CN110386931B - 一种人血清蛋白荧光探针及其制法和用途 - Google Patents
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Abstract
一种人血清蛋白荧光探针及其制法和用途,其特征是它有如下结构:
Description
技术领域
本发明属于荧光探针技术领域,具体涉及一种人血清蛋白荧光探针及其制备方法和用途。
背景技术
人血清蛋白(Human Serum Albumin,HSA)是循环系统中最丰富的转运蛋白,在调节渗透压和运输营养、代谢产物及药物的过程中起关键作用。大量研究表明人血清蛋白的异常表达与多种疾病相关,如:冠心病,多发性骨髓瘤,糖尿病,肾脏疾病,神经系统代谢紊乱,慢性间质性肝炎等,因此它被作为临床前诊断的重要潜在参数。血浆中的人血清白蛋白浓度通常为35~50mg/mL,在血清等生物流体中定量检测HSA已成为预防和治疗的重要手段。
目前检测HSA的方法主要包括蛋白质组学,放射免疫测定,电化学。由于无需昂贵的设备和复杂的制备,荧光探针显示出灵敏度高、选择性好等优点。通常用于检测HSA的荧光探针依赖于几种机制,包括GFP(绿色荧光蛋白)模仿策略,基于纳米粒子的荧光增强,染料结合性成像和小分子位点结合。其中,小分子和HSA的某些特定位点的结合更能实现对HSA相比于分子量更小的牛血清蛋白(Bovine Serum Albumin,BSA)的高选择性。然而,它们仍然面临一些缺陷:如检测系统通常受到介质的极性或粘度的干扰等。
我们提供了一种基于扭转分子内电荷转移(Twisted Intra-molecular ChargeTransfer,TICT)机理的快速和高选择性检测HSA的探针NJUP1。该探针具有较低的细胞毒性,良好的灵敏度和选择性,减少甚至避免了介质极性和粘度的干扰,分子量仅为约300,且仅有一个共轭连接双键,具有良好的生物相容性和检测稳定性。
发明内容
本发明的目的在于减小介质极性和粘度的干扰,提供一种新型的高选择性的快速灵敏检测HSA的小分子荧光探针。
本发明的技术方案是提供一种可与人血清蛋白特异性结合的荧光探针,所述探针为,(反式)-(5-(6-(二甲氨基)喹啉-2-基)亚甲基)-2,4噻唑烷二酮,其结构式为:
本发明的目的还在于提供所述的人血清蛋白荧光探针的制备方法,包括以下步骤:
步骤一:将4-N,N-二甲基苯胺用溶剂溶解后,加入巴豆醛和甲苯,搅拌并加热回流,冷却后柱层析分离得到中间体化合物B;
步骤二:取二氧化硒,用溶剂溶解后,加入所述中间化合物B,搅拌并加热回流,冷却后柱层析分离获得中间体化合物C;
步骤三:取所述中间体化合物C,用溶剂溶解后,加入2-硫代-2,4-噻唑烷二酮及尿素,搅拌并加热回流,冷却后过滤,用乙醇洗得到所述人血清蛋白荧光探针。
本发明的目的还在于提供所述人血清蛋白荧光探针的用途,将所述人血清蛋白荧光探针应用于定量检测人血清蛋白的含量。
与现有技术相比,本发明具有如下有益效果:
(1)以喹啉醛为荧光团设计的荧光探针对人血清蛋白的专一性强。
(2)本发明荧光探针自身荧光信号很弱,与人血清蛋白作用后荧光显著增强,并且,具有很高的检测灵敏度。
(3)分子量小,半衰期长。
(4)本发明荧光探针自身的化学性质稳定,无自氧化作用,且与目标物作用迅速。
(5)本发明所提供的制备方法合成路线简单,易于制备,便于推广应用。
本发明人血清蛋白荧光探针性能优异,可为进一步研究细胞中人血清蛋白生物学功能提供了可靠使用的工具。
具体实施方式
下面结合具体实施例对本发明做进一步的解释说明,但具体实施例并不对本发明做任何限定。除非特别说明,实施例中所涉及的试剂、方法均为本领域常用的试剂和方法。
本发明实施例提供人血清蛋白荧光探针,所述荧光探针为,(反式)-(5-(6-(二甲氨基)喹啉-2-基)亚甲基)-2,4噻唑烷二酮,其分子结构式如下式所示:
本发明实施例人血清蛋白荧光探针的制备方法,其特征在于,包括以下步骤:
步骤一:将4-N,N-二甲基苯胺用溶剂溶解后,加入巴豆醛和甲苯,搅拌并加热回流,冷却后柱层析分离得到中间体化合物B;
步骤二:取二氧化硒,用溶剂溶解后,加入所述中间化合物B,搅拌并加热回流,冷却后柱层析分离获得中间体化合物C;
步骤三:取所述中间体化合物C,用溶剂溶解后,加入2-硫代-2,4-噻唑烷二酮及尿素,搅拌并加热回流,冷却后过滤,用无水乙醇淋洗,然后用无水乙醇重结晶得到所述人血清蛋白荧光探针。
其制备线路如下所示:
以下通过实施例对本发明做进一步说明。
实施例1人血清蛋白荧光探针的制备
将2.5g的4-N,N-二甲基苯胺A 18.4mmol溶解在33mL 6M HCl溶液中,加入3.0mL巴豆醛6.8mmol在室温下搅拌1h,然后加入甲苯35mL,反应加热115℃回流过夜,冷却到室温后,除去甲苯层,加入饱和氢氧化钠溶液中和水层,用二氯甲烷萃取溶液,饱和NaCl溶液洗涤两次,无水硫酸钠干燥,过滤,减压浓缩,粗品经硅胶柱层析PE∶EA=4∶1v/v纯化,得到沙褐色固体B(1.5g,58%)。1H NMR(400MHz,CDCl3)δ7.92(d,J=9.3Hz,1H),7.89(d,J=8.5Hz,1H),7.37(d,J=2.8Hz,1H),7.19(d,J=8.4Hz,1H),6.81(d,J=2.8Hz,1H),3.07(s,6H),2.70(s,3H).13C NMR(100MHz,CDCl3)δ(ppm)154.46,148.22,141.60,134.68,128.91,127.82,122.16,119.45,105.39,40.83,24.78.
将1.3g二氧化硒11.52mmol溶解在在二恶烷40mL/水4mL混合溶剂中,在80℃下加热30min,加入1.7g化合物B 9.6mmol,80℃下搅拌4h,TLC检测,将混合物冷却至室温后,通过硅藻土过滤,然后通过少量二氯甲烷将滤渣多次冲洗,滤液在减压下浓缩,得到的粗品经硅胶柱层析PE∶EA=6∶1v/v纯化,得到相应的黄色固体醛C(0.72g,38%)。1H NMR(400MHz,CDCl3)δ10.14(s,1H),8.07(d,J=9.4Hz,1H),8.02(d,J=8.5Hz,1H),7.92(d,J=8.5Hz,1H),7.43(dd,J=9.4,2.7Hz,1H),6.80(d,J=2.6Hz,1H),3.17(s,6H).13C NMR(100MHz,CDCl3)δ(ppm)193.48,150.20,148.87,141.70,134.25,132.24,131.29,119.73,118.13,103.86,40.41.
将100mg醛C 0.5mmol溶解在6mL无水乙醇中,加入67mg2-硫代-2,4-噻唑烷二酮0.5mmol,45mg尿素0.75mmol,加热回流4h,TLC检测反应进行程度,冷却反应混合物,过滤,用冷无水乙醇清洗,无水乙醇重结晶,然后烘干得到棕色固体(0.12g,77%)。1H NMR(600MHz,DMSO-d6)δ13.61(s,1H),8.12(d,J=8.5Hz,1H),7.93(d,J=9.4Hz,1H),7.76(d,J=8.5Hz,1H),7.71(s,1H),7.53(dd,J=9.4,2.8Hz,1H),6.92(d,J=2.6Hz,1H),3.10(s,6H).13C NMR(150MHz,DMSO-d6)δ(ppm)202.89,169.87,149.73,146.86,141.74,134.62,129.85,129.53,128.42,125.53,120.87,104.31,40.49.
实施例2荧光探针与人血清蛋白反应的紫外可见吸收光谱(说明书附图,图2)
利用紫外-可见光分光光度计来测定NJUP1的紫外吸收活性研究。
(1)PBS缓冲液的配制:135mM NaCl,4.7mM KCl,10mM Na2HPO4,2mM NaH2PHO4,pH7.4;
(2)NJUP1探针的配制:将NJUP1用少量的二甲基亚砜溶解配成储备液,按实验最高浓度的10倍配制储备液;
(3)HSA溶液的配制:将HSA用少量的去离子水溶解配制成储备液;
(4)NJUP1吸收光谱的测定条件:NJUP1(10μM),PBS缓冲液(pH 7.4,10mM,含有5%的二甲基亚砜)37℃,使用岛津UV-2550,300nm-800nm波段测得紫外吸收光谱,如图2所示。
实施例3荧光探针与不同浓度的人血清蛋白反应的荧光发射光谱测定(说明书附图,图3)
NJUP1(10μM),PBS缓冲液(pH 7.4,10mM,含有5%的DMSO)37℃加入不同终浓度的人血清蛋白(0.01-50mg/mL),在激发波长为460nm下,电压500V,狭缝5nm*5nm条件下使用日立F-7000荧光分光光度计测得其荧光发射光谱,如图3所示。NJUP1在水中荧光淬灭,4-二甲氨基-2-喹啉荧光团处于“off”状态。当加入HSA后,NJUP1在水/二甲基亚砜混合溶液中荧光变亮,4-二甲氨基-2-喹啉荧光团处于“on”状态,随HSA浓度增加,NJUP1荧光强度在574nm处逐渐增强,因此NJUP1可作为定量检测HSA的荧光探针。本发明的NJUP1具有良好的溶解性和灵敏的荧光探针性质,在荧光开关和传感器、荧光探针、生物标记及荧光成像、有机发光器件等领域具有重要的应用价值。
实施例4荧光探针与阴离子,金属离子,各种氨基酸反应后荧光强度变化(说明书附图,图4)
(1)金属离子溶液的配制:将ZnSO4·7H2O,MnCl2·4H2O,Ca(NO3)2.4H2O,CuSO4·5H2O,MgSO4·7H2O,FeSO4·7H2O,FeCl3,BaCl2,AlCl3,KCl,NaCl,AgNO3,CdCl2,CrCl3,Pb(OAc)2,NiSO4·6H2O,CoSO4·7H2O,HgCl用少量的去离子水溶解配制成储备液;
(2)阴离子溶液的配制:将Na2SO3,Na2S,NaF,NaCl,KBr,KI,Na2CO3,NaHCO3,NaOAc,NaSCN,NaNO2,NaNO3,H2O2,NaOH,Na3PO4,Na2S2O3,Na2SO4用少量的去离子水溶液制备成储备液;
(3)氨基酸溶液的制备:将Ala,Val,Leu,Ile,Pro,Phe,Trp,Met,Gly,Ser,Thr,Cys,Tyr,Asn,Gln,Lys,Arg,His,Asp,Glu用少量的去离子水溶液制备成储备液;
NJUP1(10μM),PBS缓冲液(pH 7.4,10mM,含有5%的二甲基亚砜)37℃加入终浓度为2mM的不同氨基酸(Ala,Val,Leu,Ile,Pro,Phe,Trp,Met,Gly,Ser,Thr,Cys,Tyr,Asn,Gln,Lys,Arg,His,Asp,Glu)、金属离子(Al3+,Ba2+,Ca2+,Cd2+,Co2+,Cr3+,Cu2+,Fe2+,Fe3+,Hg2+,K+,Li+,Mg2+,Mn2+,Na+,Ni2+,Zn2+,Pb2+,Ag+)、阴离子(SO3 2-,S2-,F-,Cl-,Br-,I-,CO3 2-,HCO3 -,OAc-,SCN-,NO2 -,NO-,OH-,PO4 3-,S2O3 2-,SO4 2-)、过氧化氢以及终浓度为10μM的人血清蛋白。在激发波长为460nm下,电压500V,狭缝5nm*5nm条件下用日立F-7000荧光分光光度计进行荧光活性的测定,如图4所示,荧光探针对人血清蛋白的选择性较强,能在各种复杂的环境中对实现对HSA的检测。
实施例5人血清蛋白荧光探针与人血清蛋白及其它结构性质类似的化合物反应的荧光强度的动力学曲线(说明书附图,图5)
NJUP1(10μM),PBS缓冲液(pH 7.4,10mM,含有5%的二甲基亚砜)37℃加入终浓度2.5mM的阿拉伯胶(Acacia),牛血清蛋白(BSA),明胶(Geltin),黄原胶(Xanthan),几丁聚糖(Chitosan),糖化酶(Glucoamylase),胰蛋白酶(Trypsin),酯酶(Lipase),风味蛋白酶(Flavourzyme),溶菌酶(Lysozyme),胃蛋白酶(Pepsin),以及终浓度为0.5mg/mL的人血清蛋白(HSA)。在激发波长为460nm下,电压500V,狭缝5nm*5nm条件下用日立F-7000荧光分光光度计测其在574nm处荧光强度随时间变化的动力学曲线图。糖类和蛋白具有和HSA相似的性质,NJUP1能够专一性的识别HSA,HSA荧光探针的难点之一是区分HSA与BSA,而NJUP1可以在HSA和BSA之间有明显的选择性,HSA的荧光强度是BSA的6倍,如图5所示,荧光探针与人血清蛋白反应后的荧光强度明显高于其他反应物。
实施例6人血清蛋白荧光探针与HSA随时间变化荧光强度变化的动力学曲线(说明书附图,图6)
NJUP1 10μM,HSA(0.5mg/mL)PBS缓冲液(pH 7.4,含5%二甲基亚砜)37℃孵育0-24h,激发波长为460nm,电压500V,狭缝5nm*5nm条件下用日立F-7000荧光分光光度计测其在574nm处荧光强度。如图6所示,NJUP1(10μM),HSA(0.5mg/mL)在1min内完全反应,并且荧光强度在24h以内保持稳定,表明NJUP1快速灵敏且荧光性能稳定,具有应用于临床前诊断的潜力。
实施例7探针NJUP1在水/二甲基亚砜混合溶液中随pH变化的荧光光谱测定(说明书附图,图7)
在激发波长为460nm下,电压500V,狭缝5nm*5nm条件下使用日立F-7000荧光分光光度计测定pH 3~14下的荧光强度变化。
如图7所示,NJUP1在水/二甲基亚砜混合溶液中随pH变化的荧光光谱图,其中NJUP1的浓度为10-6mol/L。随pH变化,探针分子荧光强度保持稳定,无明显变化。在HSA加入之后荧光从无到强的过程清晰可辨。pH 7~12的区间内始终保持很强的荧光强度。表明NJUP1是可以模拟生理环境用于胞内检测的荧光探针。
实施例8人人血清蛋白荧光探针的细胞毒性试验(说明书附图,图8)
将HeLa和LO2细胞分别加入到96孔板上,每个孔中大约有5×105个细胞,然后分别加入不同浓度的NJUP1,在37℃,5%CO2下孵育48h。孵育结束前4h在每个孔中加入20μL5mg/mL MTT,1200rcf离心5min,吸去上清液,每个孔中各加入200μL DMSO。在酶标仪上测定波长为490nm下的吸光度。每个浓度设三个重复,每次测定三次,然后计算细胞存活率。如图8所示,所述荧光探针具有较低的细胞毒性。
综上所述,本发明公开了一种人血清蛋白荧光探针及其制备方法和用途。该探针可通过简单化学原料制备,该荧光探针荧光强度高低与人血清蛋白含量成正比,可以用于定量检测人血清蛋白。通过该荧光探针对人血清蛋白的选择性实验数据,发现其对人血清蛋白响应远远高于其它小分子化合物,因此可广泛应用于样品中人血清蛋白的检测。
图1为人血清蛋白荧光检测原理示意图;
图2为本发明实施案例2中人血清蛋白荧光探针与人血清蛋白的紫外可见吸收光谱图;
图3为本发明实施案例3中人血清蛋白荧光探针与不同浓度的人血清蛋白反应的荧光发射光谱图;
图4为本发明实施案例4中荧光探针与阴离子,金属离子,各种氨基酸反应后荧光强度变化图;
图5为本发明实施案例5中人血清蛋白荧光探针与人血清蛋白及其它结构性质类似的化合物反应的荧光强度的曲线图;
图6为本发明实施例6中人血清蛋白荧光探针与HSA随时间变化荧光强度变化的动力学曲线图;
图7为本发明实施例7中探针NJUP1在水/二甲基亚砜混合溶液中随pH变化的荧光光谱测定图;
图8为本发明实施例8中人血清蛋白荧光探针的细胞毒性试验图。
Claims (3)
2.一种制备权利要求1中所述人血清蛋白荧光探针的方法,它由下列步骤组成:
步骤1.将2.5g的4-N,N-二甲基苯胺18.4mmol溶解在33mL 6M HCl溶液中,加入3.0mL巴豆醛6.8mmol在室温下搅拌1h,然后加入甲苯35mL,反应加热115℃回流过夜,TLC检测反应进行程度,冷却到室温后,除去甲苯层,加入饱和氢氧化钠溶液中和水层,用二氯甲烷萃取溶液,饱和NaCl溶液洗涤两次,无水硫酸钠干燥,过滤,减压浓缩,粗品经硅胶柱层析PE∶EA=4∶1v/v纯化,得到第一步产物N,N,2-三甲基喹啉-6-苯胺;
步骤2.将1.3g二氧化硒11.52mmol溶解在二噁烷40mL/水/4mL混合溶剂中,在80℃下加热30min,加入1.7g第一步产物N,N,2-三甲基喹啉-6-苯胺9.6mmol,80℃下搅拌4h,TLC检测反应进行程度,将混合物冷却至室温后,通过硅藻土过滤,然后通过少量二氯甲烷将滤渣多次冲洗,滤液在减压下浓缩,得到的粗品经硅胶柱层析PE∶EA=6∶1v/v纯化,得到第二步产物6-(二甲氨基)喹啉-2-甲醛;
步骤3.将100mg第二步产物6-(二甲氨基)喹啉-2-甲醛0.5mmol溶解在6mL无水乙醇中,加入67mg 2-硫代-2,4-噻唑烷二酮0.5mmol,45mg尿素0.75mmol,加热回流4h,TLC检测反应进行程度,冷却反应混合物,过滤,用冷无水乙醇清洗,无水乙醇重结晶,烘干,得到目标化合物。
3.权利要求1所述的人血清蛋白荧光探针在非治疗或诊断目的体外检测或胞内检测中的应用。
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