CN113527346A - 基于bodipy染料专一响应次氯酸的荧光探针、制备及应用 - Google Patents
基于bodipy染料专一响应次氯酸的荧光探针、制备及应用 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、光致发光和化学发光等方法。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。近年来,这些化学反应型的荧光探针主要基于以下几种机理:硫族元素的氧化,碳碳双键的断裂,酰肼的氧化,分子内环化等反应策略。尽管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(在紫外可见光区)且在生物体内成像应用匮乏等,所以构建对ClO‒具有高选择性的新型长波长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。因此,基于BODIPY荧光染料专一性响应生物细胞内ClO‒的长波长荧光探针,并实现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:C44H42BF2N4O3S+,命名为BDP-R-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保护冰水浴下,氢化钠加入到四氢呋喃溶剂中混合得到混合溶剂,将丙酮基对甲苯磺酸肟酯与6-甲氧基-1-萘满酮按照当量为1:(1-2)的比例溶于混合溶剂中,50℃反应3h,冰水淬灭,二氯甲烷萃取,柱层析分离得到化合物3;
(4)N2保护下,将化合物3与4-吡啶甲醛按照当量为1:(0.5-1)的比例溶于无水DCM中,加入一滴三氟乙酸,30℃过夜反应。再向反应体系加入当量为0.5的四氯苯醌搅拌30min,随后冰浴下加入当量为0.01的二异丙基乙胺和三氟化硼乙醚,室温搅拌3h。用饱和碳酸氢钠溶液水洗,二氯甲烷萃取,柱层析得到化合物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-R-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:
本发明基于BODIPY染料用于专一检测ClO‒的荧光探针,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。
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;
(2)本发明的检测方法可以实现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;
(3)本发明检测信号明显,为类近红外荧光增强型荧光探针。
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-R-ClO的核磁氢谱图。
图2为荧光探针BDP-R-ClO的核磁碳谱图。
图3为荧光探针BDP-R-ClO与ClO‒作用的时间紫外变化。
图4为荧光探针BDP-R-ClO与ClO‒作用的时间荧光变化。
图5为荧光探针BDP-R-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590 nm与ClO‒的浓度线性拟合图。
图7为常见氨基酸对探针BDP-R-ClO检测ClO‒的荧光选择性。
图8为常见氨基酸对探针BDP-R-ClO检测ClO‒的荧光干扰性。
图9为荧光探针BDP-R-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-R-ClO检测ClO‒的细胞毒性。
图11为荧光探针BDP-R-ClO检测ClO‒RAW264.7细胞成像图。
图12为荧光探针BDP-R-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
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1-2h,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保护冰水浴下,氢化钠加入到四氢呋喃溶剂中混合得到混合溶剂,将丙酮基对甲苯磺酸肟酯与6-甲氧基-1-萘满酮按照当量为1:1.2的比例溶于混合溶剂中,50℃反应3h,冰水淬灭,二氯甲烷萃取,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4-吡啶甲醛按照当量为1:0.5的比例溶于无水DCM中,加入一滴三氟乙酸,30℃过夜反应。再将当量为0.5的四氯苯醌加入反应体系搅拌30min,随后冰浴下加入当量分别为0.01的二异丙基乙胺和0.01三氟化硼乙醚,室温搅拌3h。用饱和碳酸氢钠溶液水洗,二氯甲烷萃取,柱层析得到化合物4;
1H NMR (400 MHz,CDCl3) δ 8.69 (t, J = 7.4 Hz, 4H), 7.29 (d, J = 5.5Hz, 2H), 6.88 (dd, J = 8.9, 2.5 Hz, 2H), 6.71 (d, J = 2.2 Hz, 2H), 3.78 (s,6H), 2.76 (t, J = 6.9 Hz, 4H), 2.43 (t, J = 6.9 Hz, 4H), 1.26 (s, 6H)。13C NMR(101 MHz, CDCl3) δ 160.67, 150.65, 150.48, 145.06, 143.09, 134.65, 133.84,132.40, 131.53, 130.64, 130.52, 130.40, 124.46, 121.33, 114.47, 114.18,112.34, 55.30, 30.82, 20.44, 12.71, 12.28.
(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-R-ClO。
1H NMR (500 MHz, DMSO-d6) δ 9.48 (s, 2H), 8.63 – 8.49 (m, 4H), 7.67 –7.56 (m, 2H), 7.29 – 7.12 (m, 2H), 7.07 – 6.92 (m, 4H), 6.02 (s, 2H), 3.85(s, 6H), 3.32 (s, 4H), 2.84 (s, 4H), 1.30 (s, 6H)。13C NMR (126 MHz, DMSO) δ186.50, 161.27, 154.92, 153.22, 150.72, 146.41, 144.06, 134.79, 132.42,132.26, 131.43, 131.16, 130.38, 130.29, 130.12, 129.99, 124.23, 120.59,114.71, 113.13, 63.58, 55.91, 43.34, 40.51, 40.34, 39.68, 39.51, 39.04,30.33, 20.20, 13.04.
实施例2
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1~2h,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保护冰水浴下,氢化钠加入到四氢呋喃溶剂中混合得到混合溶剂,将丙酮基对甲苯磺酸肟酯与6-甲氧基-1-萘满酮按照当量为1:1的比例溶于混合溶剂中,50℃反应3h,冰水淬灭,二氯甲烷萃取,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4-吡啶甲醛按照当量为1:0.8的比例溶于无水DCM中,加入一滴三氟乙酸,30℃过夜反应。再向反应体系加入当量为0.5四氯苯醌搅拌30min,随后冰浴下加入当量为0.01的二异丙基乙胺和三氟化硼乙,室温搅拌3h。二氯甲烷萃取,柱层析得到化合物4;
(5)BDP-R-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。
实施例3
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1-2h,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保护冰水浴下,氢化钠加入到四氢呋喃溶剂中混合得到混合溶剂,将丙酮基对甲苯磺酸肟酯与6-甲氧基-1-萘满酮按照当量为1:2的比例溶于混合溶剂中,50℃反应3h,冰水淬灭,二氯甲烷萃取,柱层析分离得到化合物3;
(4)化合物4的制备
N2保护下,将4-吡啶甲醛与化合物3按照当量为1:1的比例溶于无水DCM中,加入一滴三氟乙酸,30℃过夜反应。再向反应体系加入当量为0.5四氯苯醌搅拌30min,随后冰浴下加入当量为0.01的二异丙基乙胺,10min后当量为0.01加入三氟化硼乙醚,室温搅拌3h。用饱和碳酸氢钠溶液水洗,二氯甲烷萃取,柱层析得到化合物4;
(5)BDP-R-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。
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1 mM BDP-R-ClO的荧光探针储备液;探针BDP-R-ClO(10µM)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561nm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1nm的蓝移。同时,在荧光图谱上可观察到,在用560nm的激发下,661nm处出现一个荧光发射峰并增强约20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,661nm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661nm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 = 14.295 X + 32.247,线性相关系数R2= 0.993并计算出检测限为1.8 nM。(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-R-ClO 分别加入上述选择的活性氮以及活性氧化物分析物种(100 µM)后(0:Blank, 1:ClO-, 2:ONOO-, 3:H2O2 , 4:·OH-, 5:·OtBu,6:TBHP , 7:O2·- , 8:1O2 , 9:NO , 10:NO2 -, 11:Hcy ,12:GSH, 13:Cys, 14:HS-, 15:SO4 2-, 16:SO3 2-, 17:Ca2+, 18:Mg2+, 19:Cu2+,探针BDP-R-ClO可以对ClO-进行专一性识别,并在661nm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-R-ClO(10 µM)在分别加入上述分析物(0:Blank , 1:ONOO-, 2:H2O2, 3:·OH-, 4:·OtBu, 5:TBHP , 6:O2·- , 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+)后再加入100 µM 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-R-ClO溶于二甲基亚砜中得到10mM探针母液,配置pH为5.0、5.5、6.0、6.5、7.0、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661 nm处荧光逐渐增强,且在pH值为7.2-8.0的生理范围内,荧光强度依然更强。实验证明探针BDP-R-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-R-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(0,1.25,2.5,5,10,20 μM)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RAW264.7细胞内ClO‒的检测性能测试
检测ClO‒的荧光探针BDP-R-ClO对小鼠单核巨噬细胞(RAW264.7)细胞中ClO‒的荧光共聚焦成像。结果如图11所示,(a)空白组;(b) DM-BDP-OCl (10 μM)孵育30分钟;(c)先与脂多糖(LPS, 1.0 μg/mL)孵育16 h,随后用佛波醇-12-肉豆蔻酸-13-乙酸酯(PMA, 1.0μg/mL)孵育60 min,最后与BDP-R-ClO (10μM)孵育30 min;(d) 4-氨基苯甲酸肼(ABAH,200 μM)预孵育60 min;(e,f,h,g)分别为明场图像和(a,b,c,d)的叠加图像,(λex=560 nm,λem= 600-700 nm)。通过共聚焦红色通道观察,检测ClO‒的荧光探针在RAW264.7细胞中产生明亮的红色荧光;对照组实验中,细胞与BDP-R-ClO共同孵育,由成像实验结果可以观察红色通道荧光响应微弱。由此说明探针可以检测细胞内源性ClO‒。该结果也表明,本发明的荧光探针具有检测RAW264.7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ClO‒的检测性能测试
通过小鼠腹部腹腔注射方式将NaClO(5. eq)注射到小鼠右侧腹部,10min后在原处注射BDP-R-ClO(25 μL DMSO,1 mM);将生理盐水和BDP-R-ClO注射到裸鼠左侧腹部作为对照组。注射后0min、10min、20min、30min、40min进行成像系统内荧光监测,通过共聚焦红色通道观察,检测ClO‒的荧光探针在加入NaClO的小鼠腹腔中产生明亮的红色荧光;对照组实验中,仅用生理盐水和探针孵育的右腹成像实验结果中可以观察红色通道荧光响应微弱。由此说明探针可以快速地原位监测小鼠活体内源性ClO‒的产生。
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,冰浴加入二异丙基乙胺,随后加入N,N-二甲氨基硫代甲酰氯,搅拌,50℃反应24h,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,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,将丙酮基对甲苯磺酸肟酯与6-甲氧基-1-萘满酮溶于混合溶剂中,50℃反应2~3h,冰水淬灭,二氯甲烷萃取,柱层析分离得到化合物3;
(4)N2保护下,将化合物3与4-吡啶甲醛溶于无水DCM中,加入一滴三氟乙酸,30℃过夜;再向反应体系加入四氯苯醌,随后冰浴下加入二异丙基乙胺和三氟化硼乙醚,室温搅拌2~3h;用饱和碳酸氢钠溶液水洗,二氯甲烷萃取,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,120℃回流,重结晶得到探针BDP-R-ClO。
7.根据权利要求2所述的制备方法,其特征在于:所述步骤(5)中化合物2和化合物4按照当量为1:(2-3)比例添加,加热搅拌48h。
9.权利要求9所述的荧光探针在专一性检测ClO-试剂中的应用。
10.根据权利要求9所述的应用,其特征在于:所述荧光探针的检测限为1.8 nM。
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