CN115594637A - 一种脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针及其制备方法和应用 - Google Patents
一种脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针及其制备方法和应用 Download PDFInfo
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- CN115594637A CN115594637A CN202211188107.4A CN202211188107A CN115594637A CN 115594637 A CN115594637 A CN 115594637A CN 202211188107 A CN202211188107 A CN 202211188107A CN 115594637 A CN115594637 A CN 115594637A
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- bromo
- methyl ester
- acid methyl
- dehydroabietic acid
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Abstract
本发明公开了一种脱氢枞酸基5‑溴‑2‑羟基苯基苯并咪唑功能型荧光探针及其制备方法和应用,包括,脱氢枞酸经过酰氯化、甲酯化、溴代和双硝化反应,制得12‑溴‑13,14‑二硝基脱氢枞酸甲酯;12‑溴‑13,14‑二硝基脱氢枞酸甲酯经过Fe/HCl还原,制得12‑溴‑13,14‑二氨基脱异丙基脱氢枞酸甲酯;12‑溴‑13,14‑二氨基脱异丙基脱氢枞酸甲酯与5‑溴水杨醛反应制得所述荧光探针。本发明制备的甲基‑11‑溴‑2‑(5‑溴‑2‑羟基苯基)‑6,9a‑二甲基‑4,5,5a,6,7,8,9,9a‑八氢‑3H‑菲啰[1,2‑d]咪唑‑6‑甲酯(CPL),能选择性的与HPO4 2‑络合,荧光由青色变为蓝紫色,该化合物可作为荧光探针检测HPO4 2‑;并且在生物成像中有效鉴别HPO4 2‑。
Description
技术领域
本发明属于设计精细有机合成领域,具体涉及到一种脱氢枞酸基5-溴-2- 羟基苯基苯并咪唑功能型荧光探针及其制备方法和应用。
背景技术
磷酸氢根在人体中参与重要的生物过程,如细胞信号传导,能量交换, DNA合成,跨膜转运等,过量的磷酸盐会导致一系列疾病的发生,如高磷血症和心血管疾病,磷酸氢根离子是体内重要的体液酸碱平衡缓冲,维持着人体的酸碱平衡。当体液过酸时,磷酸氢根就会与酸结合生成磷酸二氢根,吸收氢离子。反之,体内酸不足时磷酸二氢根分解成磷酸氢根,磷酸氢根分解成磷酸根离子,产生氢离子,是体液重新达到平衡。
磷酸氢根对蛋白质、胶阮球蛋白具有增强作用,因而可提高肉制品的水合性和持水性,提高水的浸透性,促进食品的软化和改善食品的质量,保持食品的风味。同时磷酸盐在乳制品中能防止牛奶加热时的凝聚,防止酪蛋白与脂肪水分的分离。通常还作焙烤制品膨松剂的膨松酸,和碳酸氢盐反应为焙烤过程提供所需的二氧化碳气体。
然而目前检测磷酸氢根的方法并不多,同时荧光探针检测磷酸氢根的方法也少有报道。
发明内容
本部分的目的在于概述本发明的实施例的一些方面以及简要介绍一些较佳实施例。在本部分以及本申请的说明书摘要和发明名称中可能会做些简化或省略以避免使本部分、说明书摘要和发明名称的目的模糊,而这种简化或省略不能用于限制本发明的范围。
鉴于上述和/或现有技术中存在的问题,提出了本发明。
因此,本发明的目的是,克服现有技术中的不足,提供一种脱氢枞酸基5- 溴-2-羟基苯基苯并咪唑功能型荧光探针。
为解决上述技术问题,本发明提供了如下技术方案:一种脱氢枞酸基5- 溴-2-羟基苯基苯并咪唑功能型荧光探针,该化合物名称为甲基-11-溴-2-(5-溴 -2-羟基苯基)-6,9a-二甲基-4,5,5a,6,7,8,9,9a-八氢-3H-菲啰[1,2-d]咪唑-6-甲酯,结构式为:
本发明的再一个目的是,克服现有技术中的不足,提供一种脱氢枞酸基5- 溴-2-羟基苯基苯并咪唑功能型荧光探针的制备方法。
为解决上述技术问题,本发明提供了如下技术方案:一种脱氢枞酸基5- 溴-2-羟基苯基苯并咪唑功能型荧光探针的制备方法,包括,
脱氢枞酸经过酰氯化、甲酯化、溴代和双硝化反应,制得12-溴-13,14- 二硝基脱氢枞酸甲酯;
12-溴-13,14-二硝基脱氢枞酸甲酯经过Fe/HCl还原,制得12-溴-13,14- 二氨基脱异丙基脱氢枞酸甲酯;
12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯与5-溴水杨醛反应制得所述荧光探针。
作为本发明所述制备方法的一种优选方案,其中:所述12-溴-13,14-二硝基脱氢枞酸甲酯,其制备方法,包括,
向脱氢枞酸甲苯溶液中加入二氯亚砜进行反应,反应结束后真空旋干,加入甲醇进行甲酯化反应,反应结束后旋干,加入乙醇溶解结晶,得到脱氢枞酸甲酯;其中,所述脱氢枞酸甲苯溶液的浓度为0.4~0.6g/mL,脱氢枞酸与二氯亚砜的用量比为1g:0.2~0.3mL,脱氢枞酸与甲醇的用量比为1g:1~3mL;所述脱氢枞酸与二氯亚砜的反应温度为75~80℃,反应时间为2~4h;所述甲酯化反应温度为75~80℃,反应时间为2~4h;
向脱氢枞酸甲酯的乙腈溶液中加入N-溴代丁二酰亚胺NBS,避光常温反应,反应结束后旋蒸,二氯甲烷洗涤两次,甲醇溶解结晶,得到12-溴代脱氢枞酸甲酯;其中,所述脱氢枞酸甲酯乙腈溶液的浓度为0.15~0.20g/mL,脱氢枞酸甲酯与NBS的用量比1:1.2~1:1.5,反应时间为20~24h;
在冰浴条件下,将12-溴脱氢枞酸甲酯加入到发烟硝酸与浓硫酸充分混合的混酸中,进行搅拌,反应结束后直接倒入冰水中静置,减压抽滤,水洗多次,用石油醚:乙酸乙酯的体积比500:1-200:1过柱提纯,制得纯12-溴-13,14-二硝基脱氢枞酸甲酯;其中,12-溴脱氢枞酸甲酯与发烟硝酸用量比为1g:6~7ml,12- 溴脱氢枞酸甲酯与浓硫酸的用量比为1~3g:1ml,所述硝化反应在冰浴条件下反应0.5~1.5h。
作为本发明所述制备方法的一种优选方案,其中:所述12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯,其制备方法包括,
将12-溴-13,14-二硝基脱异丙基脱氢枞酸甲酯溶于HFIP和蒸馏水中,与铁粉、浓盐酸反应,搅拌回流,反应结束,过滤铁粉,用饱和碳酸氢钠中和至中性,用石油醚:乙酸乙酯体积比为28:1,过柱提纯,制得纯12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯;
其中,12-溴-13,14-二硝基脱氢枞酸甲酯与蒸馏水的用量比0.22g:1ml,12- 溴-13,14-二硝基脱氢枞酸甲酯与铁粉用量比0.22g:0.5g,12-溴-13,14-二硝基脱氢枞酸甲酯与浓盐酸的用量比0.22g:800μl,12-溴-13,14-二硝基脱氢枞酸甲酯与 HFIP用量比1g:4~5ml,反应时间为4.5h。
作为本发明所述制备方法的一种优选方案,其中:所述12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯与5-溴水杨醛反应,其中,以DMA作为有机溶剂,亚硫酸氢钠作催化剂,5-溴水杨醛与纯12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯反应用量摩尔比为1:1,反应温度为110℃,反应时间为10~12h;反应结束后,在室温下静置析出固体,制得纯的探针。
本发明的另一个目的是,克服现有技术中的不足,提供一种脱氢枞酸基5- 溴-2-羟基苯基苯并咪唑功能型荧光探针在检测磷酸氢根中的应用,其中:荧光探针在磷酸氢根作用下,荧光由青色变为蓝紫色,检测限为27.5nM,荧光探针对HPO4 2-离子的检测不受其他共存离子的干扰。
本发明的再一个目的是提供所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针在细胞成像和斑马鱼成像中的应用。
本发明的另一个目的是提供所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针在检测奶酪、冻虾、巴沙鱼、牛奶、面包中的应用。
本发明有益效果:
本发明利用天然可再生资源歧化松香中提取的脱氢枞酸为原料制备的甲基-11-溴-2-(5-溴-2-羟基苯基)-6,9a-二甲基-4,5,5a,6,7,8,9,9a-八氢-3H-菲啰[1,2-d] 咪唑-6-甲酯(CPL),能选择性的与HPO4 2-络合,荧光由青色变为蓝紫色,该化合物可作为荧光探针检测HPO4 2-;并且在生物成像中有效鉴别HPO4 2-。
附图说明
为了更清楚地说明本发明实施例的技术方案,下面将对实施例描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动性的前提下,还可以根据这些附图获得其它的附图。其中:
图1为本发明实施例中合成甲基-11-溴-2-(5-溴-2-羟基苯基)-6,9a-二甲基 -4,5,5a,6,7,8,9,9a-八氢-3H-菲啰[1,2-d]咪唑-6-甲酯的工艺图。
图2为本发明实施例中荧光探针CPL溶液中加入HPO4 2-的荧光吸收光谱图。
图3为本发明实施例中荧光探针CPL与不同离子作用的荧光吸收光谱图。
图4为本发明实施例中探针以及加入不同检测离子在洋葱表皮细胞内荧光成像图。
图5为本发明实施例中加入不同检测离子在斑马鱼内荧光成像图。
具体实施方式
为使本发明的上述目的、特征和优点能够更加明显易懂,下面结合说明书实施例对本发明的具体实施方式做详细的说明。
在下面的描述中阐述了很多具体细节以便于充分理解本发明,但是本发明还可以采用其他不同于在此描述的其它方式来实施,本领域技术人员可以在不违背本发明内涵的情况下做类似推广,因此本发明不受下面公开的具体实施例的限制。
其次,此处所称的“一个实施例”或“实施例”是指可包含于本发明至少一个实现方式中的特定特征、结构或特性。在本说明书中不同地方出现的“在一个实施例中”并非均指同一个实施例,也不是单独的或选择性的与其他实施例互相排斥的实施例。
本发明中歧化松香,购于广东封开华林有限公司(脱氢枞酸含量为 59.93%);层析硅胶(300-400目),购于青岛海洋化工厂,化学纯;乙醇胺,购于安徽泽生科技有限公司,分析纯;铁粉,购于天津市风船化学试剂科技有限公司,分析纯;邻苯二胺,购于成都科龙化工试剂厂,分析纯;5-溴水杨醛,购于萨恩化学技术有限公司。
实施例1
本实施例提供一种脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针的制备方法,具体步骤如下:
(1)12-溴-13-硝基脱氢枞酸甲酯的制备:脱氢枞酸经过甲酯化、溴代和硝化反应制得,参见图1,具体过程如下:
称取30g脱氢枞酸溶于60mL的甲苯中,加入11mL的二氯亚砜在78-80℃中反应3h,真空旋干,加入60mL甲醇,在78-80℃下反应3h,旋干,加入30mL 乙醇溶解结晶,得到脱氢枞酸甲酯;
准确称取5g脱氢枞酸甲酯,溶于30mL乙腈中,加入4gN-溴代丁二酰亚胺,避光常温反应24h,旋蒸,二氯甲烷洗涤两次,100mL甲醇溶解结晶,得到12-溴代脱氢枞酸甲酯;
12-溴-13,14-二硝基脱氢枞酸甲酯:
准确称取3g 12-溴代脱氢枞酸甲酯溶于19mL发烟硝酸和1.5mL的浓硫酸中,在冰浴条件下反应1h,反应结束后倒入冰水中,用二氯甲烷萃取三次,水洗三次,饱和碳酸氢钠水溶液洗一次,饱和食盐水洗一次,无水硫酸钠干燥除水,用20mL乙醇重结晶,得到淡黄色的12-溴-13,14-二硝基脱氢枞酸甲酯。
(2)12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯:
准确称取0.44g 12-溴-13,14-二硝基脱氢枞酸甲酯溶于10mL乙醇中,加入铁粉0.56g,20mL盐酸溶液(2mol/L),45℃下搅拌反应1h,反应结束后用乙酸乙酯萃取三次,水洗三次,饱和碳酸氢钠水溶液洗一次,饱和食盐水洗一次,无水硫酸钠干燥除水,旋干得到粗的油状的12-溴-13,14-二氨基脱氢枞酸甲酯。
(3)探针CPL的制备,12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯与3-(1H- 苯并[d]咪唑-2-基)-2-羟基-5-甲基苯甲醛反应制得,具体过程如下:
准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10ml DMA中,加入120mg亚硫酸氢钠,温度为110℃,回流搅拌过夜,反应结束后置于室温下重结晶得到纯的探针CPL。
产物的表征数据为:M.p.159.2-160.3℃;1H NMR(600MHz,DMSO-d6)δ1.23 (d,J=13.0Hz,6H),1.38(td,J=12.8,3.4Hz,1H),1.43–1.51(m,1H),1.60(d,J= 12.8Hz,1H),1.68(td,J=14.1,13.2,3.4Hz,2H),1.76(ddd,J=18.1,9.5,3.6Hz,1H), 1.90(d,J=15.1Hz,1H),2.15(d,J=12.3Hz,1H),2.36–2.42(m,1H),2.89(dt,J= 18.3,9.8Hz,1H),3.11(dd,J=17.3,6.4Hz,1H),3.64(s,3H),7.01(d,J=8.7Hz,1H), 7.41(s,1H),7.52(dd,J=8.9,2.4Hz,1H),8.45(m,1H),13.02(s,1H),13.26(s,1H). .ESI-MS:m/z calcd forC25H26Br2N2O3[M+H]+560.0310,found 561.0387。
实施例2
脱氢枞酸基席夫碱衍生物的制备方法的优化:
试验1:准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10ml DMA中,加入120mg亚硫酸氢钠,温度为110℃,回流搅拌12h,反应结束后置于室温下重结晶得到纯的探针CPL,产率为95%
试验2:准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10ml DMA中,加入120mg对甲苯磺酸,温度为110℃,回流搅拌12h,反应结束后置于室温下重结晶得到纯的探针CPL,产率为63%。
试验3:准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10mlDMA中,温度为78℃,回流搅拌12h,反应结束后置于室温下重结晶得到纯的探针CPL,产率为23%。
试验4:准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10mlDMA中,温度为110℃,回流搅拌5h,反应结束后置于室温下重结晶得到纯的探针CPL,产率为53%。
试验5:准确称量0.44g 12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯和0.23g 5-溴水杨醛,超声于10ml乙醇中,温度为110℃,回流搅拌12h,反应结束后置于室温下重结晶得到纯的探针CPL,产率为62%。
表1不同条件下探针CPL的产率
注:/表示无催化剂。
从表1可以看出,试验1的条件相对于其他反应条件较高的反应得率,因此采用此优选条件进行反应。
实施例3
将探针CPL溶于DMSO中,配制成1×10-3M的溶液,取100μL原液加入 10ml DMSO水溶液(DMSO:水体积比为2:8)中,配制成10×10-6M的溶液,每次加入5μL HPO4 2-,测得不同浓度离子对探针CPL吸收光谱图。
如图2所示,加入HPO4 2-后,随着HPO4 2-浓度的增加,480nm处青色荧光逐渐减弱逐渐猝灭,433nm处荧光逐渐增强,可以看出,在0~90μM的HPO4 2-浓度范围内,化合物CPL的荧光强度与离子的浓度具有很好的线性相关性,线性回归方程y=0.03071x+0.01655(R2=0.99639),计算得HPO4 2-的检测限为 27.5nM。
上述结果说明CPL能HPO4 2-发生络合。
实施例4
将探针CPL溶于DMSO中,配制成1×10-3M的溶液,取100μL原液加入 10ml乙醇水溶液(DMSO:水2:8)中,配制成1×10-5M的溶液,每次加入100 μL(1×10-3M)HPO4 2-以及等摩尔量的其他离子及分析物,如P2O7 4-,PO4 3-,P3O10 5-, SO4 2-,CrO7 2-,CO3 2-,NO4 -,ClO-,SO4 2-,HSO3 -,H2PO4 -,NO2 -,SO3 -,NH4 +,Al3+,Zn2+, Cu2+,Mg2+,Na+,Cd2+,H2O2,N2H4,Cysteine。
如图3所示,在365nm紫外灯下观察,加入HPO4 2-后,随着HPO4 2-浓度的增加,480nm处青色荧光逐渐减弱逐渐猝灭,433nm处蓝紫色荧光逐渐增强,说明化合物与HPO4 2-络合,而与其他离子不发生反应。说明该化合物可以作为一种有效识HPO4 2-离子的荧光探针。
实施例5
探针的生物成像应用:
为探究CPL对细胞HPO4 2-传感适用性,将从菜市场买来的新鲜洋葱取其内芯白色部分,撕下表皮,将表皮放入装有水的六孔板中,然后分别向六孔板加入探针(10μM),浸泡半小时后分别加入0μM、15μM、30μM的HPO4 2-,然后浸泡过夜。次日,用清水洗3次除去多余离子。随后在激光共聚焦显微镜下成像。
如图4所示,可以看出,CPL进入细胞显示出青色荧光,表明探针可以穿透细胞膜,并有效进行细胞成像;随着HPO4 2-浓度的增加,青色荧光逐渐消失,蓝紫色荧光逐渐增强,说明离子可以扩散到细胞,并对探针发生作用,说明该探针成功用于细胞成像,具有检测HPO4 2-的作用。
实施例6
将斑马鱼卵倒入烧杯中,加入营养液,将烧杯置于装有水的恒温水浴锅中,温度调至26℃,放置1-3天进行孵化,待斑马鱼孵化,在六孔板中放置幼鱼,分别加入探针(10μM),其中一个孔不加离子作对照,在另外三孔中分别加入0μM、15μM、30μM的HPO4 2-,继续恒温培养3h。
随后在激光共聚焦显微镜下成像,如图5所示,可以看出,探针CPL在鱼体内显示出青色荧光,表明探针可以进入鱼体内,并有效进行成像,随着HPO4 2-浓度的增加,青色荧光逐渐消失,蓝紫色荧光逐渐增强,说明离子可以扩散到鱼体内,并对探针发生作用,说明该探针成功用于生物成像,具有检测HPO4 2-的作用。
实施例7
从超市购买的奶酪、冻虾、巴沙鱼、牛奶、面包,取适量食物样品,放入研钵中,倒入液氮研磨成粉末状,其中奶酪称取2.3193g,冻虾称取2.9531g,巴沙鱼2.4561g,面包1.5024g,溶解于装有200ml去离子水的圆底烧瓶中,搅拌24小时,离心机离心取上层清液,具塞试管中配制8ml水与2mlDMSO的体系,加入100μL探针和100μL食品清液,在荧光分光光度计测量其荧光强度,如表1所示,计算出食品中HPO4 2-的含量。
表1
应说明的是,以上实施例仅用以说明本发明的技术方案而非限制,尽管参照较佳实施例对本发明进行了详细说明,本领域的普通技术人员应当理解,可以对本发明的技术方案进行修改或者等同替换,而不脱离本发明技术方案的精神和范围,其均应涵盖在本发明的权利要求范围当中。
Claims (10)
2.权利要求1所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针的制备方法,其特征在于:包括,
脱氢枞酸经过酰氯化、甲酯化、溴代和双硝化反应,制得12-溴-13,14-二硝基脱氢枞酸甲酯;
12-溴-13,14-二硝基脱氢枞酸甲酯经过Fe/HCl还原,制得12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯;
12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯与5-溴水杨醛反应制得所述荧光探针。
3.如权利要求2所述的制备方法,其特征在于:所述12-溴-13,14-二硝基脱氢枞酸甲酯,其制备方法,包括,
向脱氢枞酸甲苯溶液中加入二氯亚砜进行反应,反应结束后真空旋干,加入甲醇进行甲酯化反应,反应结束后旋干,加入乙醇溶解结晶,得到脱氢枞酸甲酯;其中,所述脱氢枞酸甲苯溶液的浓度为0.4~0.6g/mL,脱氢枞酸与二氯亚砜的用量比为1g:0.2~0.3mL,脱氢枞酸与甲醇的用量比为1g:1~3mL;所述脱氢枞酸与二氯亚砜的反应温度为75~80℃,反应时间为2~4h;所述甲酯化反应温度为75~80℃,反应时间为2~4h;
向脱氢枞酸甲酯的乙腈溶液中加入N-溴代丁二酰亚胺NBS,避光常温反应,反应结束后旋蒸,二氯甲烷洗涤两次,甲醇溶解结晶,得到12-溴代脱氢枞酸甲酯;其中,所述脱氢枞酸甲酯乙腈溶液的浓度为0.15~0.20g/mL,脱氢枞酸甲酯与NBS的用量比1:1.2~1:1.5,反应时间为20~24h;
在冰浴条件下,将12-溴脱氢枞酸甲酯加入到发烟硝酸与浓硫酸充分混合的混酸中,进行搅拌,反应结束后直接倒入冰水中静置,减压抽滤,水洗多次,用石油醚:乙酸乙酯的体积比500:1-200:1过柱提纯,制得纯12-溴-13,14-二硝基脱氢枞酸甲酯;其中,12-溴脱氢枞酸甲酯与发烟硝酸用量比为1g:6~7ml,12-溴脱氢枞酸甲酯与浓硫酸的用量比为1~3g:1ml,所述硝化反应在冰浴条件下反应0.5~1.5h。
4.如权利要求2所述的制备方法,其特征在于:所述12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯,其制备方法包括,
将12-溴-13,14-二硝基脱异丙基脱氢枞酸甲酯溶于HFIP和蒸馏水中,与铁粉、浓盐酸反应,搅拌回流,反应结束,过滤铁粉,用饱和碳酸氢钠中和至中性,用石油醚:乙酸乙酯体积比为28:1,过柱提纯,制得纯12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯;
其中,12-溴-13,14-二硝基脱氢枞酸甲酯与蒸馏水的用量比0.22g:1ml,12-溴-13,14-二硝基脱氢枞酸甲酯与铁粉用量比0.22g:0.5g,12-溴-13,14-二硝基脱氢枞酸甲酯与浓盐酸的用量比0.22g:800μl,12-溴-13,14-二硝基脱氢枞酸甲酯与HFIP用量比1g:4~5ml,反应时间为4.5h。
5.如权利要求2所述的制备方法,其特征在于:所述12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯与5-溴水杨醛反应,其中,以DMA作为有机溶剂,亚硫酸氢钠作催化剂,5-溴水杨醛与纯12-溴-13,14-二氨基脱异丙基脱氢枞酸甲酯反应用量摩尔比为1:1,反应温度为110℃,反应时间为10~12h;反应结束后,在室温下静置析出固体,制得纯的探针。
6.权利要求1所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针在检测磷酸氢根中的应用。
7.如权利要求6所述的应用,其特征在于:荧光探针在磷酸氢根作用下,荧光由青色变为蓝紫色,检测限为27.5nM。
8.如权利要求6所述的应用,其特征在于:荧光探针对HPO4 2-离子的检测不受其他共存离子的干扰。
9.权利要求1所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针在细胞成像和斑马鱼成像中的应用。
10.权利要求1所述脱氢枞酸基5-溴-2-羟基苯基苯并咪唑功能型荧光探针在检测奶酪、冻虾、巴沙鱼、面包中的应用。
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