CN113234075B - 一种水溶性苝酰亚胺类光动力抗菌电解质和其在光动力杀菌领域的应用 - Google Patents
一种水溶性苝酰亚胺类光动力抗菌电解质和其在光动力杀菌领域的应用 Download PDFInfo
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Abstract
本发明公开了一种光动力抗菌的苝酰亚胺类电解质和其在光动力抗菌领域的用途。该电解质主体结构为苝酰亚胺,侧链结构含有季铵盐官能团,具有良好的水溶性。当电解质与细菌共同孵育,电解质通过静电作用富集于细菌之上。由于苝酰亚胺主体结构在一定波长范围内能与氧等发生能量转移,产生具有抗菌效果的活性氧,加上季铵盐基团所具有的杀菌特性,因此在一定波长和光强下,光动力抗菌电解质将通过活性氧和季铵盐的杀菌效果,杀死细菌。该电解质在较低浓度时就能达到99%以上的杀菌效果,应用前景广阔。
Description
技术领域
本发明涉及光动力抗菌疗法在医学卫生领域及其他工业领域的应用,具体涉及一种光动力抗菌电解质的制备及其用途,更确切的说,本发明涉及一种由主体结构为苝酰亚胺,含有季铵盐官能团侧链结构的光动力抗菌电解质制备,以及其用于对目标处理区域进行光动力杀菌时,对革兰氏阳性菌、革兰氏阴性菌、真菌及寄生性原生生物等致病性微生物具有抑制和杀灭作用。
背景技术
近年来由于抗生素的滥用,许多致病微生物产生耐药性,对人类的卫生健康有极大危害,因此人们越来越关注光动力抗菌疗法的应用,光动力抗菌疗法(AntibacterialPhotodynamic Therapy,APDT)也被证实在细菌等病原体感染临床治疗有较高疗效。
相对于传统药物疗法,光动力抗菌疗法有三个优势:(1)副作用小、安全性高、可重复治疗,光敏剂可选择性结合病原体,对哺乳动物细胞不产生毒副作用,靶向性强;(2)对病原体的灭活过程不会产生耐药性,避免产生耐药性强的超级细菌;(3)具有广泛抗菌谱,对各种微生物及其耐药菌株都有杀灭效果。
光动力抗菌疗法基本原理是:光敏剂通过静电作用在致病微生物细胞的细胞膜附近富集,接着以所述光强和合适波长范围对目标处理区实施日光灯光照射,光敏剂从基态激发到三线态,随后通过电子或氢原子转移生成羟基自由基、过氧化氢及超氧离子等活泼物质(I型反应),或者三线态的光敏剂与三线态氧发生能量传递,生成单线态氧(II型反应)。这些自由基、单线态氧等成分统称活性氧,通过脂质过氧化、细胞膜和细胞壁损伤和细胞内组件的破坏,导致细胞死亡。
苝酰亚胺类材料近年来由于大的π-π共轭电子体系,表现出优异的光电性能,在可见光范围内有强的吸收,目前对其研究已经涉及太阳能电池、电致发光、生物荧光探针和生物治疗等。
光动力抗菌电解质结构包含苝酰亚胺主体以及季铵盐侧链,季铵盐为阳离子型抗菌剂,可以改变致病性微生物细胞膜的通透性,使微生物胞体物质外渗,代谢受阻而死,季铵盐侧链也可以使电解质具有较好的水溶性,以便运用在不同的场景和领域中。
发明内容
本发明目的是提供一种用于光动力抗菌的苝酰亚胺类光敏电解质,该材料具有水溶性,结构具有可设计性,有广谱抗菌能力,能应用于生物医学领域。
为了实现上述目的,本发明第一方面提供了一种苝酰亚胺类光动力抗菌电解质,该电解质具有如下所示的结构,
其中,A1、A2为相同或不相同的侧链;R1、R2、R3、R4为相同或不相同的共轭结构。
所述的R1、R2、R3、R4具有如下结构的一种:
X为Cl,HSO4,HCO3,CFCO3,H2PO4。
M为Cu、Fe、Zn、Ni、Co等金属原子。
所述的A1、A2相同或不同的分别为以下结构的一种:
其中n为1-15的整数。
本发明第二方面提供了本发明第一方面所述光动力抗菌电解质用于对目标处理区域进行光动力杀菌治疗的方法,该方法对目标处理区域内的革兰氏阳性菌、革兰氏阴性菌、真菌及寄生性原生生物等致病微生物有抑制和杀灭作用。
本发明的光动力抗菌电解质结构主体为苝酰亚胺,结构中带有季铵盐官能团侧链。光动力抗菌电解质最大吸收波长范围在300nm-2000nm内,受到光的辐照度为0.01mw/cm2-1000mw/cm2内,使用浓度不大于1mg/ml。光敏剂浓度可以根据实际需要进行调整。
光动力抗菌电解质具有附图1中式I的一种结构单元。
药学上可接受的载体是指粘度调节剂、pH值调节剂、稳定剂、赋形剂等其它药学上可接受的载体,药物可接受的载体优选列于美国药典、日本药局方、中国药典的药用辅料。药学上可接受的载体应与光敏剂、季铵盐类具有良好的相容性
本发明提供了光动力抗菌电解质的用途:i以适当的方式向目标处理区域应用电解质;ii以所述电解质最大吸收的波长向目标处理区域应用光,从而杀灭目标处理区域内的革兰氏阳性菌、革兰氏阴性菌、真菌及寄生性原生生物等致病微生物。
目标处理区域是纱布、钱包、行李箱、手机壳、桌布、人类皮肤粘膜表面、伤口等。目标处理区域应存在革兰氏阳性菌、革兰氏阴性菌、真菌及寄生性原生生物等致病微生物引起的局部污染。可以根据目标处理区域存在的局部污染的性质及程度实施多次光动力杀菌治疗。
与现有技术相比,本发明的优势在于:
与传统抗菌材料不同,本产品具有水溶性,在需要时可以配置成溶液进行使用,具有制备简单、适用范围广的优点,易配合其他类型的抗菌技术共同使用。同时,灭菌条件简单,在光照下即可使用,生物相容性好,无毒性等副作用,能保证使用者健康安全。杀菌效果好,杀菌作用时间长,也可以重复使用。
附图说明
图1是实施例7光敏剂S1对金色葡萄球菌和大肠杆菌的抗菌曲线;
图2是实施例8光敏剂S2对金色葡萄球菌和大肠杆菌的抗菌曲线;
图3是实施例9光敏剂S3对金色葡萄球菌和大肠杆菌的抗菌曲线;
图4是实施例10光敏剂S4对金色葡萄球菌和大肠杆菌的抗菌曲线;
图5是实施例11光敏剂S5对金色葡萄球菌和大肠杆菌的抗菌曲线;
图6是实施例12光敏剂S6对金色葡萄球菌和大肠杆菌的抗菌曲线。
具体实施例
下面结合附图和实施例对本发明进一步详细说明,但本发明的保护范围不仅限于这些实施例。
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。
下列实施例中涉及的物料均可从商业渠道获得。
实施例1
光敏剂式S1的合成路线:
(1)在配备有搅拌棒的圆底烧瓶中将2.164g苝四甲酸二酐和1.9738gN,N-二甲基乙二胺1:4混合,再与30g咪唑混合,并用隔垫密封。用氩气吹扫反应容器,然后在130℃下搅拌加热2h。反应结束时,将容器冷却至室温,将内容物悬浮在甲醇中,并使用0.8μm的尼龙膜过滤收集固体。用甲醇洗涤固体,并在真空下干燥,得到纯产物。
(2)在配备有搅拌棒和冷凝器的圆底烧瓶中,将1.8096g步骤(1)得到的化合物和0.84ml碘甲烷混合,再加入100ml氯仿,并回流3h。反应结束时,将混合物冷却至室温,并通过0.8μm的尼龙膜过滤。固体依次用氯仿,乙醚,己烷和乙醇洗涤,并在真空下干燥,得到光敏剂I的纯产物S1。
实施例2
引入电负性取代基-Cl,作为吸电子基团,它将导致所连接分子苯环电子云密度降低,则相对于光敏剂S1而言,所得光敏剂LUMO和HOMO能级将降低,有利于光照后活性氧的产生,增强对细菌的杀灭效果。
光敏剂式S2的合成路线:
(1)在配备有搅拌棒的圆底烧瓶中将2.923g的1,6,7,12-四氯-3,4,9,10-苝四甲酸二酐和1.9738g N,N-二甲基乙二胺1:4混合,再与30g咪唑混合,并用隔垫密封。用氩气吹扫反应容器,然后在130℃下搅拌加热2h。反应结束时,将容器冷却至室温,将内容物悬浮在甲醇中,并使用0.8μm的尼龙膜过滤收集固体。用甲醇洗涤固体,并在真空下干燥,得到纯产物。(2)在配备有搅拌棒和冷凝器的圆底烧瓶中,将2.417g步骤(1)得到的化合物和0.84ml碘甲烷混合,再加入100氯仿,并回流3h。反应结束时,将混合物冷却至室温,并通过0.8μm的尼龙膜过滤。固体依次用氯仿,乙醚,己烷和乙醇洗涤,并在真空下干燥,得到季铵盐苝酰亚胺类化合物纯产物S2。
实施例3
光敏剂3参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将176.05mg化合物a、99.94mg化合物b加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S3。
实施例4
光敏剂4参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将176.05mg化合物a、85.26mg化合物c加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S4。
实施例5
光敏剂5参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将176.05mg化合物a、91.35mg化合物d加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S5。
实施例6
光敏剂6参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将176.05mg化合物a、68.84mg化合物e加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S6。
实施例7
光敏剂7参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将165.64mg化合物f、82.85mg化合物g加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。
2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S7
实施例8
光敏剂8参照按照文献[J.Mater.Chem.A,2019,7,19087.]公开的方法合成。
合成路线如下:
1、将162.10mg化合物h、120.07mg化合物i加入到装有5ml N,N-二甲基甲酰胺(DMF),1.017gK3PO4和23.11mgPd(PPh3)4的圆底烧瓶中。通过用N2鼓泡30分钟使混合物脱气,接着在150℃下加热48小时。2、将混合物冷却至室温,接着倒入水中,过滤收集沉淀物,并用水,甲醇,氯仿和四氢呋喃洗涤。3、通过用THF进行索氏抽提72小时,进一步纯化该聚合物,并将产物减压干燥得到S8
实施例9
在PBS缓冲液中配制20μmol/ml的光敏剂S1溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
实施例10
在PBS缓冲液中配制20μmol/ml的光敏剂S2溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
实施例11
在PBS缓冲液中配制20μmol/ml的光敏剂S3溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
实施例12
在PBS缓冲液中配制20μmol/ml的光敏剂S4溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
实施例13
在PBS缓冲液中配制20μmol/ml的光敏剂S5溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
实施例14
在PBS缓冲液中配制20μmol/ml的光敏剂S6溶液,之后用缓冲液将样品各依次稀释至3μmol/ml、1μmol/ml、0.8μmol/ml,0.5μmol/ml,0.1μmol/ml备用。
将储存在低温的金色葡萄球菌珠和大肠杆菌珠取出,分别用液体培养基扩大培养后,用缓冲液稀释到浓度约为108CFU/ml。
向上述浓度的细菌悬浮液中分别加入不同浓度的光敏剂,每种细菌平行制备两组样品,在避光条件下孵育15min后,一组继续在避光条件下孵育30min,另一组在人工太阳灯下(30mw/cm2)照射10min。
没有添加光敏剂的细菌悬浮液作为对照。
光照和避光处理结束后,将悬浮液用缓冲液稀释105倍,吸取稀释后的各个菌悬液50μl,用涂布棒均匀涂布到90mm的LB营养琼脂平板,倒置后在37℃下培养24h。观察过夜培养后的金色葡萄球菌和大肠杆菌平板培养基,对菌落计数并记录。
由图2和图3结果显示,随着光敏剂浓度升高,抗菌活性明显增强,当光敏剂浓度达到20μg/ml时,对细菌的杀灭率超过70%,这说明本光敏剂对金色葡萄球菌的抗菌活性与光敏剂浓度呈正相关,杀菌浓度极小。图4和图5结果显示,本光敏剂对大肠杆菌的抗菌效果与金色葡萄球菌类似,但是由于大肠杆菌拥有独特外膜结构,对光敏剂起到屏蔽作用,需要更大剂量光敏剂才能达到完全灭菌的效果。在避光条件下,光敏剂的抗菌效果相差较大,说明抗菌能力主要取决于活性氧的生成,而黑暗处理仍然起到抗菌效果的原因是光敏剂结构所含有的季铵盐侧链不仅增加了光敏剂溶解性,同时对于抗菌效果也有一定程度的提高,导致黑暗中也能产生一定的抗菌效果。
实施例15
软膏A:0.01%w/v光敏剂S1及其它合适的药学上可接受的载体。
软膏B:0.01%w/v光敏剂S2及其它合适的药学上可接受的载体。
软膏C:0.01%w/v亚甲基蓝及其合适的药学上可接受的载体,与软膏A和B一致。
首先对接种有念珠菌(107-10CFU/ml)的营养琼脂培养基依次给予光敏药物软膏,接着进行适当条件光照处理,对处理前后各营养培养基的菌落数进行考察,分别考察各光敏药物制剂的杀菌效果。光敏药物软膏样品:软膏A、软膏B、软膏C
光照射处理条件:人工太阳光模拟灯;功率密度:30mW/cm2;照射时间:10min。
空白软膏组不经光照射处理做为阴性对照组。
结果显示:软膏C组没有显示抗微生物活力,软膏B组较软膏A组显示更强的抗微生物效力,这表明:在模拟太阳光照条件下光动力杀菌治疗时,低浓度的亚甲基蓝显示不出抗微生物效果,而光敏剂结合季铵盐基团具有更强的抗微生物活性,其中主链被Cl部分取代的电解质单体表现出最高的抗微生物效果。
实施例16
一种具有杀菌功能的柔性透明薄膜的制备及应用方法,包括以下步骤:
步骤一、依次用去离子水将光敏剂S1、S2、S3和S4配置成1μmol/ml的溶液。
步骤二、将同规格的柔性透明PET板浸入上述溶液中,保持30分钟,取出后于80℃干燥得到杀菌功能的PET板。
步骤三、将制备的有杀菌功能的柔性透明PET板放置于待消毒的平面上,紧密贴合后,采用30mw/cm2辐照强度的模拟太阳光光源照射杀伤细菌。
具有杀菌功能的柔性透明PET板制备简单,流程短,成本低,具有生物相容性,广泛的适用性。该方法制备的薄膜能在食品卫生、医药安全、实验室消毒等领域获得应用。
以上实施例仅为本发明具体实施例的一部分,凡依本发明权利要求书所作的改变,所产生的功能作用未超出本发明权利要求书要求的范围时,均属于本发明的保护范围。
表1专利报道的含抗菌材料MIC值的比较
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