CN106496103A - 一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物及其合成方法 - Google Patents
一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物及其合成方法 Download PDFInfo
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Abstract
本发明公开了一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物及其合成方法，其中具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物的结构式为：
Description
技术领域
本发明涉及一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物及其合成方法，可应用于生物学上活细胞双光子显微成像和磁共振成像双模式显影功能，具有明显的商业应用价值。
背景技术
磁共振成像(MRI)是一种较新的医学成像技术，用于医学诊断越来越受到人们的关注。1945年，以哈佛大学的E.M.Purcell和斯坦福大学的F.Bloch为首的两个研究小组几乎同时观察到核磁共振现象，他们两人因此获得1952年诺贝尔物理奖。1953年，美国Varian公司研制成功世界第一台商业化的核磁共振仪。随着造影剂的研究发展，人们对其应用的兴趣也突飞猛进。
磁共振成像可以提供高质量和高时空分辨率的软组织三维图像，而且具有无深度限制的组织渗透功能。1988年，第一个核磁造影剂——钆配合物被批准用于临床医学，目前以钆为主的配合物仍然是最常用的核磁共振成像探针。与其它诊断技术相比较，如X射线成像或正离子发射断层扫描(PET)，磁共振成像基于核磁共振光谱的原则没有电离辐射的危害。但是这项技术的缺点在于灵敏度低。众所周知，双光子荧光技术具有激发能量低、波长长、穿透性强、光损伤小且检测限低、灵敏度高等特点，在医疗诊断和荧光显微成像技术中有着不可限量的应用前景。因此相对于单独使用，结合这两种技术得到的图像可能获得更多的信息和细节。所以目前的发展趋势是研究双光子显微成像和磁共振成像双模式的造影剂用于医学诊断。
申请人对本申请的主题进行了如下的文献检索：
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发明内容
本发明旨在提供一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物及其合成方法，所要解决的技术问题是通过分子设计获得具有双光子显影和磁共振显影双功能的配合物。
Mn(Ⅱ)作为锰的一种重要的氧化态形式，其和各种配体所形成的功能配合物在光催化、磁共振显影和磁性材料等多个领域有着广泛的应用。基于以上考虑，本发明以具有优良光电性质的三苯胺作为给电子体(D)，以三联吡啶为电子受体(A)，并通过在三苯胺基团的末端引入不同辅助基团从而调节配合物水溶性与脂溶性以及产生协同推拉电子效应，设计合成了两种D-A构型的三苯胺-2,2':6',2"-三联吡啶新型Mn(Ⅱ)配合物Mn1，Mn2。
本发明双功能三苯胺三联吡啶锰配合物的结构式为：
本发明双功能三苯胺三联吡啶锰配合物的合成方法，包括如下步骤：
取0.400mmol配体L溶于20mL无水乙醇中置于50mL圆底烧瓶，加入含有0.200mmolMn(OAc)2·4H2O的20mL乙醇溶液，加热至回流反应4h，反应结束后反应液冷却至室温，随后向反应液中加入0.500mmol NH4PF6，继续加热至回流反应2h，析出红色固体，趁热过滤，收集滤饼，用无水乙醇重结晶，得目标产物，为红色固体。
所述配体L为配体L1或配体L2。
配体L1的结构式为：
配体L2的结构式为：
合成路线示意如下：
本发明配合物Mn1、Mn2的双光子显影和磁共振显影研究如下：
1、双光子显影
以HepG2为癌细胞模型，用10μmol/L的配合物Mn1和Mn2分别培养细胞1h，并和细胞质商染(ER tracker，488nm)、细胞核商染(Nuc-Red，633nm)进行共染。在760nm的波长下，通过双光子激光共聚焦显微镜观察，两种配合物都可以被细胞摄取，并均匀的分布在细胞质和细胞核内(图4)。
2、磁共振显影
用10μmol/L的配合物Mn1和Mn2分别培养HepG2细胞，之后离心使细胞沉降进行磁共振显影。和未加配合物的细胞(Control)相比，配合物加入后可以使显影快速且明显变亮(图5)，表明配合物具有靶向HepG2细胞的能力，具有造影增强功能。
本发明的有益效果体现在：
1、本发明合成的新型锰配合物Mn1和Mn2是一类具有细胞显影功能的双光子吸收材料。在760nm处具有较大的双光子吸收截面(图2)，激发能量低、穿透性强、光损伤小、光稳定性强、毒性低。
2、本发明配体中引入羟基，不仅使配合物的荧光增强，而且增加了配合物在极性溶剂中的溶解性，与文献报道相比配合物在极性溶剂中具有较长的荧光寿命(图3)，适用于活体细胞检测。
3、本发明的锰配合物既具有双光子显影功能(图4)又具有磁共振显影功能(图5)，可作为双模式的造影剂，与商用核磁造影剂Gd-DTPA相比，锰配合物能很好地被细胞摄取，使磁共振信号加强。
4、本发明的锰配合物，原料易得，成本低，反应条件温和，合成步骤简单，使其商业化成为可能。
附图说明
图1是配合物Mn2的晶体结构示意图，表明合成的锰配合物是尚未见报道且结构明确的新物质。
图2是配合物Mn1和Mn2在DMSO溶剂中的双光子吸收截面图，表明配合物在760nm处具有较大的双光子吸收截面。
图3是配合物Mn1(左)和Mn2(右)在不同溶剂中的荧光寿命光谱图，表明配合物具有高的荧光寿命，适用于活体细胞检测。
图4是配合物Mn1和Mn2在HepG2细胞摄取并分别和细胞质商染(ER tracker)、细胞核商染(Nuc-Red)双光子荧光共定位图。Mn1和Mn2信号与ER tracker、Nuc-Red均有重合，说明配合物可以被细胞摄取，并在细胞质和细胞核内均有分布。
图5是未加配合物的细胞与加入配合物Mn1，Mn2的细胞磁共振显影图，图中显示：加入配合物Mn1，Mn2的细胞比未加配合物的细胞磁共振显影明显加强(变亮)，表明配合物具有靶向HepG2细胞的能力，具有造影增强功能。
具体实施方式
实施例1：
取配体L1(0.202g,0.400mmol)溶于20mL无水乙醇中并置于50mL圆底烧瓶内，加入含有Mn(OAc)2·4H2O(0.049g,0.200mmol)的20mL乙醇溶液，加热至回流反应4h，反应结束后反应液冷却至室温，随后向反应液中加入NH4PF6(0.082g,0.500mmol)，继续加热至回流反应2h，析出红色固体，趁热过滤，减压过滤收集滤饼，用无水乙醇重结晶，得目标产物Mn10.206g，为红色固体，收率75.90％(按配体量计算，下同)。
M.P.:232℃.1H NMR(400MHz,d6-DMSO,ppm):δ8.72(d,J＝31.1Hz,12H),8.04(s,4H),7.86(s,4H),7.52(s,4H),7.34(s,8H),7.11(s,14H),5.15(s,2H),4.49(s,4H).IR(cm-1):3421(m),3063(m),2922(m),1587(vs),1512(s),1475(s),1417(m),1329(s),1288(m),1196(s),1017(m),844(s),792(s),760(m),698(m),658(m),640(m),558(s),522(m).ESI-MS:m/z(100％),534.50(100％).Anal.Calcd for C68H52F12MnN8O2P2:C,60.14；H,3.86；N,8.25.Found:C,60.39；H,3.88；N,8.28.
实施例2：
取配体L2(0.214g,0.400mmol)溶于20mL无水乙醇中并置于50mL圆底烧瓶内，加入含有Mn(OAc)2·4H2O(0.049g,0.200mmol)的20mL乙醇溶液，加热至回流反应4h，反应结束后反应液冷却至室温，随后向反应液中加入NH4PF6(0.082g,0.500mmol)，继续加热至回流反应2h，析出红色固体，趁热过滤，减压过滤收集滤饼，用无水乙醇重结晶，得目标产物Mn20.211g，为红色固体，收率74.45％(按配体量计算，下同)。
M.P.:236℃.1H NMR(400MHz,d6-DMSO,ppm):δ8.72(d,J＝30.9Hz,12H),8.03(s,4H),7.85(s,4H),7.52(s,4H),7.32(s,8H),7.09(s,13H),5.15(s,4H),4.49(s,8H).IR(cm-1):3393(m),3063(m),2922(m),2872(m),1593(vs),1510(s),1475(s),1417(m),1327(s),1288(m),1197(s),1016(s),844(vs),791(s),731(m),671(m),658(m),639(m),558(s),521(m).ESI-MS:m/z(100％),564.33(100％).Anal.Calcd for C70H56F12MnN8O4P2:C,59.29；H,3.98；N,7.90.Found:C,59.50；H,4.00；N,7.93.
本发明制备的配合物Mn1、Mn2的双光子显影和磁共振显影研究如下：
1、双光子显影
以HepG2为癌细胞模型，用10μmol/L的配合物Mn1和Mn2分别培养细胞1h，并和细胞质商染(ER tracker，488nm)、细胞核商染(Nuc-Red，633nm)进行共染。在760nm的波长下，通过双光子激光共聚焦显微镜观察，两种配合物都可以被细胞摄取，并均匀的分布在细胞质和细胞核内(图4)。
2、磁共振显影
用10μmol/L的配合物Mn1和Mn2分别培养HepG2细胞，之后离心使细胞沉降进行磁共振显影。和未加配合物的细胞(Control)相比，配合物加入后可以使显影快速且明显变亮(图5)，表明配合物具有靶向HepG2细胞的能力，具有造影增强功能。
Claims (2)
1.一种具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物，其特征在于其结构式为：
2.一种权利要求1所述的具有双光子显影和磁共振显影双功能的三苯胺三联吡啶锰配合物的制备方法，其特征在于包括如下步骤：
取0.400mmol配体L溶于20mL无水乙醇中置于50mL圆底烧瓶，加入含有0.200mmol Mn(OAc)2·4H2O的20mL乙醇溶液，加热至回流反应4h，反应结束后反应液冷却至室温，随后向反应液中加入0.500mmol NH4PF6，继续加热至回流反应2h，析出红色固体，趁热过滤，收集滤饼，用无水乙醇重结晶，得目标产物，为红色固体；
所述配体L为配体L1或配体L2；
配体L1的结构式为：
配体L2的结构式为：
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| CN111039853A (zh) * | 2019-12-26 | 2020-04-21 | 安徽大学 | 一种可用于光声成像和光热治疗的铁配合物及其制备方法和用途 |
| CN111039853B (zh) * | 2019-12-26 | 2023-02-14 | 安徽大学 | 一种可用于光声成像和光热治疗的铁配合物及其制备方法和用途 |
| CN113527364A (zh) * | 2021-05-28 | 2021-10-22 | 安徽大学 | 一种Mn(II)配合物多光子吸收材料及其制备方法和用途 |
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