CN108659115B - 一种血型抗原三糖a类似物bsa衍生物的合成方法及应用 - Google Patents
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Abstract
本发明提供了一种血型抗原三糖A类似物BSA衍生物的合成方法,包含以下步骤:(1)Cu催化血型抗原三糖A类似物与端位连接羧基的叠氮化物环加成反应生成中间产物1,4‑二取代‑1,2,‑三唑化合物;(2)步骤(1)中环加成产物与BSA发生偶联反应合成免疫偶联物;本发明还涉及血型抗原三糖A类似物BSA衍生物在血液检测、交叉配血等方面的临床应用。本发明合成血型抗原三糖A类似物BSA衍生物的反应步骤简单,反应条件温和,所得产物收率较高;同时,本发明合成的产品血型抗原三糖A类似物BSA衍生物在血液检测、交叉配血等方面的具有重要的生物学应用价值。
Description
技术领域
本发明属于化学合成与医药技术领域,具体涉及一种血型抗原三糖A类似物BSA衍生物的合成方法及应用。
背景技术
人体血液根据红细胞膜表面抗原的不同可分为不同的血型。不同血型的血液中具有不同的抗原和抗体。A型血的红细胞上带有A抗原,血清中有B抗体;B型血的红细胞上带有B抗原,血清中有A抗体;AB型血的红细胞上既有A抗原也有B抗原,血清中没有其抗体;O型血的红细胞上A抗原和B抗原都没有,血清中相应的抗体同时存在。这就使不同血型的血液相互输血时,因为抗原和抗体的凝聚作用而发生溶血现象,进而可能危及人的生命安全。
血型抗原是由糖蛋白和糖脂组成,而血型抗原和抗体的特异性识别主要是通过血型抗原上的糖链进行识别。血型抗原三糖是血型抗原的特异性所在,血型抗原A的主要特征是糖链终末端的N-乙酰半乳糖胺。
研究发现,血型抗原A及其类似物有望用于制备抗器官移植排斥、抗输血排斥的免疫抑制药物和医疗器械以及制备血液疾病相关的检测试剂,同时,血型抗原A及其类似物与牛血清蛋白交联的免疫偶联物在血液检测、交叉配血等方面也具有潜在的生物学和临床应用。因此,发展一种通用、合成步骤简单并且收率较高的方法来合成血型抗原A类似物BSA衍生物在化学合成及生物医药方面具有非常重要的意义。
发明内容
本发明的目的是提供一种合成血型抗原三糖A类似物BSA衍生物的新方法和这种血型抗原三糖A类似物BSA衍生物的应用。
本发明的目的是这样实现的:一种血型抗原三糖A类似物BSA 衍生物的合成方法,产物血型抗原A交联的蛋白质(式Ⅰ)
是通过以下步骤合成的:
(1)Cu催化血型抗原三糖A类似物与端位连接羧基的叠氮化物环加成反应生成中间产物1,4-二取代-1,2,-三唑化合物,
(2)步骤(1)中环加成产物与BSA发生偶联反应合成免疫偶联物。
进一步地,所述的步骤(1)的环加成反应的催化剂为CuSO4/Na ascorbate催化体系。
进一步地,所述的步骤(2)的偶联反应的溶剂为pH值为5.0~6.3 的PBS缓冲溶液。
进一步地,所述的步骤(2)的偶联反应中用EDC作为羧基活化剂。
本发明的血型抗原三糖A类似物BSA衍生物在血液检测、交叉配血等方面的生物学和临床应用。
同现有技术相比,本发明从血型抗原三糖A类似物出发,通过和端位连接羧基的叠氮化物环加成,然后羧基与蛋白质氨基反应合成免疫偶联物,反应步骤简单,反应条件温和,所得产物收率较高;同时,本发明的血型抗原三糖A类似物BSA衍生物在血液检测、交叉配血等方面具有非常重要的生物学和临床应用。
附图说明
图1为血型抗原三糖A类似物BSA衍生物合成方法路线图。
具体实施方式
下面结合实施例和实例中的附图,对本发明的技术方案进行清楚、完整的描述,但本发明要求的保护范围并不局限于实施例表述的范围。
实施例1:血型抗原三糖A类似物BSA衍生物的合成
1、血型抗原三糖A类似物与端位连接羧基的叠氮化物的环加成反应
将250mg血型抗原三糖A类似物19慢慢滴入2mL水和甲醇的混合溶液中(水和甲醇的体积比为1:1),超声脱氧15分钟,注射器加入化合物20,加入sodiumascorbate100mg和CuSO450mg,50℃超声反应3小时。蒸干溶剂,C18硅胶反相色谱柱分离,得到240mg 化合物21。
1H-NMR(400MHz,D2O)δ:7.60(s,1H),5.09(d,J=4.0Hz,1H), 4.98(d,J=4.0Hz,1H),4.30(d,J=8.0Hz,1H),4.30-4.20(m,2H), 3.98-3.34(m,19H),2.55(t,J=8.0Hz2H),2.09(t,J=8.0Hz2H), 1.66-1.62(m,4H),1.29(m,2H),0.87(m,4H).
2、血型抗原A类似物交联的蛋白质合成
15mg的牛血清蛋白溶入PBS缓冲溶液中(pH值为5.0,1mL),超声脱氧1分钟,加入5mg步骤(1)所得的化合物三塘21和4mgEDC, 25℃室温下搅拌2小时,水中透析三次,每次12小时,透析后的液体冷冻干燥得到血型抗原A交联的蛋白质22。
实施例2:血型抗原三糖A类似物BSA衍生物的生物学验证
1、western-blot验证血型抗原三糖A类似物BSA衍生物抗原特异性
(1)制胶
配制体积分数为0.08的分离胶、体积分数为0.05的浓缩胶。
(2)抗原样品处理及上样
取一定量的实施例1中制备的血型抗原A类似物的衍生物溶解在样品缓冲液中,分别制备浓度为20μg/mL、10μg/mL、5μg/mL的抗原样品,100℃水浴3至5min,上样。
(3)电泳
接通电源,初始电压为80V,进入分离胶时调至150V,当样品缓冲液中溴酚蓝指示液移至离胶部0.5cm处,关闭电源。
(4)转移
在一浅托盘中加入少量转移缓冲液,先垫上一层多孔性垫片,再垫上3张Whatman3MM滤纸,并将凝胶铺平,盖上NC膜,然后垫上3张Whatman3MM滤纸和一层多孔性垫片,夹好放入转移槽中,连接电源电转2至3小时,电转完毕,取下NC膜,丽春红染色检测蛋白质是否转印完全。
(5)western-blot法检测血型抗原三糖A类似物BSA衍生物特异性抗原
用蒸馏水冲洗被丽春红染色的NC膜,用体积分数为0.05的小牛血清4℃
条件下封闭12h,PBS洗涤,滤纸吸干,切成2mm宽的条带,放入反应槽中。在含有20μg/mL、10μg/mL、5μg/μL的抗原样品的条带上均加入PBS稀释的抗-A单克隆抗体,同时,在另一含有浓度为20μg/mL的抗原样品的条带上加入PBS稀释的抗-B单克隆抗体作对照组,37℃反应1h,洗涤4次,再加入辣根过氧化物酶标记的羊抗人IgG抗体,37℃反应1h,洗涤同上。加入3,3-二氨基联苯胺底物溶液作用10min,2mol/LH2SO4溶液终止反应,观察色带情况。
(6)结论
western-blot实验中抗原电泳后转印至NC膜上经免疫酶染色结果显示,浓度分别为20μg/mL血型抗原、10μg/mL血型抗原、5μg/μL 血型抗原与抗-A单克隆抗体结合显色,而浓度为20μg/mL的抗原样品与抗-B单克隆抗体结合未出现条带。结果证明,血型抗原三糖A类似物BSA衍生物具有抗原特异性。
2、血型抗原A类似物BSA衍生物定量检测抗-A抗体
酶联免疫吸附试验(ELISA)中,血型抗原A类似物BSA衍生物作为抗原可定量检测抗-A抗体。将血型抗原A类似物BSA蛋白稀释至工作浓度,包被ELISA检测板,作为固相抗原以检测抗-A抗体,以抗原浓度与抗体浓度数据拟合标准曲线,以此定量检测抗-A抗体。
Claims (5)
2.根据权利要求1所述的血型抗原三糖A类似物BSA 衍生物的合成方法,其特征在于,所述的步骤(1)的环加成反应的催化剂为CuSO4 /Na ascorbate催化体系。
3.根据权利要求1所述的血型抗原三糖A类似物BSA 衍生物的合成方法,其特征在于,所述的步骤(2)的偶联反应的溶剂为pH值为5.0~6.3的PBS缓冲溶液。
4.根据权利要求1所述的血型抗原三糖A类似物BSA 衍生物的合成方法,其特征在于,所述的步骤(2)的偶联反应中用EDC作为羧基活化剂。
5.权利要求1的血型抗原三糖A类似物BSA 衍生物在制备血液检测试剂中的应用。
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