CN116425785A - 基于bodipy专一响应次氯酸的荧光探针、制备方法及应用 - Google Patents
基于bodipy专一响应次氯酸的荧光探针、制备方法及应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及荧光探针领域,具体涉及一种基于BODIPY染料专一响应次氯酸的荧光探针、制备方法及应用。
背景技术
次氯酸(HClO)作为重要的弱酸性生物活性氧(ROS),在生物体内由H2O2和Cl-在髓过氧化物酶(MPO)的催化下产生。生物体中一定浓度的HClO/ClO-在保持细胞正常生理功能、细胞信号转导、维持内环境稳态以及免疫防御系统中发挥着重要的作用。然而过量的HClO/ClO-会导致细胞凋亡和组织损伤,进一步增加阿尔茨海默病、神经退行性疾病、糖尿病、心血管疾病、风湿性关节炎和癌症等疾病的发生风险。因此,快速、灵敏的检测方法对于识别检测环境和生命体内的HClO/ClO-具有重要意义。
迄今为止,已经探索出了多种方法用于ClO-的检测,其中包括电化学分析、免疫组织化学、荧光探针法等等。在这些方法中荧光探针法具有响应速度快,灵敏度高,可原位成像和生物创伤性低等优点,在化学分析、生物分析以及医学研究中得到了广泛的应用。尽管目前已报道的荧光探针实现了对ClO-的检测,但是仍然存在一些问题,例如选择性低(某些ClO-探针也可能对H2O2和ONOO-产生响应),荧光发射波长较短(没有达到近红外区),在生物体内成像应用匮乏等,因此构建对ClO-具有高选择性的新型近红外荧光探针并实现对细胞和活体成像的研究仍迫在眉睫。BODIPY作为一种优良的荧光团,由于其光稳定性好、高摩尔吸收、高荧光量子产率以及对环境因素的耐受性强,近年来被引入到各种探针中,获得了良好的荧光效果。专利CN106749364A公开了一种检测次氯酸根离子的荧光分子探针,该探针为BODIPY衍生物,其检测原理是通过次氯酸根的氧化作用使C=N键会氧化断裂并且生成新的C=O键,该探针的发射波长为521nm,最强吸收峰在508nm处,该波长处于可见光区,而可见光区的组织穿透区浅,在检测的过程中易受可见光的影响,而产生检测误差;而发射波长在近红外区的荧光探针则可以大大避免可见光的干扰,因此,构建基于BODIPY荧光染料专一性响应生物细胞内ClO-的新型近红外荧光探针,并实现探针在活体层面的应用具有重要意义。
发明内容
本发明提出了一种基于BODIPY染料专一响应次氯酸的荧光探针、制备方法及应用,该探针制备方法操作方便,原料易得,能够实现细胞以及小鼠活体内ClO-的专一性检测。
实现本发明的技术方案是:
一种基于BODIPY染料专一响应ClO-的荧光探针,化学分子式为:C40H38BF2N4OS3 +,命名为BDP-ENE-ClO,探针的结构式为:
所述的荧光探针的制备方法,步骤如下:
(1)N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,冰水浴中加入二异丙基乙胺,N,N-二甲氨基硫代甲酰氯按照当量1:(1-2)的比例加入,搅拌,50℃反应24h,二氯甲烷萃取,柱层析分离得到化合物1;
(2)步骤(1)制得的化合物1溶于二氯甲烷中,三溴化磷按照当量为1:(1-2)的比例加入,室温搅拌1-2h,加水淬灭,二氯甲烷萃取,柱层析分离得到化合物2;
(3)N2保护下,2,4-二甲基吡咯、4-吡啶甲醛按照当量为1:(0.5-1)溶于二氯甲烷中,加入当量为0.1的三氟乙酸,室温过夜;再向反应体系下加入当量为0.5的四氯苯醌,搅拌30min,冰浴下加入当量为2-3的三乙胺和当量为3-4的三氟化硼乙醚,室温下反应3h;柱层析分离得到化合物3;
(4)N2保护下,将化合物3与5-甲基-2-噻吩甲醛按照当量为1:(3-4)的比例溶于乙醇中,加入当量为10的哌啶,80℃回流4-5h;旋干反应液,柱层析分离得到化合物4。
(5)将化合物2和化合物4按照当量为1:(2-3)的比例溶于甲苯,120℃回流48h,重结晶得到探针BDP-ENE-ClO。
本发明制备的荧光探针在制备细胞/活体中在专一检测ClO-试剂中的应用。
荧光探针的合成路线如下:
用二甲基亚砜(DMSO)配制1mM BDP-R-ClO的荧光探针储备液;探针BDP-ENE-ClO(5μM)与待测溶液在溶液体系为乙腈/PBS缓冲液(1:1,v/v,10mM,pH=7.4)中进行反应,在荧光图谱上可观察到,在用630nm的激发下,690nm处出现一个荧光发射峰并增强约40倍,表面待测溶液中含有ClO-,若没有出现荧光发射峰则表示没有。
进行定量检测时,记录荧光图谱上690nm处的荧光峰代入线性回归方程为:Y=0.60904X+0.62648,线性相关系数R2=0.998,该线性方程以ClO-浓度为横坐标,探针在690nm处的荧光强度为纵坐标。
检测机制是N,N-二甲氨基硫代甲酸酯基团被次氯酸氧化离去,引起电子转移,酚盐进一步发生自消除反应释放出荧光团,从而引起荧光信号变化。
本发明的有益效果是:
1、本发明一种利用BODIPY染料专一性检测ClO-的荧光探针,合成方法简单,操作方便;可以实现ClO-专一性检测,而且不受其他活性氮和活性氧化物类的干扰;该探针在溶液测试中,利用紫外和荧光光谱可判断出探针与ClO-反应时间,浓度依赖性关系;在通过选择性和抗干扰能力测试观察出,探针可专一性检测ClO-,不与活性氧化物反应且抗干扰能力强;并且探针的pH稳定性强,细胞毒性小。还可通过荧光成像技术达到对Hela细胞和小鼠活体中的ClO-检测的目的。
2、本发明探针的检测信号明显,为类近红外荧光增强型荧光探针。上述探针检测ClO-时不受其他活性氮和活性氧类物质的干扰,操作过程简便、快速、灵敏,检测限为49nM。更重要的是探针的发射达到了690nm,可以有效检测到细胞和活体中的ClO-,在生物监测领域具有良好应用前景。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1为荧光探针BDP-ENE-ClO的核磁氢谱图。
图2为荧光探针BDP-ENE-ClO的核磁碳谱图。
图3为荧光探针BDP-ENE-ClO与ClO-作用的时间紫外变化。
图4为荧光探针BDP-ENE-ClO与ClO-作用的时间荧光变化。
图5为荧光探针BDP-ENE-ClO测定ClO-的浓度滴定实验荧光变化。
图6为荧光最强发射波长690nm与ClO-的浓度线性拟合图。
图7为常见阴离子、阳离子和氨基酸对探针BDP-ENE-ClO检测ClO-的荧光选择性。
图8为常见阴离子、阳离子和氨基酸对探针BDP-ENE-ClO检测ClO-的荧光干扰性。
图9为荧光探针BDP-ENE-ClO和探针加ClO-在不同pH缓冲溶液中最大荧光强度变化图。
图10为探针BDP-ENE-ClO检测ClO-的细胞毒性。
图11为荧光探针BDP-ENE-ClO检测ClO-RAW264.7细胞成像图。
图12为荧光探针BDP-ENE-ClO检测ClO-小鼠活体成像。
具体实施方式
下面将结合本发明实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
荧光探针的制备步骤如下:
(1)化合物1的制备
N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,冰水浴中加入二异丙基乙胺,N,N-二甲氨基硫代甲酰氯按照当量1:1的比例加入,50℃加热反应24h,二氯甲烷萃取,柱层析分离得到化合物1;
(2)化合物2的制备
步骤(1)制得的化合物1溶于二氯甲烷中,三溴化磷按照当量为1:1.2的比例加入,室温搅拌1h,加水淬灭,二氯甲烷萃取,柱层析分离得到化合物2;
(3)化合物3的制备
N2保护下,2,4-二甲基吡咯、4-吡啶甲醛按照当量为1:0.5的比例溶于二氯甲烷中,加入当量为0.1的三氟乙酸,室温过夜;再向反应体系下加入当量为0.5的四氯苯醌,搅拌30min,冰浴下加入当量为2.4的三乙胺和当量为3.6的三氟化硼乙醚,室温下反应3h;柱层析分离得到化合物3;
(4)化合物4的制备
N2保护下,将化合物3与5-甲基-2-噻吩甲醛按照当量为1:4的比例溶于乙醇中,加入当量为10的哌啶,80℃回流4-5h;旋干反应液,柱层析分离得到化合物4。
1H NMR(400MHz,DMSO-d6)δ8.81–8.77(m,2H),7.73(s,1H),7.69(s,1H),7.59–7.55(m,2H),7.17(d,J=3.6Hz,2H),7.14(s,1H),7.10(s,1H),6.95(s,2H),6.87(dd,J=3.6,1.2Hz,2H),2.52(s,6H),1.24(s,6H).13C NMR(125MHz,CDCl3)δ151.73,149.48,142.93,141.94,139.88,139.37,132.30,131.33,128.74,128.00,125.48,122.99,117.10,116.17,28.68,14.89,13.83.
(5)BDP-R-ClO的制备
将化合物2和化合物4按照当量为1:2的比例溶于甲苯,120℃回流48h,重结晶得到探针BDP-ENE-ClO。
1H NMR(500MHz,DMSO-d6)δ9.45(s,2H),8.53(s,2H),7.76(d,J=15.7Hz,2H),7.58(s,2H),7.23–7.09(m,6H),7.01(s,2H),6.89(s,2H),5.99(s,2H),3.29(s,6H),2.52(s,6H),1.40(s,6H).13C NMR(125MHz,DMSO)δ186.48,154.89,153.08,146.36,143.94,141.07,140.10,132.19,132.10,131.65,131.55,130.32,129.94,127.96,124.21,119.73,63.57,43.32,39.02,16.04,15.46.
实施例2
荧光探针的制备步骤如下:
(1)化合物1的制备
N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,冰水浴中加入二异丙基乙胺,N,N-二甲氨基硫代甲酰氯按照当量1:2的比例加入,50℃加热反应24h,二氯甲烷萃取,柱层析分离得到化合物1;
(2)化合物2的制备
步骤(1)制得的化合物1溶于二氯甲烷中,三溴化磷按照当量为1:1的比例加入,室温搅拌2h,加水淬灭,二氯甲烷萃取,柱层析分离得到化合物2;
(3)化合物3的制备
N2保护下,2,4-二甲基吡咯、4-吡啶甲醛按照当量为1:0.5的比例溶于二氯甲烷中,加入当量为0.1的三氟乙酸,室温过夜;再向反应体系下加入当量为0.5的四氯苯醌,搅拌30min,冰浴下加入当量为3的三乙胺和当量为4的三氟化硼乙醚,室温下反应3h;柱层析分离得到化合物3;
(4)化合物4的制备
N2保护下,将化合物3与5-甲基-2-噻吩甲醛按照当量为1:3的比例溶于甲苯中,加入当量为10的哌啶,80℃回流5h;旋干反应液,柱层析分离得到化合物4。
(5)BDP-ENE-ClO的制备
将化合物2和化合物4按照当量为1:3的比例溶于甲苯,120℃回流48h,重结晶得到探针BDP-ENE-ClO。
实施例3
荧光探针的制备步骤如下:
(1)化合物1的制备
N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,N,N-二甲氨基硫代甲酰氯按照当量1:1.5的比例加入,冰水浴中加入二异丙基乙胺,50℃加热反应24h,二氯甲烷萃取,柱层析分离得到化合物1;
(2)化合物2的制备
步骤(1)制得的化合物1溶于二氯甲烷中,三溴化磷按照当量为1:2的比例加入,加碱后室温搅拌1.5h加水淬灭,二氯甲烷萃取,柱层析分离得到化合物2;
(3)化合物3的制备
N2保护下,2,4-二甲基吡咯、4-吡啶甲醛按照当量为1:0.5的比例溶于二氯甲烷中,加入当量为0.1的三氟乙酸,室温过夜;再向反应体系下加入当量为0.5的四氯苯醌,搅拌30min,冰浴下加入当量为2的三乙胺和当量为4的三氟化硼乙醚,室温下反应3h;柱层析分离得到化合物3;
(4)化合物4的制备
N2保护下,将化合物3与5-甲基-2-噻吩甲醛按照当量为1:4的比例溶于乙腈中,加入当量为10的哌啶,80℃回流4.5h;旋干反应液,柱层析分离得到化合物4。
(5)BDP-ENE-ClO的制备
将化合物2和化合物4按照当量为1:2.5的比例溶于甲苯,120℃回流48h,重结晶得到探针BDP-R-ClO。
实施例4
荧光探针的制备步骤如下:
(1)化合物1的制备
N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,N,N-二甲氨基硫代甲酰氯按照当量1:1.5的比例加入,冰水浴中加入二异丙基乙胺,50℃加热反应24h,二氯甲烷萃取,柱层析分离得到化合物1;
(2)化合物2的制备
步骤(1)制得的化合物1溶于二氯甲烷中,三溴化磷按照当量为1:2的比例加入,加碱后室温搅拌1.5h加水淬灭,二氯甲烷萃取,柱层析分离得到化合物2;
(3)化合物3的制备
N2保护下,2,4-二甲基吡咯、4-吡啶甲醛按照当量为1:0.8的比例溶于二氯甲烷中,加入当量为0.1的三氟乙酸,室温过夜;再向反应体系下加入当量为0.5的四氯苯醌,搅拌30min,冰浴下加入当量为2.5的三乙胺和当量为3.5的三氟化硼乙醚,室温下反应3h;柱层析分离得到化合物3;
(4)化合物4的制备
N2保护下,将化合物3与5-甲基-2-噻吩甲醛按照当量为1:3.5的比例溶于乙腈中,加入当量为10的哌啶,80℃回流4.5h;旋干反应液,柱层析分离得到化合物4。
(5)BDP-ENE-ClO的制备
将化合物2和化合物4按照当量为1:3的比例溶于甲苯,120℃回流48h,重结晶得到探针BDP-R-ClO。
实施效果例
利用实施例1中的探针进行性能测试
(1)溶液中检测ClO-的荧光探针BDP-R-ClO的反应时间测试
用二甲基亚砜(DMSO)配制1mM BDP-R-ClO的荧光探针储备液;探针BDP-ENE-ClO(5μM)与ClO-(100μM)在溶液体系为乙腈/PBS缓冲液(1:1,v/v,10mM,pH=7.4)中进行反应,如图3所示,从紫外吸收图谱观察BDP-R-ClO在683nm处的吸收峰在加入ClO-后下降并有微弱蓝移,随后保持不变;反应前后的吸收峰发生了4nm的蓝移。同时,在荧光图谱上可观察到,在用630nm的激发下,690nm处出现一个荧光发射峰并增强约40倍(图4所示)。
(2)溶液中检测ClO-的荧光探针BDP-R-ClO的浓度滴定测试以及浓度线性关系
在浓度滴定实验中,发现随着ClO-的浓度逐渐增加,690nm处的荧光峰也逐渐增强,其荧光强度在ClO-浓度至100μM时达到最大。(见图5所示)。
以ClO-浓度为横坐标,探针BDP-R-ClO在690nm处的荧光强度为纵坐标,绘制图并进行线性拟合,得到该探针的线性回归方程为:Y=0.60904X+0.62648,线性相关系数R2=0.998并计算出检测限为49nM。(见图6所示)。
(3)干扰性和抗干扰性离子实验
在不同的荧光比色皿中,分别加入4mL乙腈/PBS缓冲液(1:1,v/v,pH=7.4)和40μL荧光探针储备液,如图7所示,当探针BDP-ENE-ClO分别加入上述选择的活性氮以及活性氧化物分析物种(100μM)后(0:Blank,1:ClO-,2:ONOO-,3:H2O2,4:OH-,5:OtBu,6:TBHP,7:1O2,8:NO,9:NO2 -,10:Hcy,11:GSH,12:Cys,13:HS-,14:SO4 2-,15:SO3 2-,16:Ca2+,17:Mg2+,18:Cu2+,探针BDP-ENE-ClO可以对ClO-进行专一性识别,并在690nm处出现明显的红色荧光,而与其它种类分析物反应后没有荧光出现,因此,探针可以实现专一性响应ClO-。当BDP-ENE-ClO(5μM)在分别加入上述分析物(0:Blank,1:ONOO-,2:H2O2,3:OH-,4:OtBu,5:TBHP,6:1O2,7:NO,8:NO2 -,9:Hcy,10:GSH,11:Cys,12:HS-,13:SO4 2-,14:SO3 2-,15:Ca2+,16:Mg2+,17:Cu2+)后再加入100μM ClO-反应10分钟后,可以看出ClO-在与各种分析物共存情况下,BDP-R-ClO在复杂的溶液体系内依然能够专一性检测到ClO-。实验证明,BDP-R-ClO能够在响应ClO-时不受其它物质的干扰(见图8所示)。
(4)pH值的响应性实验
将探针BDP-ENE-ClO溶于二甲基亚砜中得到1mM探针母液,配置pH为5.0、5.5、6.0、6.5、7.0、7.4、7.5、8.0的溶液,对探针以及探针和ClO-反应后荧光强度的变化进行了研究。
结果如图9所示,探针荧光强度在pH值为5.0-8.0的溶液中基本保持不变;加入ClO-后,在pH值为5.0-6.0的溶液中荧光强度几乎不变,在pH值为6.0-8.0的溶液中,其位于690nm处荧光逐渐增强,且在pH值为7.2-8.0的生理范围内,荧光强度更强。实验证明探针BDP-ENE-ClO能够适应生物体内的pH环境。
(5)MTT细胞毒性实验
利用探针BDP-ENE-ClO对HeLa细胞的MTT细胞毒性实验,结果如图10所示。HeLa细胞用含有不同浓度的探针(0,2,5,10,20,30,40μM)培养液孵育后,计算细胞的存活百分比。结果如图10所示,低浓度下细胞存活率可高达90%,探针几乎没有细胞毒性。
(6)检测ClO-的荧光探针对Hela细胞内ClO-的检测性能测试
检测ClO-的荧光探针BDP-ENE-ClO对宫颈癌细胞(Hela)细胞中ClO-的荧光共聚焦成像。结果如图11所示,(a)空白组;(b)先与ClO-孵育30分钟,再与BDP-ENE-ClO孵育2h;(c)先与H2O2孵育30分钟,再与BDP-ENE-ClO孵育2h;(d)先与SIN-1孵育30分钟,再与BDP-ENE-ClO孵育2h(λex=630nm,λem=650-720nm)。通过共聚焦红色通道观察,检测ClO-的荧光探针在Hela细胞中产生明亮的红色荧光,而在其他分析物的细胞组可以观察到红色通道的荧光响应微弱,几乎没有荧光。由此说明探针可以选择性检测细胞外源性的ClO-。该结果也表明,本发明的荧光探针具有检测Hela细胞内ClO-的良好应用前景。
(7)检测ClO-的荧光探针对小鼠活体内外源性ClO-的检测性能测试
荧光探针BDP-ENE-ClO对活体内外源性次氯酸小鼠荧光成像。小鼠被分为两组,(a)空白组;(b)实验组。通过小鼠腹部腹腔注射方式将(a)生理盐水,(b)NaClO(1mM,100μL)分别注射到小鼠腹部,10min后在原处注射BDP-ENE-ClO(100μM,200μL)。注射后10min、30min、60min进行成像系统内荧光监测,通过小动物活体成像仪观察到,在实验组中,小鼠体内产生明亮的红色荧光并随时间的延长而逐渐增加,而空白组荧光相对较弱,同时荧光强度几乎不变。由此说明探针可以快速地原位监测小鼠活体外源性ClO-。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
2.权利要求1所述的基于BODIPY染料专一响应次氯酸的荧光探针的制备方法,其特征在于,步骤如下:
(1)N2保护下,将对羟基苯甲醇溶于1,2-二氯乙烷中,冰浴条件下加入二异丙基乙胺,随后再加入N,N-二甲氨基硫代甲酰氯,搅拌条件下加热反应至完全,反应溶液经二氯甲烷萃取、柱层析分离得到化合物1;
(2)N2保护下,将步骤(1)制得的化合物1溶于二氯甲烷中,加入三溴化磷,室温搅拌反应至完全,用冰水淬灭、二氯甲烷萃取、柱层析分离得到化合物2;
(3)N2保护冰水浴下,将2,4-二甲基吡咯和4-吡啶甲醛溶于无水DCM中,加入三氟乙酸,室温反应过夜;再向反应体系加入四氯苯醌搅拌,随后在冰浴条件下加入三乙胺和三氟化硼乙醚,室温搅拌,经柱层析得到化合物3;
(4)N2保护下,将化合物3和5-甲基-2-噻吩甲醛溶于乙醇中,加入哌啶,加热回流反应后旋干反应液,经柱层析得到化合物4;
(5)将化合物2和化合物4溶于甲苯中,回流反应,用DCM和PE重结晶得到探针BDP-ENE-ClO。
7.根据权利要求2所述的基于BODIPY染料专一响应次氯酸的荧光探针的制备方法,其特征在于:所述步骤(5)中化合物2和化合物4的反应当量为1:(2-3),回流反应的温度为48h。
8.权利要求1所述的荧光探针在制备专一性检测ClO-试剂中的应用。
9.根据权利要求8所述的应用,其特征在于,步骤为:以二甲基亚砜为溶剂配制荧光探针储备液,然后与待测溶液在乙腈/PBS缓冲液体系中进行反应,从荧光图谱中观察荧光探针在690nm处的吸收峰在加入待测溶液后的变化,进而对ClO-进行定性判断;然后记录在690nm处的荧光强度,代入线性方程,计算待测溶液中ClO-的浓度。
10.根据权利要求9所述的应用,其特征在于:所述荧光探针储备液的浓度为1mM,乙腈/PBS缓冲液的浓度为10mM,pH=7.4,其中乙腈和PBS的体积比为1:1;线性方程为Y=0.60904X+0.62648,R2=0.998。
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