CN113861160B - 一种一氧化碳气体检测化学发光探针、制备方法及其应用 - Google Patents
一种一氧化碳气体检测化学发光探针、制备方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种一氧化碳气体检测化学发光探针，该探针具有高选择性和高灵敏度。本发明的一氧化碳气体检测化学发光探针，其所述的探针是具有如式I结构所示的3‑(2‑(烯丙基醚)‑3‑氯‑4‑(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物：
Description
技术领域
本发明涉及一种探针、制备方法及应用，更具体地说涉及一种一氧化碳气体检测化学发光探针、制备方法及其应用。
背景技术
CO在冶金工业上是一种很好的还原剂，如工业还原氧化铁等，也可用作工业原料，如合成甲醇和光气等，还可用作气体燃料，如水煤气。同样，CO在生物方面也发挥很好的作用：它作为生命体重要的气体信使，被认为是一种多功能信号生物分子，在保护炎症、血管甚至癌症疾病方面具有显著的治疗潜力，在神经、心血管和免疫系统内发生的各种生理和病理生理过程中扮演重要的角色。以血红素降解为主要来源的内源性CO可激活胍环化酶活性，减轻氧化应激，抑制增生，扩张血管，可防止内皮细胞凋亡、高氧和缺血性肺损伤。而有多方面应用的CO在较高浓度下会对神经系统和心血管系统有毒性作用，它比氧气更容易与血红蛋白结合，会影响血液携带氧气的能力和组织缺氧，严重的会造成窒息。所以综合来看，对于CO的快速方便且灵敏清晰的检测是很迫切的。相比较传统的检测法，化学发光法是一种新颖的检测方式，具有快响应度、高选择性、低检测限等优点，此外，原位发射光子可以取代传统的激发光，可以有效地避免荧光技术中存在的背景自荧光，在成像中提供了极高的信噪比和灵敏度。目前已开发的检测CO的探针多为荧光探针，这些探针大多仍存在一些缺陷，如发射波长短、响应时间长、颜色或发射光谱的分辨率差、选择性适中、使用紫外光(<400nm)激发等。这些缺陷在很大程度上影响了探针的应用，所以开发一种检测CO的化学发光探针是十分有必要的
发明内容
本发明所要解决的技术问题是：克服现有技术存在的不足，提供一氧化碳气体检测化学发光探针，该探针具有高选择性和高灵敏度。
此外，本发明还提供该一氧化碳气体检测化学发光探针以及该探针检测一氧化碳及其含量中的应用。
本发明的技术构思和原理如下：该基于3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物探针在PdCl2的存在下可选择性与一氧化碳反应并发生产生540nm处的化学发光，且在0-25μM CORM-3溶液浓度范围内，540nm处的化学发光强度与CORM-3(一种释放一氧化碳的供体)溶液释放出来的CO浓度有着较好的线性关系。本发明首次制备3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物并首次将其用于气态CO的检测，从而解决了现有技术存在的问题。
本发明解决其技术问题的技术方案如下：
本发明的一氧化碳气体检测化学发光探针，其所述的探针是具有如式I结构所示的3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物：
本发明上述的一氧化碳气体检测化学发光探针的制备方法，其包括以下步骤：将3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯和和亚甲基蓝溶于冰浴下的二氯甲烷和甲醇混合溶液中，在黄光照射和氧气鼓泡条件下反应即生成3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物即为一氧化碳气体检测化学发光探针。
本发明上述的一氧化碳气体检测化学发光探针的制备方法，其进一步的技术方案是所述的所述的反应条件为：在氘灯黄光照射和氧气鼓泡下，反应4个小时以上；所述的混合溶液其二氯甲烷和甲醇的体积比1：1。再进一步的技术方案是所述的反应后进行纯化：将反应液减压浓缩，粗产物经过反相高效液相色谱分离，之后对固体真空干燥即得一氧化碳气体检测化学发光探针。更进一步的技术方案是所述的反相高效液相色谱分离的参数为90％乙腈、10％水、20min。
本发明的上述的探针可以在检测一氧化碳及其含量中进行应用。
本发明化学发光探针仅与一氧化碳发生化学发光反应，对其它Zn2+,Ca2+,Ni2+,Mg2 +,Hg2+,Cr3+,SO4 2-,NO2 -,Cl-,C2O4 2-,SCN-,H2PO4 -,F-,Br-,OH-,SO3 2-,Ser,Lys,Phe,Asn,Ala,Val,Thr,Glu,Arg,Asp等离子和氨基酸均无反应，具有很好的选择性和特异性。
本发明具有以下有益效果：
1)本发明化学发光探针与PdCl2在pH＝7.4的缓冲溶液没有光，在加入一氧化碳后，产生540nm处的化学发光；
2)采用本发明化学发光探针后，检测灵敏度高，对CORM-3的检测限可达到0.03μM；
3)本发明荧光探针在PdCl2存在下仅与一氧化碳发生化学发光反应，对其它离子均无反应，具有很好的选择性和特异性。具有适宜的化学发光发射波长(540nm)；
4)本发明化学发光探针制备工艺简单易行，易于规模化生产。
附图说明
图1为本发明实施例2探针在PdCl2存在下与各种离子反应的化学发光发射光谱
图2为本发明实施例2探针在PdCl2存在下与各种离子反应的化学发光变化图
图3为本发明实施例3探针在PdCl2存在下与一氧化碳反应的化学发光增量图
图4为本发明实施例3探针在PdCl2存在下对CORM-3浓度的化学发光强度工作曲线
图5为本发明实施例3探针在PdCl2存在下对0-25μM CORM-3浓度的化学发光强度线性关系图
图6为本发明实施例3探针液体在PdCl2存在下对一氧化碳气体的化学发光变化图
图7为本发明实施例3探针固体在PdCl2存在下对一氧化碳气体的化学发光变化图
图8为本发明实施例1制备的一氧化碳气体检测化学发光探针1H-NMR图
图9为本发明实施例1制备的一氧化碳气体检测化学发光探针高分辨质谱图
具体实施方式
下面参照附图并结合实施例对本发明作进一步详细描述。
实施例1制备一氧化碳气体检测化学发光探针
将214mg 3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯和少量亚甲基蓝溶于20ml的二氯甲烷和甲醇的混合溶液(体积比为1：1)中；在冰浴条件，氧气鼓泡和氘灯黄色光源照射下，剧烈搅拌4小时；反应结束后，先对反应液进行减压浓缩，然后用反相高效液相色谱(90％乙腈,10％水,20min)分离，最后真空干燥得到淡黄色固体184mg，即为一氧化碳气体检测化学发光探针纯品(1H-NMR图和高分辨质谱图见图8、图9)。所得荧光探针纯品实测分子量为460.17。
本实施例工艺路线如下：
实施例2一氧化碳气体检测化学发光探针与各种离子反应的光谱性质
称取13.8mg实施例1制得一氧化碳检测和线粒体定位的荧光探针，配成浓度为3mM的10mL DMSO溶液，作为探针母液。称取88.38mg CORM-3，配成30mM的10mL DMSO溶液，作为一氧化碳的供体溶液。称取10.64mg PdCl2，配成浓度为6mM的水溶液。
荧光光谱测试：将10μL探针母液，10μL氯化钯溶液加入到一定量的50mM PBS缓冲溶液(pH 7.4)中，然后分别加入各种离子：Zn2+,Ca2+,Ni2+,Mg2+,Hg2+,Cr3+,SO4 2-,NO2 -,Cl-,C2O4 2-,SCN-,H2PO4 -,F-,Br-,OH-,SO3 2-,Ser,Lys,Phe,Asn,Ala,Val,Thr,Glu,Arg,Asp，使离子终浓度为100μM，荧光探针终浓度为10μM。即时测试其荧光发射光谱。发射的狭缝宽度为10nm。所得结果如图1所示。将上述所配置溶液置于Tanon-5200Multi中，观察其化学发光变化，结果见图2，图(A)为白光下，图(B)为黑暗中。
以上结果表明：
(1)实施例1制得化学光探针本身与氯化钯在溶液中不发光，在加入一氧化碳的供体溶液后，该探针在540nm处出现强发射光。
(2)实施例1制得荧光探针对一氧化碳具有高度的选择性和特异性，并且在上述条件下，能够从Zn2+,Ca2+,Ni2+,Mg2+,Hg2+,Cr3+,SO4 2-,NO2 -,Cl-,C2O4 2-,SCN-,H2PO4 -,F-,Br-,OH-,SO3 2-,Ser,Lys,Phe,Asn,Ala,Val,Thr,Glu,Arg,Asp等常见离子和氨基酸中区分出CO。
实施例3一氧化碳气体检测化学发光探针与一氧化碳反应产物的光谱性质
将10μL实施例2中的探针母液和氯化钯溶液加入到一定量的50mM PBS缓冲溶液(pH7.4)中，然后加入不同当量的CORM-3溶液，使化学发光探针的终浓度为10μM，CORM-3最终浓度分别为0μM,10μM,30μM,50μM,70μM,100μM,150μM,200μM,300μM。CORM-3溶液加入后，即时测量其化学发光发射光谱。发射的狭缝宽度为10nm。所得化学发光强度的增量图见图3；以540nm处的化学发光强度数据制作工作曲线，结果见图4。
该实验结果表明，反应后化学发光强度随CO浓度的增加而增加；反应后化学发光强度与0-25μM范围内的金离子浓度呈线性关系，可以用于CO含量的定量分析检测,以540nm处的化学发光强度与0-25μM范围内的浓度线性关系曲线见图5。
实施例4一氧化碳气体检测化学发光探针对气体一氧化碳的检测
取探针母液10μL，PdCl2溶液10μL加入到50mM PBS缓冲溶液(pH 7.4)，此时探针的浓度为10μM，向探针系统中注入1mL CO气体，记录探针溶液的化学发光强度变化，如图6所示，图(A)表示白光状态下，图(B)表示黑暗状态下，图(C)表示(A)和(B)的定位复合图；图中右侧小瓶为注射CO的探针系统，左侧小瓶为探针系统对照样。将普通试纸在10μM探针溶液和20μM的PdCl2溶液中浸泡，然后自然风干，溶液为二氯甲烷和甲醇，液体体积为1：1。将风干的探针试纸放入小瓶中，随后往瓶中注射1mL CO气体，观察试纸的化学发光变化，如图7所示，图(A)表示白光状态下，图(B)表示黑暗状态下，图(C)表示(A)和(B)的定位复合图；图中右侧小瓶为注射CO的探针系统，左侧小瓶为探针系统对照样。
Claims (6)
1.一种一氧化碳气体检测化学发光探针，其特征在于，所述的探针是具有如式I结构所示的3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物：
2.一种如权利要求1所述的一氧化碳气体检测化学发光探针的制备方法，其特征在于，包括以下步骤：将如式II所述的物质和亚甲基蓝溶于冰浴下的二氯甲烷和甲醇混合溶液中，在黄光照射和氧气鼓泡条件下反应即生成3-(2-(烯丙基醚)-3-氯-4-(金刚烷(甲氧基)甲基)苯基)丙烯酸甲酯衍生物即为一氧化碳气体检测化学发光探针；
3.根据权利要求2所述的一氧化碳气体检测化学发光探针的制备方法，其特征在于，所述的反应条件为：在氘灯黄光照射和氧气鼓泡下，反应4个小时以上；所述的混合溶液其二氯甲烷和甲醇的体积比1：1。
4.根据权利要求3所述的一氧化碳气体检测化学发光探针的制备方法，其特征在于，反应后进行纯化：将反应液减压浓缩，粗产物经过反相高效液相色谱分离，之后对固体真空干燥即得一氧化碳气体检测化学发光探针。
5.根据权利要求4所述的一氧化碳气体检测化学发光探针的制备方法，其特征在于，所述的反相高效液相色谱分离的参数为90％乙腈、10％水、20min。
6.一种如权利要求1所述的探针在制备检测一氧化碳及其含量探针中的应用。
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