方法为使用3kDa的超滤管进行分离提纯,或者采用孔径适当的透析袋进行透析提纯。
5.根据权利要求1所述的制备方法,其特征在于,为了便于后续储存、运输及使用,将75IU的荧光探针Nirova-1溶液封装于一次使用型玻璃瓶中,利用冷冻干燥机对该荧光探针溶液进行冻干而得到粉体,避光保存。
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