CN105017297B - 一种氟硼吡咯类衍生荧光化合物及其应用 - Google Patents

一种氟硼吡咯类衍生荧光化合物及其应用 Download PDF

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CN105017297B
CN105017297B CN201410173946.8A CN201410173946A CN105017297B CN 105017297 B CN105017297 B CN 105017297B CN 201410173946 A CN201410173946 A CN 201410173946A CN 105017297 B CN105017297 B CN 105017297B
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陈令新
高敏
景晓彤
陈浩
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Abstract

本发明涉及用于检测硫化氢(H2S)的荧光探针,具体的说是一种氟硼吡咯类衍生荧光化合物及其应用。氟硼吡咯类衍生荧光化合物如通式Ⅰ所示,并以所述氟硼吡咯类化合物作为H2S的荧光探针。本发明H2S荧光探针的这类化合物,在H2S存在下对应的荧光强度发生变化,可用于H2S的检测,并可大大降低外部检测条件的干扰,提高检测精度。这类化合物作为荧光探针可用于细胞内外H2S的检测,不仅对阐明H2S对血管新生产生具有重要的科学意义,而且为H2S在不同浓度下对肿瘤凋亡和转移奠定理论基础。

Description

一种氟硼吡咯类衍生荧光化合物及其应用
技术领域
本发明涉及用于检测硫化氢(H2S)的荧光探针,具体的说是一种氟硼吡咯类衍生荧光化合物及其应用。
背景技术
目前认为硫化氢(H2S)是继NO和CO之后被发现的第三种气体信号分子,内源性H2S在体内由不同的组织和细胞产生,在生理浓度水平下,H2S参与一系列的生理调控过程,与此同时,三个气体递质硫化氢、一氧化氮和一氧化碳之间还通过各种交互作用调控着人体的健康与疾病,但目前对H2S的了解远少于NO和CO。内源性H2S作为小分子物质,在脂溶性溶剂中的溶解度为水中的5倍,可自由通过细胞膜。H2S在线粒体内谷胱甘肽作用下被氧化为硫酸盐和硫代硫酸盐,在细胞质中少量H2S通过甲基化作用转变为低毒的甲硫醇和二甲基硫酸盐,通过肾脏、肠道和肺脏排出。
哺乳动物体内的H2S主要通过含硫的半胱氨酸代谢生成。胱硫醚-γ-裂解酶(eystathionine-γ-lyase,CSE)和胱硫醚-β-合成酶(cystathionine-β-synthase,CBS)是体内转硫途径的关键酶,对H2S的产生以及含硫化合物的代谢具有重要调节作用,CSE主要在主动脉、肺动脉、尾动脉、肠系膜动脉和门静脉上有表达;相反CBS主要分布在神经系统内;在回肠、肾脏和肝脏中则同时有CBS和CSE的表达;一些种类的癌细胞也可产生H2S。
传统的气体检测方法有电化学法、化学发光法、电子自旋共振波谱法和紫外可见光谱法等,但上述方法往往需要试样预处理,需要破坏组织或裂解细胞,并且耗时长,相对成本较高。故而,上述检测方法不能直接检测细胞内硫化氢的真实状态和浓度,难以真正反映细胞内硫化氢原位实时活动规律及调控机制。因此,实验技术已经大大地影响到对硫化氢的检测以及其效应信号通道的研究。虽然上述每一种方法在一定条件下都是可行的,但是关于生命体中H2S的研究所遇到的瓶颈是缺少灵敏而又专一地检测生命系统中H2S靶向浓度变化的检测工具,由此可见,开发一种新的能够实现对生命体内H2S水平进行靶向检测的生物医学工具将是该研究领域的突破点。
发明内容
本发明的目的在于提供一种氟硼吡咯类衍生荧光化合物及其应用。
为实现上述目的,本发明采用的技术方案为:
一种氟硼吡咯类衍生荧光化合物,如通式Ⅰ所示,
通式Ⅰ中:
R1为连硫邻苯二甲酸、连硒邻苯二甲酸或连碲邻苯二甲酸基团;
R2为连硫邻苯二甲酸、连硒邻苯二甲酸、连碲邻苯二甲酸基团、丁基三苯基基团、N-丙基吗啉基团或C1-25的烷基链;
X为H或卤素;
Y为N或C;
Z为N或O;
进一步的说,所述通式Ⅰ中R1为连硫邻苯二甲酸;R2为丁基三苯基基团或N-丙基吗啉基团;X为H;Y为N;Z为O。
一种氟硼吡咯类化合物的应用,以所述通式Ⅰ所示的氟硼吡咯类化合物作为硫化氢的荧光探针。
一种荧光探针,荧光探针为通式Ⅰ所示的以(BODIPY)染料作为荧光母体,并在母体上R2取代基位置引入对具备线粒体、溶酶体、内质网定位功能团的季磷盐、吗啉、C1-25烷基碳链、连硫邻苯二甲酸、连硒邻苯二甲酸或连碲邻苯二甲酸基团。
所述荧光探针用于定性/定量的检测生理环境下、细胞或生物体内的硫化氢。
本发明的有益效果:
本发明化合物用于作为H2S荧光检测的探针,其在H2S存在下对应的荧光强度发生变化,进而可用于水体系、模拟生理环境和细胞内HNO水平的检测。本发明用于H2S荧光探针的这类化合物,在H2S存在下对应的荧光强度发生变化,可用于H2S的检测,并可缩减样品处理时间、大大降低检测成本和提高检测精度。这类化合物作为荧光探针可用于细胞内外H2S浓度的检测,不仅对阐明H2S对血管新生产生具有重要的科学意义,而且为H2S在不同浓度下对肿瘤凋亡和转移奠定理论基础。
附图说明
图1为本发明实施例提供的采用的荧光探针对H2S检测前后荧光变化。
图2为本发明实施例提供的所采用的荧光探针对H2S的选择性示意图;其中,横坐标从左至右依次为:硫化氢、谷胱甘肽、半胱氨酸、硫代硫酸钠、亚硫酸氢钠、维生素C、硫辛酸、环氧硫蛋白、金属硫蛋白、维生素E、尿酸、组氨酸和酪氨酸。
具体实施方式
氟硼吡咯类衍生荧光化合物通式为:
式Ⅰ中:
R1为连硫邻苯二甲酸、连硒邻苯二甲酸或连碲邻苯二甲酸基团;
R2为连硫邻苯二甲酸、连硒邻苯二甲酸、连碲邻苯二甲酸基团、丁基三苯基基团、N-丙基吗啉基团或C1-25的烷基链;
X为H或卤素;
Y为N或C;
Z为N或O;
优选:通式Ⅰ中X为H;Y为N;Z为O时,所述氟硼吡咯类化合物的通式为:
通式II中:
R1为连硫邻苯二甲酸、连硒邻苯二甲酸或连碲邻苯二甲酸基团;
R2为连硫邻苯二甲酸、连硒邻苯二甲酸、连碲邻苯二甲酸基团、丁基三苯基基团或N-丙基吗啉基团;
将通式Ⅰ与待测定水体、模拟生理环境或细胞内的H2S反应从而导致荧光强度的改变,所得通式III结构的化合物;
将通式II结构应用于检测H2S时,其与H2S作用后,生成具有通式IV结构的化合物,从而导致荧光强度的改变;
通式II可对H2S进行定性、定量的检测。
本发明中使用的术语“烷基”包括直链烷基和支链烷基。如提及单个烷基如“丙基”,则只特指直链烷基,如提及单个支链烷基如“异丙基”,则只特指支链烷基。例如,“C1-6烷基”包括C1-4烷基、C1-3烷基、甲基、乙基、正丙基、异丙基和叔丁基。类似的规则也适用于本说明书中使用的其它基团。
本发明中使用的术语“卤素”包括氟、氯、溴和碘。
本发明中使用的术语“苄基”是指-CH2-Ph基团。当用“任选取代”修饰苄基时,指该苄基可以未取代的形式存在,或者可被合适的取代基在任何合适的位置取代。合适的取代基包括但不限于H、C1-18烷基、CN、COOH、NH2、NO2、OH、SH、C1-6烷氧基、C1-6烷基氨基、C1-6酰氨基、卤素、或C1-6卤代烷基等,只要最终形成的化合物具有本发明期望的性质。优选苄基由COOH、NH2、OH、C1-6烷氧基、卤素任选取代。
具体实施方式
实施例用于进一步说明本发明,但本发明不限于实施例。
实施例1.氟硼吡咯类衍生荧光化合物的制备:
通式Ⅰ中所示氟硼吡咯类化合物由市售对羟基苯乙酮和苯甲醛反应起,合成响应的荧光团BODIPY,然后在荧光团相应的位置分别修饰上不同的定位基团。最后将修饰定位基团的荧光团与连硫邻苯二甲酸在二氯甲烷溶剂中,由DMAP和EDC催化反应生成相应的氟硼吡咯类衍生荧光化合物。具体实施例如下:
制备式一化合物:
在氩气保护下,BODIPY荧光团(52.9mg,0.1mmol)及连硫邻苯二甲酸(67.4mg,0.22mmol)、DMAP(24.4mg,0.2mmol)、EDCI(19.2mg,0.1mmol)溶于盛有20ml干燥的二氯甲烷的50ml烧瓶中,常温条件下搅拌24h,TLC追踪反应进度。粗产品由氢溴酸中和后由NaBr的饱和溶液洗涤至中性,二氯甲烷萃取,硫酸钠干燥有机层后旋蒸。采用柱层析(200-300目)分离法对产品进行分离,洗脱剂为甲醇。收集绿色组分,蒸干溶剂后得到式一所示化合物33mg,收率:30%。
化合物式一的1H NMR(500MHz,CDCl3-D1)δ(ppm):6.76(s,2H),7.20-7.90(m,32H),8.35(d,2H),12.75(s,2H).LC-MS(API-ES):m/zC60H38BF2N3O8S4Calcd1105.1603,found[M-H]-1104.1529.
制备式二化合物:
在氩气保护下,取连有三苯基膦基团的荧光团(84.6mg,0.1mmol)及连硫邻苯二甲酸(33.7mg,0.11mmol)、DMAP(12.2mg,0.1mmol)、EDCI(9.6mg,0.05mmol)于盛有20ml干燥的二氯甲烷的50ml烧瓶中,常温下搅拌24h,TLC追踪反应进度。粗产品由氢溴酸中和后,用NaBr的饱和溶液洗涤至中性,二氯甲烷萃取,硫酸钠干燥有机层后旋蒸。所得固体用二氯甲烷溶解后,用硅胶柱色谱(200-300目)分离。洗脱剂为乙酸乙酯和甲醇梯度洗脱(2:1-0:1/v/v),收集绿色组分,蒸干溶剂后得到式二所示化合物27.2mg,收率:24%。
式二化合物的1H NMR(500MHz,CDCl3-D1)δ(ppm):1.32-1.57(m,6H),4.07(t,2H),6.60(s,2H),6.99-7.85(m,39H),8.41(s,2H),12.73(s,1H).LC-MS(API-ES):m/zC68H52BF2N3O5PS2 +Calcd1134.3142,found[M+]1134.3141.
制备式三化合物:
取已制备的连有线粒体定位基团的荧光团(84.6mg,0.1mmol)及连硫邻苯二甲酸(33.7mg,0.11mmol)、4-二甲氨基吡啶DMAP(12.2mg,0.1mmol)、1-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐EDCI(9.6mg,0.05mmol)溶于盛有20ml干燥的二氯甲烷的50ml烧瓶中,常温条件下搅拌24h,TLC追踪反应进度。粗产品由氢溴酸中和后由NaBr的饱和溶液洗涤至中性,二氯甲烷萃取,硫酸钠干燥有机层后旋蒸。采用柱层析分离法对产品进行分离,洗脱剂为乙酸乙酯和甲醇梯度洗脱(2:1-0:1/v/v)。收集绿色组分,蒸干溶剂后得到式三所示化合物24.5mg,收率:26%。
式三化合物的1H NMR(500MHz,CDCl3-D1)δ(ppm):1.82(m,2H),2.34-2.45(m,6H),3.64(t,4H),4.05(t,2H),6.70(s,2H),6.99-7.93(m,24H),8.50(s,2H),12.73(s,1H).LC-MS(API-ES):m/z C53H43BF2N4O6S2Calcd944.2685,found[M+H]+945.2759.
另外,通式Ⅰ所示的其它化合物按照上述的记载制备获得。
现以式二所指化合物为例说明测定过程,以下实施例中涉及到的探针化合物均为式二所指化合物:
实施例2
将制备所得式二化合物作为探针应用于水体系、模拟生理环境和细胞内进行对HNO的检测,模拟生理条件,以下各项实验均在pH=7.4条件下进行(HEPES缓冲溶液,浓度为40mM),探针浓度采用2μM。
上述制备所得式二化合物对H2S的光谱响应;于10ml比色管中加入2μM式二化合物,再加入40mM HEPES,然后加入10μM H2S,超纯水定容到10ml,摇匀溶液平衡10min后,将上述工作液加入荧光皿中测定荧光光谱。荧光光谱变化如图1所示。由图1所示该化合物可用于实现生物体内的H2S检测。同时,本发明实施例提供的探针与硫化氢反应后产物结构如下;
实施例3
式二化合物对硫化氢的选择性
测试液pH采用HEPES缓冲溶液控制。取多个10ml比色管,并在每个10ml比色管中加入2μM式二化合物,再加入HEPES缓冲液,然后分别加入如图2所示,待测物依次为:硫化氢、谷胱甘肽、半胱氨酸、硫代硫酸钠、亚硫酸氢钠、维生素C、硫辛酸、环氧硫蛋白、金属硫蛋白、维生素E、尿酸、组氨酸和酪氨酸。最后用超纯水定容到10ml。摇匀溶液,25℃下平衡10min后,将各个比色管中工作液分别倒入到荧光皿中测定荧光光谱。式二化合物对H2S的选择性如图2所示。并由图可知式二化合物对硫化氢具有很好的选择性,与H2S作用后,式二化合物对应的荧光增强。
以上内容是结合具体的优选实施方式对本发明所作的进一步详细说明,不能认定本发明的具体实施只局限于这些说明。对于本发明所属技术领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干简单推演或替换,都应当视为属于本发明的保护范围。作为荧光染料是本发明新化合物的一种用途,不能认定本发明的化合物仅用于荧光染料,对于本发明所属技术领域的普通技术人员来说,在基于本发明化合物用作荧光染料的相同作用机理的考虑下,还可以做出若干简单推理,得出本发明的化合物的其他应用用途,都应当视为属于本发明的保护范围。

Claims (3)

1.一种氟硼吡咯类衍生荧光化合物,其特征在于如通式Ⅰ所示,
通式Ⅰ中:
R1
R2三苯基鏻丁基基团、N-吗啉丙基基团或C1-25的烷基链;
X为H或卤素;
Y为N;
Z为O。
2.按权利要求1所述的氟硼吡咯类衍生荧光化合物,其特征在于:所述通式Ⅰ中R1R2为三苯基鏻丁基基团或N-吗啉丙基基团;X为H;Y为N;Z为O。
3.一种权利要求1所述的氟硼吡咯类衍生荧光化合物非诊断目的的应用,其特征在于:以所述通式Ⅰ所示的氟硼吡咯类化合物作为硫化氢的荧光探针。
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