CN111533775B - 一种比率型亮氨酸氨基肽酶荧光探针及其制备方法和其在肝肿瘤细胞靶向成像中的应用 - Google Patents
一种比率型亮氨酸氨基肽酶荧光探针及其制备方法和其在肝肿瘤细胞靶向成像中的应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及荧光探针生物应用技术领域,特别涉及一种具有肝肿瘤细胞靶向能力的比率型亮氨酸氨基肽酶荧光探针及其制备方法和其在肝肿瘤细胞靶向成像中的应用。
背景技术
肝癌是常见的恶性肿瘤之一,具有病症早期症状不典型、病势发展迅速等特点,实现早期准确诊断可有效提高治愈率。亮氨酸氨基肽酶(LAP)作为一种重要的肝肿瘤标志物,广泛分布于人体组织中,其活性变化与肝肿瘤细胞的生长、***和迁移密切相关。目前,血液中的亮氨酸氨基肽酶活性变化是临床肝肿瘤早期诊断的参考指标之一。然而受非原位检测的制约,通过血液途径难以获得肝肿瘤细胞LAP活性变化的准确数据。因此,迫切需要开发一种原位、高效的肝肿瘤细胞LAP活性检测方法,为肝癌的早期诊断提供重要参考。
荧光成像技术具有原位检测、时空分辨率高等优势,已成为肿瘤标志物活性检测的有力工具,性能优良的荧光探针是这一技术成功应用的关键。基于LAP水解探针N-端亮氨酸酰胺键实现荧光响应的原理,国内外研究人员设计了大量小分子LAP荧光探针,尤其是近红外比率型LAP荧光探针的制备,为LAP活性检测提供了重要工具。然而,实现肝肿瘤细胞LAP活性的准确检测仍需解决荧光探针肝肿瘤细胞的靶向问题,目前有关具有肝肿瘤细胞靶向能力的LAP荧光探针尚未见报道。
发明内容
有鉴于此,本发明提出一种具有肝肿瘤细胞靶向能力的比率型亮氨酸氨基肽酶荧光探针;
本发明还提出一种具有肝肿瘤细胞靶向能力的比率型亮氨酸氨基肽酶荧光探针的制备方法;
本发明还提出具有肝肿瘤细胞靶向能力的比率型亮氨酸氨基肽酶荧光探针在肝肿瘤细胞靶向成像中的应用。
本发明的技术方案是:
本发明提供一种式III所示的比率型亮氨酸氨基肽酶荧光探针:
本发明还提供了一种比率型亮氨酸氨基肽酶荧光探针的制备方法。如图1所示,所述制备方法为:将化合物I,Fmoc-Leu-OH,二异丙基乙胺,1-乙基-(3-二甲基氨基丙基)碳酰二亚胺,1-羟基苯并***按照一定的摩尔比加入到二氯甲烷和DMF混合溶液(体积比1:1)中,25℃搅拌反应24h,反应液纯化得到化合物II;所述化合物I,Fmoc-Leu-OH,二异丙基乙胺,1-乙基-(3-二甲基氨基丙基)碳酰二亚胺,1-羟基苯并***摩尔比为0.5~1:2:2:2:2,优选为1:1.2:1.2:1.2:2;将化合物II,二甲胺四氢呋喃溶液按照一定比例加入到二氯甲烷溶液中,一定温度下反应1h,反应液经过纯化得到化合物III;所述化合物II,二甲胺四氢呋喃溶液按照摩尔比的比例为0.5~1.5:10,优选为1:8;反应温度优选25℃~35℃。
本发明还提供了一种比率型亮氨酸氨基肽酶荧光探针应用于肝肿瘤细胞亮氨酸氨基肽酶靶向成像:采用共聚焦激光扫描显微镜(CLSM)对式III荧光探针在HuH7和A549细胞荧光成像进行了研究。式III荧光探针(10μM)分别与HuH7和A549细胞共孵育30分钟后,获得荧光光谱成像,激发波长选择405nm。
相对于现有技术,本发明提供的比率型亮氨酸氨基肽酶荧光探针具有以下优点:
该比率型亮氨酸氨基肽酶荧光探针具有明显的比率计量型特点、水溶性好和可实现肝肿瘤细胞亮氨酸氨基肽酶靶向成像等优点。该荧光探针被成功应用于肝肿瘤细胞亮氨酸氨基肽酶靶向成像,并取得了较好的成像效果。
附图说明
图1为本发明的比率型亮氨酸氨基肽酶荧光探针的反应路线图。
图2为本发明的比率型亮氨酸氨基肽酶荧光探针(10μM)在pH为7.5条件下,加入0U/L和100U/L亮氨酸氨基肽酶浓度的荧光发射光谱图。
图3为本发明的比率型亮氨酸氨基肽酶荧光探针在pH为7.5条件下,不同亮氨酸氨基肽酶浓度中激发波长为375nm,发射波长为520nm处的荧光效果检测图。
图4为本发明的比率型亮氨酸氨基肽酶荧光探针式III对肝肿瘤细胞靶向荧光成像效果图。
具体实施方式
为更好地理解本发明,下面结合附图和实施例对本发明作进一步的说明,但是本发明要求保护的范围并不局限于实施例表述的范围。
实施例1:制备化合物II
将式I所示的化合物0.1mmol,Fmoc-Leu-OH 0.15mmol,二异丙基乙胺0.15mmol,1-乙基-(3-二甲基氨基丙基)碳酰二亚胺0.15mmol,1-羟基苯并***0.15mmol加入到二氯甲烷和DMF混合溶液100ml(体积比1:1),氮气保护,搅拌,25℃反应24h,反应结束后,减压除去反应溶剂,粗品经过柱层析分离,二氯甲烷:甲醇为10:1为流动相,得到式II所示化合物380mg。
1H NMR(400MHz,DMSO)δ8.93(dd,J=8.6,1.3Hz,1H),8.78(dd,J=4.0,1.5Hz,1H),8.54(s,1H),7.88(d,J=7.5Hz,2H),7.79(d,J=7.8Hz,1H),7.70(dd,J=7.4,3.0Hz,2H),7.61(d,J=8.0Hz,1H),7.54(dd,J=8.6,4.1Hz,1H),7.41(t,J=7.4Hz,2H),7.31(t,J=7.1Hz,2H),7.27–7.23(m,1H),7.20–7.11(m,1H),6.94(d,J=8.0Hz,1H),6.20(s,2H),5.76(s,2H),5.60(d,J=9.2Hz,1H),5.42(d,J=5.9Hz,1H),5.22(d,J=5.6Hz,1H),4.99(d,J=5.5Hz,1H),4.30–4.25(m,2H),4.14(d,J=5.2Hz,1H),4.04–3.99(m,2H),3.81(d,J=4.4Hz,1H),3.71–3.58(m,1H),2.30(s,1H),1.17(t,J=7.1Hz,2H),0.77(dd,J=16.7,6.5Hz,6H).13C NMR(101MHz,DMSO)δ173.32,170.79,156.51,147.35,146.55,146.13,144.26,144.16,141.16,137.80,137.60,134.37,129.35,128.84,128.66,128.08,127.49,126.45,125.77,125.69,122.25,121.55,120.55,114.10,108.60,88.47,75.59,73.73,69.53,69.12,66.05,55.35,52.68,47.10,24.55,21.75,21.21.
实施例2:制备化合物II
将式I所示的化合物0.1mmol,Fmoc-Leu-OH 0.12mmol,二异丙基乙胺0.12mmol,1-乙基-(3-二甲基氨基丙基)碳酰二亚胺0.12mmol,1-羟基苯并***0.12mmol加入到二氯甲烷和DMF混合溶液100ml(体积比1:1),氮气保护,搅拌,25℃反应24h,反应结束后,减压除去反应溶剂,粗品经过柱层析分离,二氯甲烷:甲醇为10:1为流动相,得到式II所示化合物396mg。
实施例3:制备化合物III
将化合物II所示的化合物0.1mmol,二甲胺四氢呋喃溶液0.5mmol加入到30ml二氯甲烷溶液中,50℃反应1h,反应结束后,减压除去反应溶剂,粗品经过柱层析分离,二氯甲烷:甲醇为8:1为流动相,得到式III所示化合物320mg。
1H NMR(400MHz,DMSO)δ8.95(d,J=8.6Hz,1H),8.80(d,J=2.8Hz,1H),8.57(s,1H),8.37(s,2H),7.63(d,J=8.0Hz,1H),7.57(dd,J=8.6,4.0Hz,1H),6.96(d,J=8.0Hz,1H),5.62(d,J=9.2Hz,1H),4.50(dd,J=11.5,8.7Hz,2H),4.20–1.16(m,4H),3.97(s,2H),3.86(d,J=2.8Hz,1H),3.68(dd,J=9.4,3.1Hz,1H),1.79(d,J=18.1Hz,1H),1.60–1.41(m,2H),0.75(dd,J=18.8,6.3Hz,6H).13C NMR(101MHz,DMSO)δ170.50,147.42,146.56,145.83,137.60,134.42,128.81,126.44,122.28,121.48,114.36,108.90,88.49,75.37,73.67,69.52,69.04,65.66,51.00,24.02,22.63,22.05.HRMS(ESI)calcd for[III+H]+C23H32N6O6 487.2300,found 487.2315,[III+Na]+C23H31N6O6Na509.2125,found 509.2132.
实施例4:制备化合物III
将化合物II所示的化合物0.1mmol,二甲胺四氢呋喃溶液0.8mmol加入到30ml二氯甲烷溶液中,30℃反应1h,反应结束后,减压除去反应溶剂,粗品经过柱层析分离,二氯甲烷:甲醇为8:1为流动相,得到式III所示化合物410mg。
实施例5:荧光探针式III,在pH为7.5条件下加入浓度为0U/L和100U/L亮氨酸氨基肽酶的发射光谱测定。
准确称取实施例4中制备的荧光探针III,用二甲基亚砜配置成浓度为10mM的荧光探针母液,使用移液器吸取1μL加入到磷酸缓冲液和DMSO的混合溶液中(体积为1mL,体积比为9:1),此时荧光探针浓度为10μM。其中一个里面加入1μL亮氨酸氨基肽酶母液,使反应体系中亮氨酸氨基肽酶浓度为100U/L。为另一个设置空白对照,37℃下反应5分钟,激发波长为375nm,测定两个混合液的荧光发射光谱,结果见图2。荧光探针III与亮氨酸氨基肽酶反应前在432nm出现强的荧光发射峰,与亮氨酸氨基肽酶反应后,在520nm出现强的荧光发射峰,表现出明显的比率型探针特点。
实施例6:荧光探针式III,在pH为7.5,激发波长为375nm的条件下加入不同浓度的亮氨酸氨基肽酶的荧光检测效果。
准确称取实施例4中制备的荧光探针III,用二甲基亚砜配置成浓度为10mM的荧光探针母液,使用移液器吸取1μL加入到磷酸缓冲液和DMSO的混合溶液(体积为1mL,体积比为9:1),此时溶液中荧光探针浓度为10μM,分别加入1μL不同浓度亮氨酸氨基肽酶母液(最终亮氨酸氨基肽酶在反应体系中的浓度分别为0U/L、20U/L、40U/L、60U/L、100U/L),37℃条件下反应5min,测定其荧光强度值。激发波长为375nm,发射波长为520nm,荧光强度见图3,所述结果表明,该荧光探针检测亮氨酸氨基肽酶浓度与荧光强度呈现良好线性关系。
实施例7:荧光探针式III对肝肿瘤细胞靶向成像效果
准确称取实施例4中制备的荧光探针III,用二甲基亚砜配置成浓度为10mM的荧光探针母液,使用移液器吸取1μL加入到磷酸缓冲液和DMSO的混合溶液中(体积为1mL,体积比为9:1)。将荧光探针III(10μM)分别与肝肿瘤细胞株HuH7和非小细胞肺癌细胞株A549共同孵化,采用共聚焦激光扫描显微镜对式III荧光探针在HuH7和A549细胞荧光成像,激发波长选择405nm,获得2min和30min时的荧光成像图。如图4,荧光探针III表现出对肝肿瘤细胞株HuH7较好的靶向成像效果。
应当指出的是,在实施例7中采用非小细胞肺癌细胞株A549作为对照组仅为本发明的一种实施方式,在其他实施例中,当将荧光探针III(10μM)分别与肝肿瘤细胞株HuH7和其它肿瘤细胞株共同孵化时,最终得到的荧光成像图反映出荧光探针III同样会对肝肿瘤细胞株HuH7表现出较好的靶向成像效果。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (5)
3.如权利要求2所述的一种比率型亮氨酸氨基肽酶荧光探针的制备方法,其特征在于,步骤一中所述的摩尔比为1:1.2:1.2:1.2:2。
4.如权利要求2所述的一种比率型亮氨酸氨基肽酶荧光探针的制备方法,其特征在于,步骤二中所述的摩尔比为1:8。
5.如权利要求2所述的一种比率型亮氨酸氨基肽酶荧光探针的制备方法,其特征在于,步骤二中所述的温度为30℃。
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