CN113061128B - 具有聚集诱导发光和宽光谱吸收特性的光敏剂及其制备方法和应用 - Google Patents
具有聚集诱导发光和宽光谱吸收特性的光敏剂及其制备方法和应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于生物化学领域,具体涉及一类具有聚集诱导发光和宽光谱吸收特性的光敏剂的及其制备方法和在杀死癌细胞和细菌中的应用。
背景技术
光动力治疗(photodynamic therapy,PDT)是一种已经被应用于临床的新兴治疗手段。由于非侵入性、治疗区域可以通过光照控制以及不会产生耐药性等优点,光动力学治疗已经被应用于癌症治疗,细菌和真菌感染治疗中。其工作原理是,光敏剂在受到合适波长光的照射下会被激发到单线激发态,单线激发态通过隙间穿越到三线激发态,光敏剂从三线激发态回到基态时,会敏化周围三线态氧分子上,进而产生活性氧。活性氧可以破坏病变组织中的细胞、细菌及真菌等(Adv.Funct.Mater.2018,28,1804632)。光、光敏剂和氧分子是光动力学治疗中的三个要素,而光敏剂在其中起到了至关重要的作用,因此发展高效率光敏剂十分必要。
传统的光敏剂(如含四吡咯结构的光敏剂)由于Π-Π堆积等作用,光敏效率及荧光强度在聚集状态时都会大大减弱(Adv.Mater.2018,30,1801350)。而聚集诱导发光现象(aggregation-induced emission,AIE)的发现为光敏剂的发展提供了新的思路。扭曲的空间构型使得AIE分子在聚集状态时可以减少Π-Π堆积作用。由于分子内运动受限(restriction of intramolecular motion,RIM)原理,AIE分子在聚集状态时可以尽量减少振动和转动带来的能量损失。因此,AIE光敏剂在聚集状态时通常表现为光敏效率和荧光强度的双重增强。另外,生物相容性较好是AIE光敏剂的另一大优点。AIE光敏剂已经成为研究热点(Nanoscale,2019,11,19241),并有望取代传统光敏剂。
发明内容
本发明的目的在于提供一类具有聚集诱导发光和宽光谱吸收特性的光敏剂。该类染料具有聚集诱导发光荧光团及咔唑基团,其主要优点是吸收光谱宽、活性氧产生能力强、黑暗下生物相容性好以及光照下可以有效杀死癌细胞和细菌。
本发明的目的通过下述方案实现:
一种具有聚集诱导发光和宽光谱吸收特性的光敏剂,其结构为式I所示:
式I中,
R1独立选自:C1~C12的烃基,苯基或式II所示基团(其中曲线标记处为取代位,下同;在式II中,n为0~10的整数)中的任意一种;
R2独立选自:吡啶基团、式III所示基团或式IV所示基团的任意一种。
另一方面,本发明还提供了一种上述具有聚集诱导发光和宽光谱吸收特性光敏剂的制备方法,其主要步骤包括:在碱性催化剂(哌啶)的存在下,由式V所示结构的化合物与式VI或式VII所示结构的化合物于有机溶剂(乙腈)中回流反应10-12h,经过Knoevenagel缩合生成式I所示结构的光敏剂。
其中,R1取代基与前文所述相同。
在本发明的一个优选技术方案中:
R1分别独立选自:C1~C12的直链或支链烷基,苯基或式II所示基团(n为0~10的整数)中的任意一种;
R2为吡啶基团、式III所示基团或式IV所示基团的任意一种。
进一步优选的R1为乙基,苯基或式II所示基团(其中n=4)的任意一种;R2为吡啶基团、式III所示基团或式IV所示基团的任意一种。
更进一步优选的R1为苯基。R2为吡啶基团、式III所示基团或式IV所示基团的任意一种。
再更进一步优选的R1为苯基。R2为式III所示基团(其中阴离子为PF6-)
本发明的具有聚集诱导发光和宽光谱吸收特性的光敏剂用于杀死癌细胞或细菌的应用。
附图说明
图1.光敏剂I-6(浓度为10μM)在水中吸收和荧光光谱图,其中,横坐标为波长(nm),纵坐标为归一化的吸光度或荧光强度。
图2.光敏剂I-2和I-3与商业化光敏剂二氢卟吩e6在相同光照条件下产生活性氧能力的比较
图3.光敏剂I-4和I-6与商业化光敏剂二氢卟吩e6在相同光照条件下产生活性氧能力的比较。
图4.光敏剂I-6在黑暗条件或光照条件下对于HeLa细胞的毒性。
图5光敏剂I-6在黑暗条件或光照条件下对于大肠杆菌的毒性。
具体实施方式
下面通过实施例对本发明作进一步的阐述,其目的仅在于更好的理解本发明的内容。因此,所举之例并不限制本发明的保护范围:
实施例1
(1)光敏剂I-1的合成
向的50mL双口烧瓶中依次加入化合物V-1(100mg,0.24mmol),化合物VI(403mg,1.45mmol),乙腈(15mL),哌啶(0.5mL)。在氮气保护下,95℃回流12h。旋转蒸发除去溶剂,柱层析分离(二氯甲烷:甲醇=100:1),得到橙红色固体(光敏剂I-1)52mg,产率23%。
1H NMR(400MHz,DMSO-d6,ppm),δ:11.99(s,1H),8.26(d,4H,J=7.72Hz),7.77-7.70(m,1H),7.70-7.56(m,10H),7.56-7.47(m,6H),7.37(t,4H,J=7.40Hz),7.26-7.10(m,4H),7.05(s,2H),4.37(t,2H,J=7.12Hz),2.15(t,2H,J=7.20Hz),1.76-1.61(m,2H),1.56-1.43(m,2H),1.36-1.25(m,2H).
Mass spectrometry(ESI negative ion mode for[M-H]-):Calcd.forC59H41N6O2S2:929.2732,found:929.2752.
(2)光敏剂I-2的合成
向50mL双口烧瓶中依次加入化合物V-2(200mg,0.61mmol),化合物VI(1020mg,3.68mmol)乙腈(15mL),哌啶(0.75mL)。在氮气保护下,95℃回流12h。旋转蒸发除去溶剂,柱层析分离(二氯甲烷∶甲醇=400∶1),得到红色固体(光敏剂I-2)201mg,产率39%。
1H NMR(400MHz,DMSO-d6,ppm):8.26(d,4H,J=7.72Hz),7.75-7.70(m,1H),7.68(d,2H,J=3.92Hz),7.66-7.55(m,8H),7.55-7.48(m,6H),7.40-7.33(m,4H),7.30-7.00(m,6H),4.42(q,2H,J=6.84Hz),1.31(t,3H,J=7.00Hz).
Mass spectrometry(ESI positive ion mode for[M+H]+):Calcd.forC55H37N6S2:845.2521;found:845.2517.
(3)光敏剂I-3的合成
向50mL双口烧瓶中依次加入化合物V-3(150mg,0.45mmol),化合物VI(958mg,3.45mmol,),乙腈(15mL),哌啶(0.5mL)。在氮气保护下,95℃回流12h。旋转蒸发除去溶剂,柱层析分离(二氯甲烷∶石油醚=4∶1),得到红色固体(光敏剂I-3)156mg,产率39%。
1H NMR(400MHz,DMSO-d6,ppm):8.21(d,4H,J=7.52Hz),7.71-7.64(m,4H),7.64-7.51(m,4H),7.51-7.41(m,12H),7.41-7.37(m,2H),7.37-7.31(m,4H),7.31-7.26(m,2H),7.23(s,2H),5.95(d,2H,J=15.68Hz).
Mass spectrometry(ESI positive ion mode for [M+H]+):Calcd.forC59H37N6S2:893.2521;fbund:893.2512.
(4)光敏剂I-4的合成
向50mL双口烧瓶中依次加入化合物V-3(1215mg,3.25mmol),化合物VI(300mg,1.08mmol),乙腈(15mL),哌啶(0.5mL)。在氮气保护下,95℃回流12h。柱层析分离(二氯甲烷∶石油醚=4∶1),得到红色固体302mg(中间体1),产率44%。
向50mL双口烧瓶中加入中间体1(50mg,0.08mmol),4-吡啶甲醛(171mg,1.60mmo1),乙腈(12mL),哌啶(0.5mL)。在氮气保护下,95℃加热回流12h。旋转蒸发除去溶剂,柱层析分离(二氯甲烷∶甲醇=100∶1),得到红色固体(光敏剂I-4)28mg,产率49%。
1H NMR(400MHz,DMSO-d6,ppm),δ:8.54(d,2H,J=5.96Hz),8.23(d,2H,J=7.72Hz),7.78-7.70(m,1H),7.70-7.57(m,7H),7.54-7.43(m,7H),7.41(d,1H,J=3.88Hz),7.38-7.30(m,3H),7.28(s,1H),7.23(d,2H,J=5.96Hz),7.19(s,1H),6.97(d,1H,J=15.92Hz),6.56(d,1H,J=16.04Hz),5.97(d,1H,J=15.76Hz).
Mass spectrometry(ESI positive ion mode for[M+H]+):Calcd.for C48H31N6S:723.2331;found:723.2330.
(5)光敏剂I-5和I-6的合成
向50mL双口烧瓶中依次加入光敏剂I-4(30mg,0.04mmol),碘甲烷(80mg,0.56mmol),二氯甲烷(6mL)。在室温下搅拌24h。旋转蒸发除去溶剂,柱层析分离(二氯甲烷∶甲醇=15∶1),得到黑色固体(光敏剂I-5)23mg,产率64%。
向50mL双口烧瓶中加入光敏剂I-5(21mg,0.024mmol),丙酮(5mL)。固体溶解后,再向烧瓶中加入饱和的六氟磷酸钾溶液(5mL),常温搅拌过夜。有大量固体析出,抽滤,得到黑绿色固体(光敏剂I-6)14mg,产率66%。
1H NMR(400MHz,DMSO-d6,ppm),δ:8.85(d,2H,J=5.32Hz),8.24(d,2H,J=7.16Hz),8.03(d,2H,J=5.24Hz),7.76-7.59(m,8H),7.57-7.51(m,2H),7.51-7.41(m,6H),7.39-7.21(m,6H),7.01(d,1H,J=15.96Hz),5.97(d,1H,J=15.68Hz),4.24(s,3H).
Mass spectrometry(ESI positive ion mode for[M-PF6]+):Calcd.forC49H33N6S:737.2487;found:737.2485.
实施例2
光敏剂I-6在水中的吸收和荧光光谱
取实施例1中合成的光敏剂I-6溶于分析纯的二甲基亚砜中,制成浓度为1.0×10-3M的储备液(下文称I-6的储备液)。取30μL上述储备液加入到2970μL超纯水中,混合均匀后转移到石英比色皿(10×10mm)中,测试其吸收和荧光光谱。如图1所示,光敏剂I-6在350nm~640nm处呈现宽的吸收峰,且最大吸收波长为512nm。以520nm为激发波长,光敏剂I-6在600nm~800nm处呈现宽的荧光发射峰,且最大发射波长在678nm。
实施例3
光敏剂I-2和I-3在水中产生活性氧的能力
以9,10-蒽二基-二(亚甲基)二丙二酸(ABDA,测试浓度为50μM)为活性氧指示剂测试光敏剂I-2和I-3在水中产生活性氧的能力,同时以市售光敏剂二氢卟吩e6(Ce 6)作为参比对象,光敏剂的测试浓度为10μM。如图2所示,在白光照射后,光敏剂I-2和I-3能够使指示剂在378nm处吸光度较快速的下降,而Ce 6能够使指示剂在378nm处吸光度较缓慢的下降。没有光敏剂的存在下,光照后指示剂的吸光度几乎保持不变。这表明,光敏剂I-2和I-3能够在光照下快速产生活性氧。
实施例4
光敏剂I-4和I-6在水中产生活性氧的能力
以2′,7′-二氯荧光素二乙酸酯(DCFH-DA,测试浓度为40μM)为活性氧荧光指示剂测试光敏剂I-4和I-6在水中产生活性氧的能力,同时以市售光敏剂二氢卟吩e6(Ce 6)作为参比对象,光敏剂的测试浓度为10μM。如图3所示,在白光照射30s后,光敏剂I-4和I-6能够使指示剂的荧光快速增强,而Ce 6能够使指示剂的荧光较缓慢的增强。没有光敏剂的存在下,光照后指示剂的荧光几乎保持不变。这表明,光敏剂1-4和I-6能够在光照下快速产生活性氧。
实施例5
光敏剂I-6对于HeLa细胞的毒性
将HeLa细胞接种到96孔板中(104细胞/孔),分成两组(黑暗组和光照组),在细胞培养箱中培养12h。取I-6的储备液稀释到DMEM培养基中,得到含有不同浓度I-6的培养基(10,5,2.5,1,0μM)。将含有不同浓度I-6的培养基加入到不同孔中。在细胞培养箱中孵育6h,将含有光敏剂的培养基替换为新鲜的培养基。一组细胞置于黑暗中,另一组细胞白光照射15min。两组细胞在培养箱中继续避光培养12h,然后加入5mg/mLMTT(10μL/孔)。4h后,小心移走上层液体,并加入100μLDMSO溶解固体,摇匀后在酶标仪上读数。如图4所示,黑暗组中,光敏剂浓度为10μM时,细胞活性保持在100%左右,表明光敏剂在黑暗条件下具有良好的生物相容性。在光照15min后,10μM光敏剂I-6能使细胞活性降低为8%左右,说明在光照条件下光敏剂I-6能够明显杀死HeLa细胞。
实施例6
光敏剂I-6对于大肠杆菌的毒性
将大肠杆菌培养液稀释到PBS中,平均分成3组。组1:不加光敏剂I-6,在37℃孵育30min后,置于黑暗中。组2:加入光敏剂I-6的储备液(最终光敏剂浓度为10μM),在37℃下孵育30min后,置于黑暗中。组3:加入光敏剂I-6的储备液(最终光敏剂浓度为10μM),在37℃下孵育30min后,白光照射15min。取30μL上述处理过菌液涂布在培养皿中,在37℃下继续避光孵育12h,拍照。结果如图5所示,在10μM光敏剂I-6存在下,黑暗组(组2)的菌落相比于对照组(组1),菌落没有明显减少,而光照组(组3)中菌落明显减少,说明光敏剂I-6在光照下能够明显杀死大肠杆菌。
Claims (4)
2.根据权利要求1所述的具有聚集诱导发光和宽光谱吸收特性的光敏剂,其特征在于,所述R1为苯基。
3.根据权利要求1所述的具有聚集诱导发光和宽光谱吸收特性的光敏剂,其特征在于,所述R2式Ⅲ所示基团;其中阴离子为PF6 -。
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