CN110857309B - 一种可激活型光热治疗试剂及其制备方法和应用 - Google Patents
一种可激活型光热治疗试剂及其制备方法和应用 Download PDFInfo
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Abstract
本发明属于精准医学领域中的诊疗试剂开发技术领域,涉及一种可激活型光热治疗试剂及其制备方法和应用。肿瘤标记物硫化氢可特异性的与所述可激活型光热治疗试剂作用,生成在近红外区有强吸收的染料,且具有近红外二区发光的特性。近红外光照条件下,新生成的材料可有效的将光能转化为热能,从而实现热消融肿瘤的目的。
Description
技术领域
本发明属于精准医学领域中的诊疗试剂开发,涉及一种肿瘤热疗试剂,具体涉及一种通过与肿瘤中富含的硫化氢反应生成光热材料,光照条件下实现热消融肿瘤目的相关材料的制备以及应用。
背景技术
肿瘤是一种常见病和多发病,已成为人类的主要致死疾病之一。发展有效的肿瘤诊断及治疗方法具有非常重要的意义。
研究表明肿瘤标志物介导的癌症精准检测及治疗是一种可靠新手段,具有独特的作用。在已发现多种标志物中,硫化氢在多种肿瘤过表达,是癌症诊疗的新靶点。通过设计合成对硫化氢能够选择性作用的智能材料,可以为肿瘤疾病诊断和治疗提供新的思路。本发明创新性的设计合成了基于氟硼二吡咯(BODIPY)荧光染料的智能型材料。癌细胞中过表达的硫化氢可特异性的与BODIPY中氯原子发生芳香亲核取代反应,导致硫取代的BODIPY的生成,从而在近红外区有强的吸收以及在近红外二区发光。近红外光光照下,新生成的材料有效的将光能转化为热能,从而实现了硫化氢激活的近红外二区荧光介导的光疗。
本发明独创性的设计合成了一个能够与硫化氢作用的智能材料,根据硫化氢在肿瘤组织中过表达,实现特异性激活。
发明内容
为解决上述问题,本发明第一个目的是提供一种可激活型光热治疗试剂,可与硫化氢作用的材料。
本发明第二个目的是提供一种可激活型光热试剂的制备方法。
本发明第三个目的是提供一种通过肿瘤中过表达的硫化氢激活的光热试剂的具体用途。
本发明的技术方案如下:
本发明独创性的设计合成了一个能够与硫化氢反应的材料。
一种可激活型光热试剂,其特征在于,具有如下结构式:
根据本发明所述一种可激活型光热试剂,硫化氢的反应位点是BODIPY中的氯。
根据本发明所述一种可激活型光热试剂,通过双键与BODIPY相连的基团为强拉电子基。
根据本发明所述一种可激活型光热试剂,硫化氢可与氯发生芳香亲核取代反应,生成硫取代化合物:
本发明还提供一种可激活型光热试剂的用途在于硫化氢引使得材料在近红外区有强的吸收以及在近红外二区发光。近红外光光照下,新生成的材料有效的将光能转化为热能,从而实现了硫化氢激活的近红外二区荧光介导的光热消融肿瘤。
本发明还提供一种可激活型光热试剂的制备方法,基于BODIPY染料的,其合成路线为:
本发明适用于光热治疗肿瘤材料的研发,通过肿瘤中过表达硫化氢激活光热材料达到热消融肿瘤的目的。研究表明肿瘤标志物介导的癌症精准检测及治疗是一种可靠新手段,具有独特的作用。在已发现多种标志物中,硫化氢在多种肿瘤过表达,是癌症诊疗的新靶点。通过设计合成对硫化氢能够选择性作用的智能材料,可以为肿瘤疾病诊断和治疗提供新的思路。本发明创新性的设计合成了基于BODIPY荧光染料的智能型材料。癌细胞中过表达的硫化氢可特异性的与BODIPY中氯原子发生芳香亲核取代反应,导致硫取代的BODIPY的生成,从而在近红外区有强的吸收以及在近红外二区发光。近红外光光照下,新生成的材料有效的将光能转化为热能,从而实现了硫化氢激活的近红外二区荧光介导的光疗。因此本发明是基于根据胶质肿瘤中过表达的硫化氢,而构建的硫化氢可激活型光热材料,进而达到肿瘤检测与治疗。
本发明同现有技术相比,具有以下优点和有益效果:
(1)基于BODIPY染料的智能材料,具有易修饰、合成简单等特点。
(2)本发明是特异性靶向硫化氢的荧光材料;该荧光材料可用于肿瘤的诊断与治疗,具有实用强的特点。
附图说明
图1是可激活型光热试剂在硫化氢存在下吸收光谱(a),不同能量光照下温度变化情况(b),光热转换的硫化氢依赖性(c),荧光光谱(d)变化情况。
图2是可激活型光热试剂在硫化氢存在下的暗毒性与光毒性(a);细胞染色表明荧光材料在硫化氢存在下具有强的光毒性(b)。
图3是可激活型光热试剂在小鼠肿瘤部位、正常部位切光照条件下升温情况。(a)无药光照组;(b)正常部位加药光照组;(c)肿瘤部位加药光照组;(d)a-c的数据分析图。
图4是可激活型光热试剂的氢谱。
图5是可激活型光热试剂的高分辨率质谱。
具体实施方式
下面结合附图和实施例对本发明作进一步阐述,本领域技术人员应当理解,所述实施例仅用于示例,而不对本发明构成任何限制。
术语:
Absorption(a.u.)为吸收值。
FL intensity(a.u.)荧光强度。
Wavelength(nm)波长(纳米)。
Time(min)时间(分钟)
BODIPY染料为氟硼二吡咯(BODIPY)染料
化合物1的合成
将6-氨基-1-溴代正己烷(65mg,0.25mmol),三缩乙二醇单甲醚修饰的没食子酸(152mg,0.25mmol),2-(7-氧化苯并三氮唑)-N,N,N',N'-四甲基脲六氟磷酸酯(121.6mg,0.32mmol),二异丙基乙基胺(191mg,1.48mmol),溶于适当的DMF中,常温反应10小时,用水稀释,混合物用乙酸乙酯萃取,有机层用水和盐水洗涤,干燥,过滤,旋干上柱得微黄色油状产物(71.3mg,37%)。1H NMR(CDCl3,400MHz)δ7.09(s,2H),4.23–4.18(m,6H),3.86–3.83(t,4H),3.80–3.77(t,2H),3.73–3.70(m,6H),3.67–3.62(m,12H),3.55–3.53(m,6H),3.43–3.49(t,2H),3.38(m,11H),1.96–1.89(m,2H),1.70–1.63(m,4H),1.54–1.48(q,2H).13C NMR(100MHz,CDCl3)δ167.0,152.5,141.5,129.9,107.4,72.4,71.9,70.7,70.6,70.5,69.7,69.2,58.9,51.6,40.6,39.9,33.7,32.6,29.5,27.8.HRMS(m/z):Calcd for C34H60NO13Br[M+Na]+:792.3146,found:792.3135.
化合物2的合成
将化合物1(100mg,0.13mmol)与2,3,3-三甲基-3H-吲哚(62mg,0.39mmol)溶于乙腈中,升温至95度回流,TLC检测,反应完全后,降至室温,旋干溶剂,加入EA洗涤数次,抽干得暗红色粘稠产物(24mg,22%)。1H NMR(D2O,400MHz)δ7.64–7.62(d,1H),7.59–7.57(d,1H),7.50–7.43(m,2H),6.97(s,2H),4.38–4.34(t,2H),4.18–4.13(m,6H),3.84–3.81(m,4H),3.76–3.74(m,2H),3.67–3.64(m,6H),3.61–3.57(m,12H),3.54–3.50(m,8H),3.47–3.45(m,9H),3.23–3.25(m,12H),1.98(s,2H),1.88–1.83(m,2H)1.53–1.47(m,2H),1.43(s,6H),1.35–1.31(m,4H).13C NMR(100MHz,CDCl3)δ195.8,166.9,152.3,152.1,141.1,129.9,123.2,115.6,107.2,72.2,71.9,70.6,70.5,70.4,69.7,69.0,58.9,51.7,40.6,39.9,32.6,29.5,27.8,26.1,12.1.HRMS(m/z):Calcd for C45H73N2O13Br[M-Br]+:849.5134,found:849.5113.
化合物3的合成
将化合物2(84.8mg,0.1mmol),与BODIPY醛(合成过程参考文献Dalton Trans.,2012,41,831-838.)(38.6mg,0.1mmol)溶于适量无水乙醇中90度回流5个小时,旋干柱层析得黑色粘稠产物(DCM/CH3OH=20:1,39mg,30%)。1H NMR(CD3OD,400MHz)δ8.22–8.18(d,1H),7.77–7.75(m,2H),7.64–7.60(m,4H),7.47–7.44(q,2H),7.39–7.35(d,1H),7.20–7.14(m,4H),4.54–4.50(t,2H),4.24–4.17(m,6H),3.87–3.85(m,4H),3.83–3.79(m,2H),3.73–3.69(m,8H),3.66–3.61(m,18H),3.53–3.51(m,9H),3.38–3.36(m,12H),2.73(s,2H),2.53–2.46(m,2H),1.93–1.88(m,2H),1.82(s,6H),1.66–1.60(m,4H),1.53(s,6H),1.38–1.33(m,8H),1.12–1.08(t,3H).13C NMR(100MHz,CD3OD)δ182.9,177.7,153.8,149.1,142.3,142.2,130.6,130.3,124.1,120.0,72.9,71.8,71.7,71.5,71.4,70.8,70.1,59.1,49.2,48.8,48.4,33.1,30.8,30.5,27.4,23.8,14.4,14.1,12.9.HRMS(m/z):Calcd forC65H89N4O13ClF2BBr[M-Br]+:1217.6176,found:1217.6168.其结构确认见附图4(氢谱)和附图5(质谱)。
效果实施例:
由图一可以看出,本光热可激活型试剂对硫化氢具有特异性的响应,只有硫化氢存在下,该试剂才具有光热效应。
图二表明该光热试剂对富含硫化氢的肿瘤HCT116细胞具有高的光毒性和低的暗毒性,因此是一个很好的可激活型光热材料。
图三证实该光热试剂可在富含硫化氢的肿瘤部位选择性的被激活,因此在光照条件下,产生高温,因而可有效热消融肿瘤。
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