壳聚糖基金纳米棒的构建及其在肿瘤治疗中的应用
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摘要
金纳米棒(gold nanorods、GNRs)具有独特的光、电性能,成为材料学家关注的热点,被越来越多地应用于医学成像、生物检测、基因及药物载体和光热治疗等生物医学研究领域,展现出广阔的应用前景。壳聚糖具有良好的生物相容性、低毒性、可降解性、对生物黏膜较强的粘附性及组织相容性,可用于生物医用材料、基因载体及新型药物传递系统的研究中。尤其是壳聚糖作为抗肿瘤药物载体的研究已经非常广泛。
本文基于GNRs的光热疗以及抗肿瘤药物的化疗,构建了一种毒性低、生物相容性好、适合生物医学领域运用的壳聚糖基金纳米棒杂化材料,实现光热疗-化疗联合治疗肿瘤的目的。主要研究工作如下：
1.合成了不同PEG取代度、不同PEI取代度的壳聚糖衍生物。首先,以聚乙二醇(PEG2000)与丁二酸酐(SA)为原料,合成了双羧基的聚乙二醇化合物(化合物1),通过1H NMR和13C NMR进行结构表征结果显示,合成产物为化合物1且转化完全。同时,由聚乙烯亚胺(PEI)合成了部分巯基化的PEI(化合物2),反应中投料比增加或反应时间延长均会使巯基化程度加深,合成了三种巯基取代度的化合物2,即PEI-SH2、PEI-SH2.4和PEI-SH2.7。以壳聚糖、化合物1和2为原料,通过NHS/EDC催化法分别合成了壳聚糖-PEG衍生物(化合物3)和壳聚糖-PEG-PEI衍生物(化合物4),并通过1HNMR和FT-IR进行结构表征,分别探讨化合物3和化合物4合成过程中投料比对各步产物取代度的影响,随着化合物1和2投料比例的增加取代度增大,但增大到一定程度时不会再出现明显增大,得到了一系列壳聚糖衍生物。
2.合成了长径比可控的金纳米棒(GNRs)并进行了表面修饰。通过晶种生长法合成了GNRs,CTAB包裹于GNRs表面,端位相对裸露巯基优先结合于端位。将化合物2与GNRs混合,通过Au-S键2结合于GNRs表面,透射电镜图可见化合物2与GNRs摩尔比较低时,GNRs以端位连接为主,摩尔比较高时出现部分并肩排列情况。化合物4与GNRs混合,混合液被透析处理所得产物(CS-GNRs)结构以并肩排列为主,且化合物4的PEI取代度高、与GNRs摩尔比高时有利于并肩排列组装形式的出现；混合液被静置处理所得CS-GNRs在摩尔比低时,呈现聚合物被包裹于内部,GNRs排列在外的组装结构,摩尔比高时也出现了并肩排列的趋势。综合产物稳定性、生物相容性等方面,静置条件下的并肩结构更适合用于下一步研究。
3.考察了CS-GNRs用于药物载体研究的性质。以阿霉素(DOX)与化合物4为原料,在NHS/DCC催化下合成了阿霉素-壳聚糖衍生物(DOX-CS,化合物5),参照DOX的浓度-吸光度标准曲线,计算化合物5中DOX取代度为18.4%。通过UV-vis光谱检测表明CS-GNRs的光学稳定性、温度敏感性和激光的稳定性良好,可用于体内外研究。DOX-CS与GNRs偶联产物DOX-CS-GNRs的UV-vis光谱中纵轴吸收峰的位置发生了红移TEM图观察到产物DOX-CS-GNRs为侧面排列的GNRs团簇。
4.体外评价了DOX-CS-GNRs的细胞毒性、细胞摄取以及光热疗-化疗联合抗肿瘤效果。通过细胞毒性实验证明,GNRs在很低浓度便对细胞表现出了很强的毒性作用。CS-GNRs和DOX-CS-GNRs则表现出了较好的生物相容性,细胞毒性很小。DOX-CS-GNRs与肿瘤细胞共同孵育2h后,通过激光共聚焦显微镜在细胞内观察到红色荧光(DOX的荧光)表明,DOX-CS-GNRs已进入了肿瘤细胞。在近红外激光照射条件下,体外评价CS-GNRs对肿瘤细胞的光热疗杀伤作用,DOX-CS-GNRs对肿瘤细胞光热疗-化疗联合治疗作用,结果显示CS-GNRs对肿瘤细胞具有明显的杀伤抑制效果,而DOX-CS-GNRs的杀伤效果更高。以上结果表明,光热疗-化疗的联合治疗作用要比单纯光热疗的治疗作用更强,具有更理想的治疗效果。
综上所述,壳聚糖衍生物与金纳米棒通过Au-S键化学键合方式构建具有特定组装结构的壳聚糖基金纳米棒,同时负载抗肿瘤药物阿霉素,其具有良好的生物相容性和肿瘤杀伤作用,通过光热疗-化疗联合治疗方式比单纯的光热疗具有更强的肿瘤杀伤效果。
Gold nanorods(GNRs) have attracted considerable attention for their unique properties in photothermal therapy, biosensing, molecular imaging, and gene or drug delivery for biomedical applications. Chitosan derivatives are widely used in biomedical materials, gene and drug delivery system with biocompatibility, non-toxicity, biodegradability and strong adhesion of biological mucosa. Expecially, chitosan nanoparticles as a carrier of anticancer drugs has been used very extensively.
In this study, a new hybrid nanomaterials were designed and synthesized based on the conjugates of GNRs and chitosan derivatives with low toxicity and biocompatibility. A synergistic effect of combined photothermo-and chemo-therapy was expected to treat with cancer cells. The main contents of this work are as follows:
1. The chitosan derivatives were designed and synthesized with different substitution degree of PEG and PEI. First, double carboxy-terminated PEG (compound1) was synthesized by esterification of poly(ethylene) glycol (PEG) and succinic acid anhydride (SA). The structure of1was characterized by1H and13C NMR, and the results show that synthetic product was1and transformation completely. Second, partly thioled polyethylenimine (compound2) was prepared by branched polyethylenimine (PEI) and methyl thioglycolate. The degrees of substitution of the thiol moiety determined by Ellman's method were PEI-SH2、PEI-SH2.4and PEI-SH2.7. A modified version of the NHS/EDC coupling approach was used to synthesize PEG2000-g-chitosan conjugate (compound3) and PEI-PEG-g-chitosan conjugate (compound4). The structures of3and4were characterized by1H and13C NMR and FT-IR spectra. The degrees of substitution of the PEG or PEI moiety were influenced by the molar ratio.
2. GNRs were synthesized through seed mediated growth procedure, and the surface was capped by CTAB bilayer while the end faces relatively bare, thus makes the ends much easier to be modified. The2preferentially attached onto the surface of GNRs through Au-S bond. TEM images chearly showed the end-to-end assembly of GNRs when the molar ratio of2and GNRs was low. But with the increae of molar ratios, the side-by-side assembly of GNRs was observed. The chitosan-modified-GNRs nanoparticles (CS-GNRs) were prepared by mixing4and GNRs. The mixture was treated by dialysis and the result was mainly to assemble GNRs into side by side structure. The high degrees of substitution of PEI and high molar ratio of4were suitable for inducing the side by side structure. The CS-GNRs with core-shell structure were prepared by still-setting method when the molar ratio of4and GNRs was low. Chitosan derivatives were wrapped in internal, and GNRs arrayed outside. And the high molar ratio led to side-by-side assembly of GNRs. Therefore, CS-GNRs with side by side structure was more suitable for following research considering the stability and biocompatibility.
3. The CS-GNRs were used for drug delivery system. Doxorubicin (DOX) conjugated to chitosan derivatives by NHS/EDC coupling approach (compound5). The DOX content of5was calculated by fluorescence detection at480nm according to a standard curve of DOX in DMSO, and the degrees of substitution of DOX was18.4%. The stability of optical, temperture and NIR irradiation of CS-GNRs were detected by UV-vis spectra, and the results showed CS-GNRs can be used for following research. The DOX-CS-GNRs with side-by-side structure was prepared by5and GNRs.
4. The raw GNRs showed heavy cytotoxic effect on cells even at low concentration. However, the CS-GNRs and DOX-CS-GNRs did not show any cyctotoxic. The confocal image analysis revealed that DOX-CS-GNRs appeared in cells after incubation for2h. CS-GNRs inhibited cancer cells by photothermal effect under near-infrared laser irradiation. A synergistic effect of DOX-CS-GNRs combined photothermo-and chemo-therapy was found at moderate power intensity of NIR irradiation based on the DOX release and the photothermal effect of GNRs.
In summary, DOX-CS-GNRs was prepared by chitosan derivatives and GNRs through the strong metal sulfur chemical bond between thiols and the surface of GNRs. And the inhibition of DOX-CS-GNRs combined photothermo-and chemo-therapy was more effective than by photothermal therapy alone.
本文基于GNRs的光热疗以及抗肿瘤药物的化疗,构建了一种毒性低、生物相容性好、适合生物医学领域运用的壳聚糖基金纳米棒杂化材料,实现光热疗-化疗联合治疗肿瘤的目的。主要研究工作如下：
1.合成了不同PEG取代度、不同PEI取代度的壳聚糖衍生物。首先,以聚乙二醇(PEG2000)与丁二酸酐(SA)为原料,合成了双羧基的聚乙二醇化合物(化合物1),通过1H NMR和13C NMR进行结构表征结果显示,合成产物为化合物1且转化完全。同时,由聚乙烯亚胺(PEI)合成了部分巯基化的PEI(化合物2),反应中投料比增加或反应时间延长均会使巯基化程度加深,合成了三种巯基取代度的化合物2,即PEI-SH2、PEI-SH2.4和PEI-SH2.7。以壳聚糖、化合物1和2为原料,通过NHS/EDC催化法分别合成了壳聚糖-PEG衍生物(化合物3)和壳聚糖-PEG-PEI衍生物(化合物4),并通过1HNMR和FT-IR进行结构表征,分别探讨化合物3和化合物4合成过程中投料比对各步产物取代度的影响,随着化合物1和2投料比例的增加取代度增大,但增大到一定程度时不会再出现明显增大,得到了一系列壳聚糖衍生物。
2.合成了长径比可控的金纳米棒(GNRs)并进行了表面修饰。通过晶种生长法合成了GNRs,CTAB包裹于GNRs表面,端位相对裸露巯基优先结合于端位。将化合物2与GNRs混合,通过Au-S键2结合于GNRs表面,透射电镜图可见化合物2与GNRs摩尔比较低时,GNRs以端位连接为主,摩尔比较高时出现部分并肩排列情况。化合物4与GNRs混合,混合液被透析处理所得产物(CS-GNRs)结构以并肩排列为主,且化合物4的PEI取代度高、与GNRs摩尔比高时有利于并肩排列组装形式的出现；混合液被静置处理所得CS-GNRs在摩尔比低时,呈现聚合物被包裹于内部,GNRs排列在外的组装结构,摩尔比高时也出现了并肩排列的趋势。综合产物稳定性、生物相容性等方面,静置条件下的并肩结构更适合用于下一步研究。
3.考察了CS-GNRs用于药物载体研究的性质。以阿霉素(DOX)与化合物4为原料,在NHS/DCC催化下合成了阿霉素-壳聚糖衍生物(DOX-CS,化合物5),参照DOX的浓度-吸光度标准曲线,计算化合物5中DOX取代度为18.4%。通过UV-vis光谱检测表明CS-GNRs的光学稳定性、温度敏感性和激光的稳定性良好,可用于体内外研究。DOX-CS与GNRs偶联产物DOX-CS-GNRs的UV-vis光谱中纵轴吸收峰的位置发生了红移TEM图观察到产物DOX-CS-GNRs为侧面排列的GNRs团簇。
4.体外评价了DOX-CS-GNRs的细胞毒性、细胞摄取以及光热疗-化疗联合抗肿瘤效果。通过细胞毒性实验证明,GNRs在很低浓度便对细胞表现出了很强的毒性作用。CS-GNRs和DOX-CS-GNRs则表现出了较好的生物相容性,细胞毒性很小。DOX-CS-GNRs与肿瘤细胞共同孵育2h后,通过激光共聚焦显微镜在细胞内观察到红色荧光(DOX的荧光)表明,DOX-CS-GNRs已进入了肿瘤细胞。在近红外激光照射条件下,体外评价CS-GNRs对肿瘤细胞的光热疗杀伤作用,DOX-CS-GNRs对肿瘤细胞光热疗-化疗联合治疗作用,结果显示CS-GNRs对肿瘤细胞具有明显的杀伤抑制效果,而DOX-CS-GNRs的杀伤效果更高。以上结果表明,光热疗-化疗的联合治疗作用要比单纯光热疗的治疗作用更强,具有更理想的治疗效果。
综上所述,壳聚糖衍生物与金纳米棒通过Au-S键化学键合方式构建具有特定组装结构的壳聚糖基金纳米棒,同时负载抗肿瘤药物阿霉素,其具有良好的生物相容性和肿瘤杀伤作用,通过光热疗-化疗联合治疗方式比单纯的光热疗具有更强的肿瘤杀伤效果。
Gold nanorods(GNRs) have attracted considerable attention for their unique properties in photothermal therapy, biosensing, molecular imaging, and gene or drug delivery for biomedical applications. Chitosan derivatives are widely used in biomedical materials, gene and drug delivery system with biocompatibility, non-toxicity, biodegradability and strong adhesion of biological mucosa. Expecially, chitosan nanoparticles as a carrier of anticancer drugs has been used very extensively.
In this study, a new hybrid nanomaterials were designed and synthesized based on the conjugates of GNRs and chitosan derivatives with low toxicity and biocompatibility. A synergistic effect of combined photothermo-and chemo-therapy was expected to treat with cancer cells. The main contents of this work are as follows:
1. The chitosan derivatives were designed and synthesized with different substitution degree of PEG and PEI. First, double carboxy-terminated PEG (compound1) was synthesized by esterification of poly(ethylene) glycol (PEG) and succinic acid anhydride (SA). The structure of1was characterized by1H and13C NMR, and the results show that synthetic product was1and transformation completely. Second, partly thioled polyethylenimine (compound2) was prepared by branched polyethylenimine (PEI) and methyl thioglycolate. The degrees of substitution of the thiol moiety determined by Ellman's method were PEI-SH2、PEI-SH2.4and PEI-SH2.7. A modified version of the NHS/EDC coupling approach was used to synthesize PEG2000-g-chitosan conjugate (compound3) and PEI-PEG-g-chitosan conjugate (compound4). The structures of3and4were characterized by1H and13C NMR and FT-IR spectra. The degrees of substitution of the PEG or PEI moiety were influenced by the molar ratio.
2. GNRs were synthesized through seed mediated growth procedure, and the surface was capped by CTAB bilayer while the end faces relatively bare, thus makes the ends much easier to be modified. The2preferentially attached onto the surface of GNRs through Au-S bond. TEM images chearly showed the end-to-end assembly of GNRs when the molar ratio of2and GNRs was low. But with the increae of molar ratios, the side-by-side assembly of GNRs was observed. The chitosan-modified-GNRs nanoparticles (CS-GNRs) were prepared by mixing4and GNRs. The mixture was treated by dialysis and the result was mainly to assemble GNRs into side by side structure. The high degrees of substitution of PEI and high molar ratio of4were suitable for inducing the side by side structure. The CS-GNRs with core-shell structure were prepared by still-setting method when the molar ratio of4and GNRs was low. Chitosan derivatives were wrapped in internal, and GNRs arrayed outside. And the high molar ratio led to side-by-side assembly of GNRs. Therefore, CS-GNRs with side by side structure was more suitable for following research considering the stability and biocompatibility.
3. The CS-GNRs were used for drug delivery system. Doxorubicin (DOX) conjugated to chitosan derivatives by NHS/EDC coupling approach (compound5). The DOX content of5was calculated by fluorescence detection at480nm according to a standard curve of DOX in DMSO, and the degrees of substitution of DOX was18.4%. The stability of optical, temperture and NIR irradiation of CS-GNRs were detected by UV-vis spectra, and the results showed CS-GNRs can be used for following research. The DOX-CS-GNRs with side-by-side structure was prepared by5and GNRs.
4. The raw GNRs showed heavy cytotoxic effect on cells even at low concentration. However, the CS-GNRs and DOX-CS-GNRs did not show any cyctotoxic. The confocal image analysis revealed that DOX-CS-GNRs appeared in cells after incubation for2h. CS-GNRs inhibited cancer cells by photothermal effect under near-infrared laser irradiation. A synergistic effect of DOX-CS-GNRs combined photothermo-and chemo-therapy was found at moderate power intensity of NIR irradiation based on the DOX release and the photothermal effect of GNRs.
In summary, DOX-CS-GNRs was prepared by chitosan derivatives and GNRs through the strong metal sulfur chemical bond between thiols and the surface of GNRs. And the inhibition of DOX-CS-GNRs combined photothermo-and chemo-therapy was more effective than by photothermal therapy alone.
引文
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