CN110194951A - 四苯乙烯衍生物荧光探针及其制备方法 - Google Patents
四苯乙烯衍生物荧光探针及其制备方法 Download PDFInfo
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- CN110194951A CN110194951A CN201910428885.8A CN201910428885A CN110194951A CN 110194951 A CN110194951 A CN 110194951A CN 201910428885 A CN201910428885 A CN 201910428885A CN 110194951 A CN110194951 A CN 110194951A
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- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- Luminescent Compositions (AREA)
Abstract
本发明公开了一种四苯乙烯衍生物荧光探针及其制备方法,以双溴取代二甲基TPE为主体合成化合物M2,用咪唑取代双溴制成化合物M3;通过孤对电子的配位键将化合物M3与Zn离子络合得到目标产物M4。化合物M3具有包覆阿霉素进行药物运输的能力,目标产物M4作为荧光探针与某些有机爆炸物能发生荧光猝灭,其中与对硝基苯酚的响应最为明显,故可以作为爆炸物荧光检测探针。
Description
技术领域
本发明属于聚集诱导发光荧光材料领域,具体涉及一种咪唑修饰的四苯乙烯衍生物荧光材料及其制备方法。
背景技术
虽然现代医学技术和诊断方法水平有了显着提高,但癌症的发病率和死亡率仍居高不下,并且有逐年增加的趋势,这严重威胁着人类的健康和生命。因此,开发用于癌症诊断和治疗的新探针以及开发用于癌症诊断和治疗的新原理和新方法对于提高癌症和肿瘤的治愈率以及患者的生存治疗具有重要意义。如今,纳米材料材料的使用是最有前途的癌症治疗技术之一。此外,纳米材料在体内的吸收,分布,代谢和排泄的原位实时监测已成为纳米材料在癌症治疗中治疗效果评估的关键问题。因此,提供允许刺激性诊断和治疗的多功能平台的纳米材料的应用成为最受欢迎的癌症治疗技术,即治疗诊断技术。治疗诊断学结合诊断(光学,计算机断层扫描(CT),磁共振(MR),后电子发射计算机断层扫描(PET)等)和治疗(光动力疗法(PDT),光热疗法(PTT)和基因疗法等)。
在与诊断平台兼容的所有纳米材料中,荧光团具有很高的灵敏度,简单性,高时间分辨率,快速响应性和可操作性,因此非常有应用潜力。常见的荧光团包括已广泛使用的香豆素和罗丹明等。然而,这些荧光团仍然具有很大的缺点,当这种荧光分子与被检测物质结合时,与被检测物质有很强的分子间作用力,分子之间形成严重的π-π堆积相互作用,促进非辐射途径释放能量,导致部分或完全猝灭的荧光。这种现象被称为聚集诱导荧光猝灭(ACQ)效应。这种效应导致无法用荧光追踪物质的分布。2001年,唐本忠团队发现某荧光团溶液在层压板上的紫外光下是不可见的,但是当溶剂蒸发时,样品在紫外光下清晰可见。这种现象与ACQ效应完全相反,唐将其命名为聚集诱导荧光效应(AIE)。自AIE效应发现以来,AIEgens已成为研究热点。已经合成并报道了许多具有AIE效应的荧光团,如四苯甲基硅烷(TPS),四苯乙烯(TPE)和六苯基硅油(HPS)等。凭借其独特的光学特性,具有AIE效应的物质不仅在感应化学物质,追踪细胞和靶向肿瘤方面,而且在用作药物输送系统方面都显示出巨大的潜力。通过特定的分子设计,AIE衍生物可以很好地用作药物递送的新型功能性载体或是检测探针,尤其是TPE衍生物,有很广泛的应用潜力。
例如在2014年Zhang及其同事报道了第一种带有响应性荧光的以TPE为载体的荧光材料,可用于对挥发性有机化合物(VOCs)的检测。这种是由基于TPE和4,4’-(2,2-二苯乙烯-1,1-二酰基)二苯甲酸以及N,N-二乙基甲酰胺中的Zn(NO3)2·6H2O构建的。合成的荧光材料对苯、甲苯、二甲苯和三甲苯等挥发性有机化合物表现出强烈的反应,即检测到VOCs时会产生荧光发射光谱的峰移。
Feng等人成功合成了一种TPE衍生物,该化合物可作为荧光传感器,能够在纳米级有选择性地、灵敏地识别2,4,6-三硝基苯酚(TNP)和2,4-二硝基苯酚(DNP)等芳香族硝基化合物。此外,该化合物对DNP具有较强的荧光衰减,为这些爆炸物的鉴别提供了一种实用的手段。
但以上四苯乙烯衍生物通常制备条件困难,而且部分难溶于水,这对四苯乙烯衍生物的实际应用产生了一定的影响。
发明内容
本发明的目的是提供一种咪唑取代的四苯乙烯衍生物荧光材料及其制备方法。
实现本发明目的的技术解决方案是:
一种四苯乙烯衍生物荧光探针(M4),所述探针通过孤对电子的配位键将化合物M3与Zn离子络合得到,其中,化合物M3具有如下结构:
本发明还提供了所述化合物M3的合成方法,包括如下步骤:在四氢呋喃体系下,以NaH为碱性试剂,将咪唑和化合物M2发生取代反应制备化合物M3的步骤;
优选的,咪唑与化合物M2的摩尔比为3:1,咪唑与NaH摩尔比为3:4,其具体制备步骤为:咪唑与NaH室温下搅拌15分钟,然后加入M2在室温下搅拌2小时,再将混合物缓慢加热至40℃,保持3小时。
本发明还提供了所述荧光探针即化合物M4的制备方法,包括如下步骤:将Zn(NO3)2·6H2O溶液与化合物M3的乙醇溶液在室温下搅拌一段时间后,再次加入乙醇,制得所述的探针。
优选的,Zn(NO3)2·6H2O与化合物M3的摩尔比为1:1。
优选的,室温下搅拌1分钟后,再次加入乙醇以稳定配合体系。
本发明还提供了目标产物四苯乙烯衍生物荧光探针作为具有AIE效应的荧光分子材料检测硝基苯酚爆炸物的应用。
本发明还提供了化合物M3作为药物载体包裹阿霉素药物的应用。
本发明与现有技术相比,其优点有:
(1)TPE衍生物荧光分子合成简单,可用于药物运输、物质检测方面,应用广泛。
(2)TPE衍生物荧光分子具有良好的水溶性,适用于人体水环境。
附图说明
图1为M3紫外吸收图谱。
图2为M4紫外吸收图谱。
图3为M3在330nm下的荧光发射图谱。
图4为M3在460nm下的荧光发射图谱。
图5为M3聚集诱导图。
图6为M4在强酸条件下释放图(330nm)。
图7为M4在强酸条件下释放图(460nm)。
图8为M4扫描电镜图。
图9为M4分子对于不同爆炸物的响应效果图。
具体实施方式
(一)本发明所述的探针即化合物M4的合成路线如下:
具体包括以下步骤:
步骤一:在氩气气氛下,量取四氢呋喃、4-甲基二苯甲酮、锌粉加入烧瓶,打开磁力搅拌器,并用保鲜膜封口,在-78℃下,将四氯化钛用注射器刺破保鲜膜加入烧瓶内,随后将反应混合物在室温下搅拌1.5h,然后在75℃加热回流12小时,即得M1。
步骤二:向三口烧瓶中加入四氯化碳、M1、N-溴代琥珀酰亚胺和过氧化苯甲酰,85℃加热回流10小时,即得M2。
步骤三:向三口烧瓶中加入咪唑的四氢呋喃溶液和氢化钠溶液,在室温下搅拌15分钟。然后将M2加入混合物中,在室温下搅拌2小时后,将混合物缓慢加热至40℃并保持搅拌3小时,即得M3。
步骤四:向洁净的三口烧瓶中加入M3的乙醇溶液,在室温下搅拌并加入六水硝酸锌的水溶液,搅拌1分钟后加入乙醇得稳定的化合物M4。
实施例1:四苯乙烯衍生物荧光探针的合成
1.化合物M1的合成
取洁净的500mL三口烧瓶,多次抽真空,在氩气保护下向三口烧瓶中加入4-甲基二苯甲酮(19.6g,0.1mol)、锌粉(20g,0.308mol),再在三口烧瓶中加入300mL四氢呋喃,打开磁力搅拌器搅拌,用保鲜膜封住一个烧瓶口,并用橡皮筋扎紧。向乙醇浴中缓慢倒入液氮以冷却,当冷却到-78℃时,量取20mL四氯化钛4,吸入注射器内,刺破保鲜膜缓慢均匀地加入烧瓶内,同时持续倒入液氮保持反应温度。加料完成后在球形冷凝管上套上气球,搅拌反应1.5h,气球适时放气。搅拌反应1.5h后换油浴75℃加热回流12h。TLC跟踪反应,在反应完成后,将反应混合物冷却至室温,加入盐酸溶液以除去未反应的锌粉,然后用二氯甲烷萃取多次。收集有机层,用无水硫酸钠干燥两小时,并过滤,滤饼用二氯甲烷多次冲洗,得到微黄色透明澄清溶液。用旋转蒸发仪浓缩溶液,拌硅胶,使用石油醚作为洗脱剂,通过柱色谱纯化,得到白色固体化合物,即M1(11.2g,0.031mol),产率为60%。
1H NMR(400MHz,CDCl3):7.81(d,2H),7.74(d,2H),7.54(t,1H),7.08(m,10H),6.90(m,8H),2.23(d,6H)).
13C NMR(100MHz,CDCl3,d):144.1,140.9,140.4,135.8,131.3,131.1,128.4,127.5,126.2,21.2.
2.化合物M2的合成
取洁净的250mL三口烧瓶,多次抽真空,在氩气保护下向三口烧瓶中加入称量好的M1(4.337g,0.012mol),N-溴代琥珀酰亚胺(3.56g,0.02mol)和过氧化苯甲酰(0.16g,0.6mmol),打开磁力搅拌器,油浴温度设置为85℃,回流反应10h。TLC跟踪反应进程,当其中M1不再减少时进行下一步操作。
点板检查上述反应情况,产物点为黄绿色荧光点。将反应液冷却至室温,过滤,加去离子水萃取多次,取油相用无水硫酸钠干燥2h并过滤。所得溶液在旋转蒸发仪上除去溶剂,拌硅胶。湿法上样,用展开剂(PE)对其进行柱层析分离,纯化过程中逐渐加入二氯甲烷调整极性,得到白色固体,即得M2,收率34.78%(2.17g,4.174mmol)。
1H NMR(300MHz,CDCl3,δ):7.10(m,10H),6.98(m,8H),4.40(m,4H).
13C NMR(75MHz,CDCl3,d):144.3,143.7,141.3,136.3,132.1,131.8,128.9,128.3,127.2,34.0.
3.化合物M3的合成
向洁净的250mL三口烧瓶中加入咪唑(0.204g,0.003mol)的四氢呋喃(THF)溶液,并加入氢化钠(0.096g,0.004mol)作碱性试剂。将混合物在室温下搅拌15分钟,然后将M2(0.482g,0.001mol)加入反应液中,并在室温下搅拌2小时。室温搅拌反应两小时后将混合物缓慢加热至40℃,继续搅拌反应3小时。TCL跟踪反应进程。
上述反应体系用去离子水和二氯甲烷洗涤四氢呋喃层多次,取二氯甲烷层,用无水硫酸钠干燥两小时并过滤,滤饼用二氯甲烷多次洗涤。所得溶液在旋转蒸发仪上除去溶剂,拌硅胶。湿法上样,用展开剂(PE)对其进行柱层析分离,得白色固体,即得M3,(0.206g,0.419mmol),产率41.88%。
1H NMR(400MHz,CDCl3):6.99(m,10H),5.02(s,4H),7.49(t,2H),7.12(td,8H),7.07(t,2H),6.86(d,2H)
4.化合物M4的合成
向洁净的100mL烧瓶中加入M3(246mg,0.5mmol)的乙醇溶液(25mL),在室温下搅拌并加入六水硝酸锌(150mg,0.5mmol)的水溶液(5mL),以制造Zn(M3)球,观察到立刻生成白色固体沉淀。继续搅拌1分钟后,加入50mL乙醇到反应混合物中以稳定球体。然后通过离心纯化得到M4球体,并用乙醇洗涤多次,并收集得白色固体颗粒。
实施例2:M3作为药物载体包裹阿霉素
先将阿霉素(DOX)溶解于M3(246mg,0.5mmol)的乙醇溶液(25mL)中(3.3×10-3M),在室温下加入六水硝酸锌(150mg,0.5mmol)的水溶液(5mL),在室温下剧烈搅拌,得DOX/Zn(M3)球。通过离心纯化得到的包覆的金属-有机系统,并用乙醇洗涤多次,得红色固体。将包覆的颗粒再分散在乙醇或磷酸盐缓冲液中以获得相应的胶体。
实施例3:紫外吸收光谱测定
(1)目标产物M3分子的紫外吸收光谱测定
用移液枪吸取2mL M3分子的待测液(0.01mmol/L)转移至4mL的比色皿中。预设紫外吸收波长范围确定在200nm至600nm之间,先做空白试验以此来扣除所用溶剂的空白干扰,最后再进行紫外吸收光谱测定。得到图1,即为M3分子的紫外吸收光谱。
(2)目标产物M4分子的紫外吸收光谱测定
用移液枪吸取2mL M3分子的待测液(0.05mg/mL)转移至4mL的比色皿中。预设紫外吸收波长范围确定在200nm至600nm之间,先做空白试验以此来扣除所用溶剂的空白干扰,最后再进行紫外吸收光谱测定。得到图2,即为M4分子的紫外吸收光谱。
对比图1和图2可知,M3分子的紫外最大吸光波长在310nm左右,而M4分子紫外最大吸光波长在315nm左右。
实施例4:荧光发射光谱测定
(1)M3的荧光发射图
用移液枪吸取3mL M3待测液(0.01mmol/L)转移至4mL的石英比色皿中,根据紫外吸收光谱,反扫荧光仪确定最大激发波长,在最大激发波长条件下激发,来测定不同溶剂配比下M3分子的荧光发射谱图。得到图3,即为M3分子的330nm荧光发射图。得到图4,即为M3分子的460nm荧光发射图。
(2)M3的聚集诱导图
用移液枪依次吸取3mL M3水和乙醇比例9:1-1:9为待测液转移至4mL的石英比色皿中,根据紫外吸收光谱,反扫荧光仪确定最大激发波长,在最大激发波长条件下激发,来测定不同溶剂配比下M3分子的荧光发射谱图。得到图5,即为M3分子的聚集诱导图。
(3)M4的荧光发射图
用移液枪吸取3mL M4待测液(0.01mmol/L)转移至4mL的石英比色皿中,根据紫外吸收光谱,反扫荧光仪确定最大激发波长,在最大激发波长条件下激发,来测定不同溶剂配比下M4分子的荧光发射谱图。
(4)M4的荧光释放图(强酸条件下)
用移液枪吸取3mL M4待测液(0.01mmol/L)转移至4mL的石英比色皿中,在强酸条件下,来测定不同时间下M4分子的荧光发射谱图。得到图6,即为M4分子的330nm,pH=4时的药物释放荧光发射图。得到图7,即为M4分子的460nm,pH=4时的药物释放荧光发射图。
通过观察图5,可以发现M3分子在乙醇/H2O=1:9时的荧光强度最大,且发生了最大发射波长的偏移,证明在该溶剂配比情况下,发生了聚集诱导荧光效应,且实验表明M3分子在470nm出现较大的发射波长。符合聚集诱导探针的要求,所以我们选取乙醇/H2O=1:9作为后续实验条件。
对比图6、图7可知,M4分子在酸性条件下荧光强度增强,说明在酸性条件下药物得到释放。
实施例5:M4扫描电镜测定
SEM电镜图显示M4分子是表面呈簇状聚集的球状分子,微球成球性好,直径大小约为7μm,颗粒性较好。得到图8,即为M4分子的扫描电镜图。
实施例6:对于不同爆炸物的检测
分别将爆炸物环三亚甲基三硝胺(RDX)、六硝基六氮杂异伍兹烷(CL-20)、对硝基苯酚、三硝基苯酚、环四亚甲基四硝胺(HMX)配制成浓度均为0.5mmol×L-1的溶液,分别装于5支试管中,编号1-5。在试管6中加入适量溶剂石油醚。剪下宽约1cm的滤纸条若干条浸泡于制备的Zn(M3)胶体中约1分钟。然后分别在1-6号试管中放入浸泡过胶体的纸条对应编号A-F,即刻取出,用吹风机吹干纸条,于356nm检测仪下观察纸条A-E以及空白对照纸条F的荧光猝灭情况。得到图9,即为M4分子对不同爆炸物检测情况图。
对比图9中纸条的荧光猝灭情况,我们可以发现,对于不同的爆炸物,M4的荧光猝灭情况不同,其中对于对硝基苯酚荧光几乎完全猝灭,说明M4对于对硝基苯酚的响应最为明显,M4具有作为对硝基苯酚检测荧光探针的潜力。
Claims (10)
1.一种四苯乙烯衍生物荧光探针,其特征在于,所述探针通过孤对电子的配位键将化合物M3与Zn离子络合得到,其中,化合物M3具有如下结构:
2.化合物M3,其特征在于,具有如下结构:
3.化合物M3的合成方法,其特征在于,包括在四氢呋喃体系下,以NaH为碱性试剂,将咪唑和化合物M2发生取代反应制备化合物M3的步骤;
4.如权利要求3所述的方法,其特征在于,咪唑与化合物M2的摩尔比为3:1。
5.如权利要求3所述的方法,其特征在于,咪唑与NaH摩尔比为3:4。
6.如权利要求1所述的四苯乙烯衍生物荧光探针的制备方法,其特征在于,将Zn(NO3)2·6H2O溶液与化合物M3的乙醇溶液在室温下搅拌一段时间后,再次加入乙醇,制得所述的探针。
7.如权利要求6所述的方法,其特征在于,Zn(NO3)2·6H2O与化合物M3的摩尔比为1:1。
8.如权利要求6所述的方法,其特征在于,室温下搅拌1分钟后,再次加入乙醇。
9.如权利要求1所述的四苯乙烯衍生物荧光探针作为具有聚集诱导荧光效应的荧光分子材料检测硝基苯酚爆炸物的应用。
10.如权利要求2所述的化合物M3作为药物载体包裹阿霉素药物的应用。
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