CN115232089A - 一种乙烯基酚噻嗪类荧光探针及其制备方法和应用 - Google Patents
一种乙烯基酚噻嗪类荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于食品安全分析检测技术领域,涉及一种乙烯基酚噻嗪类荧光探针及其制备方法和应用。
背景技术
食品安全问题直接威胁公众的生命健康,是全球共同面临的重大挑战。鱼和肉类食品在变质过程中受多种腐败细菌酶的作用,蛋白质代谢降解产生尸胺、腐胺、组胺、酪胺、精胺等为代表的生物胺类物质。食品中生物胺的增加是食品新鲜度降低甚至变质的标志,轻则食用风味变差,重则造成食物中毒,危及生命。因此,对生物胺或其单一组分进行高效的检测就成了对肉类食品进行安全评估和质量控制的首要任务,在保障食品安全上具有重大意义。
生物胺类物质可以用经典的仪器分析方法如气质联用、液相色谱、电化学法等精确检测,但这些方法无法让购销双方在现场对食品进行实时、直观高效的检测。通过荧光探针对生物胺类物质进行光学识别,产生肉眼可见的颜色或荧光响应来实现动态检测,因其简单可靠,方便快捷,而且成本低和非破坏性,在鱼肉食品质量检验领域受到了越来越多的青睐。
但生物胺结构多样、成分复杂,目前开发的以生物胺为目标的荧光探针普遍灵敏度较低,而且面临背景干扰的问题。近年来开发的反应型荧光探针虽然在灵敏度和信噪比上有一定程度的提高,但也存在响应速度慢和选择性不高的困境。鱼肉食品质量安全检验领域亟需一种针对生物胺或其单一组分进行特异性、快速、高灵敏检测的荧光探针及实时、现场、可视化的检测方法。
发明内容
本发明的目的在于提供一种乙烯基酚噻嗪类荧光探针及其制备方法和应用,该荧光探针能够针对生物胺或其单一组分进行特异性、快速、高灵敏检测,使用方便、高效。
本发明所采用的技术方案是:
一种乙烯基酚噻嗪类荧光探针,其结构式如下:
式(1)中:R选自C1-18的直链或支链烷基或芳基;G1和G2选自氰基(-CN)、酯基(-COOR1)、(杂)芳基(-Ar)、酰基(-COR1)、氨甲酰基(-CONR2R3)、硝基(-NO2)或磺酸(酯)基(-SO3R1);
其中R1为H、C1-10的直链或支链烷基或(杂)芳基,R2和R3选自H,C1-10的直链或支链烷基、(杂)芳基或酰基。
进一步地,R为C1-8直链烷基,G1和G2选自氰基(-CN)、酯基(-COOR1)、(杂)芳基(-Ar)、酰基(-COR1),其中R1为H、C1-10的直链或支链烷基、(杂)芳基。
一种乙烯基酚噻嗪类荧光探针的制备方法,包括以下步骤:
(1)取酚噻嗪与RI进行取代反应,得到化合物1,其结构式如下:
(2)取步骤(1)制备的化合物1与无水N, N-二甲基甲酰胺和三氯氧磷反应得到3-醛基酚噻嗪,其结构式如下:
(3)取步骤(2)制备的3-醛基酚噻嗪与哌啶、带有吸电子取代基G1和G2的活性亚甲基化合物于醇溶液中,在氮气氛围下加热回流、搅拌反应10 min至1 h,反应液依次经浓缩、过滤、洗涤,即得所述乙烯基酚噻嗪类荧光探针。
进一步地,取代反应过程为:在无水溶剂中、氮气保护条件下,酚噻嗪和NaH作用脱氢质子,然后加入RI,发生取代反应生成N-烷基酚噻嗪。
进一步地,取代反应过程为:取酚噻嗪与碘代芳烃,在金属钯或铜催化下进行反应,氮上的氢被碘代芳烃取代生成N-芳基酚噻嗪。
进一步地,步骤(2)中,N-烷基酚噻嗪与无水N, N-二甲基甲酰胺和三氯氧磷反应的反应过程为:在氮气气氛下,向反应瓶中加入由步骤(1)制备的N-烃基酚噻嗪、以及无水N, N-二甲基甲酰胺和三氯氧磷,加热至50-100 ℃,待反应完全后,倒入冰水中,调节pH至中性析出固体,即得3-醛基酚噻嗪。
进一步地,步骤(3)中,带有吸电子取代基G1和G2的活性亚甲基化合物为丙二腈、氰基乙酸乙酯、腈乙基吡啶中的任意一种。
一种乙烯基酚噻嗪类荧光探针在检测生物胺中的应用。
一种乙烯基酚噻嗪类荧光探针在检测生物胺中的应用,生物胺为酪胺、组胺、尸胺、腐胺、精氨、色胺中的任意一种。
一种生物胺检测用荧光检测试纸条,其特征在于,所述荧光检测试纸条浸渍吸附有上述的乙烯基酚噻嗪类荧光探针。
本发明的有益效果:
1.本发明的乙烯基酚噻嗪类荧光探针在乙烯基碳上连接各种吸电子基团,使共轭双键产生缺电子亲电性质,从而可以与生物胺发生特异性的氮杂迈克加成-消除的串联反应,探针结构的改变产生荧光和颜色的变化,生成相应的具备明显不同光学性质的席夫碱,产生荧光和颜色双重响应,从而实现对尸胺的高灵敏度检测,为鱼肉类食品新鲜度检测提供了一类新型、高效的荧光探针和实时、可视化的检测手段。
2.本发明可通过改变乙烯基结构上连接的吸电子基团对所述荧光探针的生物氨检测性能进行调节,实现对不同生物胺单一组分的选择性检测,并且进一步提高荧光探针的稳定性、对生物胺的灵敏度和快速响应能力。
附图说明
图1为实施例1、2、3合成的三种乙烯基酚噻嗪荧光探针的核磁谱图。
图2为实施例1、2、3合成的三种乙烯基酚噻嗪荧光探针对尸胺的响应灵敏度。
图3为实施例1、2、3合成的三种乙烯基酚噻嗪荧光探针对尸胺的响应速度。
图4为实施例1合成的荧光探针Ⅰ的吸光度与尸胺浓度的线性关系。
图5为实施例1合成的荧光探针Ⅰ的荧光强度与尸胺浓度的线性关系。
图6为实施例1合成的荧光探针Ⅰ对不同浓度尸胺的可视化检测效果图。
图7为实施例1合成的荧光探针Ⅰ对尸胺的选择性;
图8为乙烯基酚噻嗪荧光探针的合成路线图;
图9为实施例所提供生物胺用荧光检测试纸条在不同尸胺浓度中不同光线下的可视化检测效果图;
图10为实施例所提供生物胺用荧光检测试纸条在紫外光照射下对新鲜牛肉放置检测的可视化检测效果图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
本发明提供一种乙烯基酚噻嗪类荧光探针,其结构式如下:
式(1)中:R选自C1-18的直链或支链烷基或芳基;G1和G2选自氰基(-CN)、酯基(-COOR1)、(杂)芳基(-Ar)、酰基(-COR1)、氨甲酰基(-CONR2R3)、硝基(-NO2)或磺酸(酯)基(-SO3R1);
其中R1为H、C1-10的直链或支链烷基或(杂)芳基,R2和R3选自H,C1-10的直链或支链烷基、(杂)芳基或酰基。
优选地,R为C1-8直链烷基,G1和G2选自氰基(-CN)、酯基(-COOR1)、(杂)芳基(-Ar)、酰基(-COR1),其中R1为H、C1-10的直链或支链烷基、(杂)芳基。
本发明还提供一种乙烯基酚噻嗪类荧光探针的制备方法,参考图8所示,包括以下步骤:
(1)取酚噻嗪与RI进行取代反应,得到化合物1,其结构式如下:
(2)取步骤(1)制备的化合物1与无水N, N-二甲基甲酰胺和三氯氧磷反应得到3-醛基酚噻嗪,其结构式如下:
(3)取步骤(2)制备的3-醛基酚噻嗪与哌啶、带有吸电子取代基G1和G2的活性亚甲基化合物于醇溶液中,在氮气氛围下加热回流、搅拌反应10 min至1 h,反应液依次经浓缩、过滤、洗涤,即得所述乙烯基酚噻嗪类荧光探针。
步骤(1)中,取代反应过程为:在无水溶剂中、氮气保护条件下,酚噻嗪和NaH作用脱氢质子,然后加入RI,发生取代反应生成N-烷基酚噻嗪或者取酚噻嗪与碘代芳烃,在金属钯或铜催化下进行反应,氮上的氢被碘代芳烃取代生成N-芳基酚噻嗪。
步骤(2)中,N-烷基酚噻嗪与无水N, N-二甲基甲酰胺和三氯氧磷反应的反应过程为:在氮气气氛下,向反应瓶中加入由步骤(1)制备的N-烃基酚噻嗪、以及无水N, N-二甲基甲酰胺和三氯氧磷,加热至50-100 ℃,待反应完全后,倒入冰水中,调节pH至中性析出固体,即得3-醛基酚噻嗪。
该乙烯基酚噻嗪类荧光探针在检测生物胺中的应用。
其中,生物胺为酪胺、组胺、尸胺、腐胺、精氨、色胺中的任意一种。
实施例1
(1)氮气气氛下,NaH(360 mg, 15 mmol)和酚噻嗪(990 mg, 5 mmol)在25 mL 无水DMF溶剂中室温搅拌1 h,然后缓慢加入碘乙烷(654 mg, 6 mmol),继续搅拌反应1小时,反应完全后将反应液倒入150 mL冰水中,过滤得白色固体产品N-乙基酚噻嗪。
(2)氮气气氛中冰浴条件下,三氯氧磷(0.66 mL, 7 mmol)缓慢滴加入4 mL无水DMF中,搅拌30 min中后,加入N-乙基酚噻嗪(1.14 g, 5 mmol),升温到100℃继续搅拌至完全反应,反应液倒入50 mL冰水中,用饱和碳酸氢钠调pH至中性,二氯甲烷萃取,无水硫酸钠干燥,减压除溶剂后,柱层析(石油醚:乙酸乙酯=10:1)纯化,得N-乙基-3-醛基酚噻嗪。
(3)取丙二腈(1.5 mmol)、N-乙基-3-醛基酚噻嗪(255.3 mg, 1 mmol)、哌啶(0.05mL)加入到10 mL无水乙醇中,加热至85℃搅拌反应30 min,减压旋蒸浓缩,过滤,乙醇洗涤,得到乙烯基酚噻嗪类荧光探针Ⅰ,其结构式如下:
实施例2
(1)氮气气氛下,NaH(360 mg, 15 mmol)和酚噻嗪(990 mg, 5 mmol)在25 mL 无水DMF溶剂中室温搅拌1 h,然后缓慢加入碘乙烷(654 mg, 6 mmol),继续搅拌反应1小时,反应完全后将反应液倒入150 mL冰水中,过滤得白色固体产品N-乙基酚噻嗪。
(2)氮气气氛中冰浴条件下,三氯氧磷(0.66 mL, 7 mmol)缓慢滴加入4 mL无水DMF中,搅拌10 min中后,加入N-乙基酚噻嗪(1.14 g, 5 mmol),升温到50℃继续搅拌至完全反应,反应液倒入50 mL冰水中,用饱和碳酸氢钠调pH至中性,二氯甲烷萃取,无水硫酸钠干燥,减压除溶剂后,柱层析(石油醚:乙酸乙酯=10:1)纯化,得N-乙基-3-醛基酚噻嗪。
(3)取氰基乙酸乙酯(1.5 mmol)、N-乙基-3-醛基酚噻嗪(255.3 mg, 1 mmol)、哌啶(0.05 mL)加入到10 mL无水乙醇中,加热至85℃搅拌反应30 min,减压旋蒸浓缩,过滤,乙醇洗涤,得到乙烯基酚噻嗪类荧光探针Ⅱ,其结构式如下:
实施例3
(1)氮气气氛下,NaH(360 mg, 15 mmol)和酚噻嗪(990 mg, 5 mmol)在25 mL 无水DMF溶剂中室温搅拌1 h,然后缓慢加入碘乙烷(654 mg, 6 mmol),继续搅拌反应1小时,反应完全后将反应液倒入150 mL冰水中,过滤得白色固体产品N-乙基酚噻嗪。
(2)氮气气氛中冰浴条件下,三氯氧磷(0.66 mL, 7 mmol)缓慢滴加入4 mL无水DMF中,搅拌15 min中后,加入N-乙基酚噻嗪(1.14 g, 5 mmol),升温到75℃继续搅拌至完全反应,反应液倒入50 mL冰水中,用饱和碳酸氢钠调pH至中性,二氯甲烷萃取,无水硫酸钠干燥,减压除溶剂后,柱层析(石油醚:乙酸乙酯=10:1)纯化,得N-乙基-3-醛基酚噻嗪。
(3)取氰基乙酸乙酯(1.5 mmol)、N-乙基-3-醛基酚噻嗪(255.3 mg, 1 mmol)、哌啶(0.05 mL)加入到10 mL无水乙醇中,加热至80℃搅拌反应30 min,减压旋蒸浓缩,过滤,乙醇洗涤,得到乙烯基酚噻嗪类荧光探针Ⅲ,其结构式如下:
对实施例1-3所得到的乙烯基酚噻嗪荧光探针Ⅰ、Ⅱ和Ⅲ进行分析,其核磁氢谱和碳谱如图1所示,该乙烯基酚噻嗪类荧光探针在乙烯基碳上连接各种吸电子基团,使共轭双键产生缺电子亲电性质,从而可以与生物胺发生特异性的氮杂迈克加成-消除的串联反应,探针结构的改变产生荧光和颜色的变化。
配制各荧光探针浓度为10 μM的DMSO溶液,向该探针溶液中加入不同浓度的尸胺,测定乙烯基酚噻嗪Ⅰ、Ⅱ和Ⅲ对不同浓度尸胺的荧光响应强度,图2为乙烯基酚噻嗪荧光探针Ⅰ、Ⅱ和Ⅲ检测尸胺的灵敏度,乙烯基酚噻嗪荧光探针Ⅰ、Ⅱ和Ⅲ都对尸胺有一定的荧光响应性能,发出明显的青色荧光,对同等量的尸胺,探针荧光强度随双键上基团的吸电子能力提高而增加。
应用所制备的荧光探针Ⅰ、Ⅱ和Ⅲ验证其对尸胺荧光响应的速度,图3是所述的三种乙烯基酚噻嗪荧光探针对尸胺荧光响应强度随时间的变化曲线,结果表明其对尸胺的荧光响应速度根据其乙烯双键结构上吸电子基团的不同而不同,其中,吸电子最强的二氰乙烯基酚噻嗪荧光探针Ⅰ可在30 S内达到最大荧光强度,显示出实时快速的尸胺检测能力。
应用所制备的荧光探针Ⅰ验证其吸光度与尸胺浓度的线性关系。图4是所述探针溶液在474 nm波长处吸光度随尸胺浓度的变化曲线,结果表明,探针溶液(10 μM)吸光度与尸胺浓度在0~6 μM范围内有良好的线性关系,具备优异的尸胺定量检测能力。
应用实施例1中制备的荧光探针Ⅰ验证其荧光强度与尸胺浓度的线性关系,图5是所述探针溶液的发射光谱在493 nm波长处的荧光强度随尸胺浓度的变化曲线,结果表明,探针溶液(10 μM)荧光强度与尸胺浓度在0~7 μM范围内有良好的线性关系,具备优异的定量检测尸胺的能力。
应用实施例1中制备的荧光探针Ⅰ验证其可视化检测尸胺的效果,图6是所述探针溶液加入不同浓度尸胺后,在自然光和365 nm紫外灯照射下颜色变化的图片,其结果表明,在尸胺浓度在0~7 μM范围内,探针溶液颜色由黄棕色逐渐变为无色,荧光颜色由暗红色逐渐变为亮青色,显示出优异的对尸胺实时可视化检测能力。
应用实施例1中制备的荧光探针Ⅰ验证其对尸胺的选择性,图7是所述探针溶液中加入各种常见干扰物种时溶液的荧光和颜色变化,其结果表明一些常见的离子和生物活性物质对所述探针溶液的荧光和颜色不产生明显的影响,只有在生物胺(尸胺、酪胺和腐胺)存在时才有明显的荧光和颜色变化,特别是对尸胺显示出强烈的荧光增强响应和溶液颜色褪色变化,表明该荧光探针对生物胺,特别是生物胺中的尸胺有选择性的识别检测能力。
在上述生物胺检测中,乙烯基酚噻嗪类荧光探针均以溶液检测的方式进行,其检测过程对配套要求略高,对此,本发明在乙烯基酚噻嗪类荧光探针应用于生物胺检测时,还提供一种生物胺用荧光检测试纸条,该荧光检测试纸条可应用于检测生物胺中,其通过溶液浸渍的方法使本发明所提供的乙烯基酚噻嗪类荧光探针吸附到多孔滤纸上,晾干后即制得荧光检测试纸条,相比溶液法检测更加方便了检测的实现,成本低,易于携带。
如图9所示,通过溶液浸渍的方法使本发明所提供的乙烯基酚噻嗪类荧光探针吸附到多孔滤纸上,晾干后制得荧光检测试纸条,用该检测试纸条检测不同浓度的尸胺,研究了对尸胺的颜色和荧光响应性能。随着所浸染的尸胺浓度逐渐增加,在自然光下,负载试纸条只有较轻微的向浅色方向演变的趋势,但在紫外灯照射下,荧光颜色却呈现出明显变化,随着尸胺浓度增加由红色向青色转变。可以观察到试纸条在1.4 ppm的尸胺浓度下就变为明显的青色,有趣的是,试纸条的初始荧光呈现出与其溶液荧光明显不同的鲜红色,这可能是由滤纸载体表面光的吸收和散射导致的,这也在某种程度上有利于荧光检测的过程。
从市场买来新鲜的牛肉切成小块,与试纸一起密封在表面皿中,在25 ℃条件下放置72小时,中途定时定量取样,加一定量水浸泡取出的牛肉样品,取定量的浸泡液与乙烯基酚噻嗪类荧光探针混匀进行荧光光谱测定。同时,在365 nm紫外光下观察比色皿中溶液以及表面皿中乙烯基酚噻嗪类荧光探针固载试纸的荧光颜色变化。
空白乙烯基酚噻嗪类荧光探针溶液在498 nm处几乎无荧光发射,新鲜牛肉样品的提取液却能使乙烯基酚噻嗪类荧光探针产生较高的498 nm荧光峰,而且荧光强度随着牛肉放置时间的延长持续上升,到48小时上升速度大幅增加,表明新鲜牛肉本身就含有储藏运输过程中产生的或自身代谢产生的内源性尸胺,而且随放置时间延长,逐渐变质腐败,产生更多的尸胺,当在25℃放置36小时后,变质速度加快。从样品溶液的荧光颜色变化也可以清晰的观察得到同样的结论,由于乙烯基酚噻嗪类荧光探针溶液对尸胺的响应极为灵敏,新鲜牛肉中尸胺的含量就已经超过了其荧光响应阀值,这反而增加了通过观察溶液荧光颜色的变化来判断牛肉是否变质的复杂性。
而上述复杂性可以由乙烯基酚噻嗪类荧光探针负载的试纸很好的解决,从图10可以看出,由于环境中的尸胺浓度相对牛肉本身要低得多,与新鲜牛肉放置在一起的检测试纸在紫外光照射下无法响应,显示为其本身固有的暗红色荧光,12 小时后由于牛肉变质,向环境中释放的尸胺增加,超过乙烯基酚噻嗪类荧光探针负载试纸的检测限,从而能够做出响应并发出明亮的蓝绿色荧光,虽然继续延长放置时间其荧光颜色变化不明显,但从0-12小时期间荧光颜色的明显变化,可以很清晰的指示牛肉从新鲜到变质的过程,表明乙烯基酚噻嗪类荧光探针负载型试纸可作为一种方便高效的便携式荧光传感器,可服务于肉类食品安全和质量检测领域,对尸胺进行快速可视化的原位实时检测,从而监控肉类食品的新鲜度或变质过程。
需要说明的是,上述实施例仅用来说明本发明,但本发明并不局限于上述实施例,凡是依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰,均落入本发明的保护范围内。
Claims (10)
2.如权利要求1所述的一种乙烯基酚噻嗪类荧光探针,其特征在于,R为C1-8直链烷基,G1和G2选自氰基(-CN)、酯基(-COOR1)、(杂)芳基(-Ar)、酰基(-COR1),其中R1为H、C1-10的直链或支链烷基、(杂)芳基。
4.如权利要求3所述一种乙烯基酚噻嗪类荧光探针的制备方法,其特征在于,步骤(1)中,取代反应过程为:在无水溶剂中、氮气保护条件下,酚噻嗪和NaH作用脱氢质子,然后加入RI,发生取代反应生成N-烷基酚噻嗪。
5.如权利要求3所述一种乙烯基酚噻嗪类荧光探针的制备方法,其特征在于,步骤(1)中,取代反应过程为:取酚噻嗪与碘代芳烃,在金属钯或铜催化下进行反应,氮上的氢被碘代芳烃取代生成N-芳基酚噻嗪。
6.如权利要求3所述一种乙烯基酚噻嗪类荧光探针的制备方法,其特征在于,步骤(2)中,N-烷基酚噻嗪与无水N, N-二甲基甲酰胺和三氯氧磷反应的反应过程为:在氮气气氛下,向反应瓶中加入由步骤(1)制备的N-烃基酚噻嗪、以及无水N, N-二甲基甲酰胺和三氯氧磷,加热至50-100 ℃,待反应完全后,倒入冰水中,调节pH至中性析出固体,即得3-醛基酚噻嗪。
7.如权利要求3所述一种乙烯基酚噻嗪类荧光探针的制备方法,其特征在于,步骤(3)中,带有吸电子取代基G1和G2的活性亚甲基化合物为丙二腈、氰基乙酸乙酯、腈乙基吡啶中的任意一种。
8.如权利要求1或2所述一种乙烯基酚噻嗪类荧光探针在检测生物胺中的应用。
9.如权利要求8所述一种乙烯基酚噻嗪类荧光探针在检测生物胺中的应用,其特征在于,所述生物胺为酪胺、组胺、尸胺、腐胺、精氨、色胺中的任意一种。
10.一种生物胺检测用荧光检测试纸条,其特征在于,所述荧光检测试纸条浸渍吸附有权利要求1或2所述的乙烯基酚噻嗪类荧光探针。
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