人工晶体学报, 2023, 52 (3): 510, 网络出版: 2023-04-13  

单羟基咔咯的合成、晶体的生长和光动力抗菌活性研究

Synthesis, Crystal Growth and Photodynamic Antibacterial Activity of Monohydroxy Corrole
作者单位
1 广东第二师范学院化学与材料科学学院, 广州 510800
2 广东第二师范学院生物与食品工程学院, 广州 510303
3 佛山市第四人民医院结核科, 佛山 528041
摘要
光动力抗菌疗法(PDAT)是一种新型的治疗微生物感染的手段, 咔咯在光动力抗肿瘤方面具有显著优势, 但在光动力抗菌方面却鲜有报道。本文合成了单羟基咔咯即10-(4-羟基苯基)-5, 15-二(2, 3, 4, 5, 6-五氟苯基)咔咯(P-OH), 并进一步研究其晶体结构和光动力抗菌活性。结果表明, 单羟基咔咯属于正交晶系, 具有良好的光动力抗菌活性, 药物浓度大于2MIC时其显示出杀菌作用, 药物浓度小于2MIC时其显示出抑菌作用, 其最低杀菌浓度和最低抑菌浓度皆比卟啉低, 是一种良好的光动力抗菌光敏剂。
Abstract
Photodynamic antimicrobial therapy (PDAT) is a new method for the treatment of microbial infections. However, there have been few reports on the photodynamic antimicrobial activity of corrole, which has a significant advantage in the treatment of photodynamic antitumor activity. In this study, mono-hydroxyl corrole named 10-(4-hydroxyphenyl)-5, 15-bis(pentafluorophenyl) corrole (P-OH) was synthesized. What’s more, its crystal structure and photodynamic antibacterial activity were also explored. The results indicate that mono-hydroxyl corrole belongs to orthorhombic crystal system and shows good photodynamic antibacterial activity. When the concentration of the drug is more than 2MIC, the bacteriostatic effect is showed. Whereas, the concentration of drug less than 2MIC shows antibacterial effect. The minimum bactericidal concentration and minimum inhibitory concentration of the drug are lower than porphyrin, it is a good photodynamic antibacterial photosensitizer.
参考文献

[1] 雷尚雪, 但红霞. 光动力治疗增效研究新进展[J]. 口腔医学研究, 2022, 38(6): 497-500.

[2] 庞家胤, 和亚雄, 郑梦雪, 等. 光动力抗菌疗法对多重耐药铜绿假单胞菌体外杀伤作用的研究[J]. 第三军医大学学报, 2021, 43(7): 599-605.

[3] 董建成. 纤维素基/卟啉光敏材料的制备及其抗菌性能[D]. 无锡: 江南大学, 2019.

[4] 孙艳梅. 单羟基咔咯及其金属配合物的光动力抗肿瘤活性研究[D]. 广州: 华南理工大学, 2020.

[5] JIA Q Y, SONG Q, LI P, et al. Rejuvenated photodynamic therapy for bacterial infections[J]. Advanced Healthcare Materials, 2019, 8(14): 1900608.

[6] 赵建喜, 尹秀娟, 方子源, 等. 光动力抗菌治疗骨髓炎的研究进展[J]. 河北大学学报(自然科学版), 2022, 42(2): 199-207.

[7] 孙玉洁, 高敏政, 朱艺文, 等.光动力抗菌高分子材料研究进展[J]. 中国材料进展, 2022, 41(7):508-519+507.

[8] 张 静, 赵 天, 丁亚楠, 等. 三羟基咔咯及其镓配合物(-Ga)在新型抗肿瘤药物研发中的应用及对人肺癌细胞(A549)增殖的影响[J]. 新疆医科大学学报, 2021, 44(3): 315-320.

[9] 张 振, 温俊霞, 张生玉, 等. Push-Pull型不对称钴(Ⅲ)咔咯的合成与性质[J]. 合成化学, 2020, 28(9): 759-763.

[10] 汪华华. 乙氧基羰基取代卟啉与咔咯金属配合物的研究[D]. 广州:华南理工大学, 2017.

[11] 阳 红, 邹怀波, 汪华华, 等. 不同取代基铁咔咯配合物对苯乙烯的催化氧化[J]. 无机化学学报, 2015, 31(5): 968-974.

[12] LI X L, ZHANG X P, GUO M, et al. Identifying intermediates in electrocatalytic water oxidation with a manganese corrole complex[J]. Journal of the American Chemical Society, 2021, 143(36): 14613-14621.

[13] 蒋 笑. 羟基咔咯磷配合物与DNA的相互作用及光动力抗肿瘤活性研究[D]. 广州: 华南理工大学, 2020.

[14] 张 召, 余华军, 黄 慧, 等.咔咯光动力靶向降解SIRT1调节蛋白质乙酰化修饰抑制肝癌细胞生长的分子机制探究[C]//第十一届全国化学生物学学术会议论文摘要(第二卷). 广州, 2019: 256.

[15] 冀晓宁. 咔咯及其衍生物的合成与性质研究[D]. 南京: 南京大学, 2013.

[16] 李仕成, 方玉琦, 郭峻彤, 等. 溴乙基取代镓(Ⅲ)咔咯的合成及荧光性质研究[J]. 山东化工, 2020, 49(14):24-26+30.

[17] ZHAO Y M, DAI W H, PENG Y L, et al. A corrole-based covalent organic framework featuring desymmetrized topology[J]. Angewandte Chemie International Edition, 2020, 59(11): 4354-4359.

[18] EINREM R F, ALEMAYEHU A B, BORISOV S M, et al. Amphiphilic rhenium-oxo corroles as a new class of sensitizers for photodynamic therapy[J]. ACS Omega, 2020, 5(18): 10596-10601.

[19] LIM P, MAHAMMED A, OKUN Z, et al. Differential cytostatic and cytotoxic action of metallocorroles against human cancer cells: potential platforms for anticancer drug development[J]. Chemical Research in Toxicology, 2012, 25(2): 400-409.

[20] AGADJANIAN H, MA J, RENTSENDORJ A, et al. Tumor detection and elimination by a targeted gallium corrole[J]. Proceedings of the National Academy of Sciences of the United States of America, 2009, 106(15): 6105-6110.

[21] TEO R D, GRAY H B, LIM P, et al. A cytotoxic and cytostatic gold(Ⅲ) corrole[J]. Chemical Communications, 2014, 50(89): 13789-13792.

[22] ZHANG Z, YU H J, HUANG H, et al. The photocytotoxicity effect of cationic sulfonated corrole towards lung cancer cells: in vitro and in vivo study[J]. Lasers in Medical Science, 2019, 34(7): 1353-1363.

[23] NA N, ZHAO D Q, LI H, et al. DNA binding, photonuclease activity and human serum albumin interaction of a water-soluble freebase carboxyl corrole[J]. Molecules, 2015, 21(1): E54.

[24] 史 蕾, 杨文聪, 沈 淇, 等.咔咯铁(Ⅲ)配合物与DNA的作用及其抗肿瘤活性[J]. 应用化学, 2019, 36(12): 1376-1386.

[25] 孙艳梅, 刘海洋. 对羟基咔咯的细胞毒性研究[C]//全国第十九届大环化学暨第十一届超分子化学学术讨论会摘要论文集.呼伦贝尔, 2018:403.

[26] CARDOTE T A F, BARATA J F B, AMADOR C, et al. Evaluation of meso-substituted cationic corroles as potential antibacterial agents[J]. Anais Da Academia Brasileira De Ciencias, 2018, 90(1 Suppl 2): 1175-1185.

[27] PREU A, SALTSMAN I, MAHAMMED A, et al. Photodynamic inactivation of mold fungi spores by newly developed charged corroles[J]. Journal of Photochemistry and Photobiology B: Biology, 2014, 133: 39-46.

[28] 秦银辉. 新型N-11, C-12, C-13和C-9位芳烷基克拉霉素半合成衍生物的设计、合成及生物活性评价[D]. 济南: 山东大学, 2020.

[29] 潘吉脉, 胡安东, 杨 霞, 等. 9味中药及其组方对鱼源弗氏柠檬酸杆菌体外抑菌试验的研究[J]. 扬州大学学报(农业与生命科学版), 2019, 40(4): 80-83.

[30] AMOS-TAUTUA B M, SONGCA S P, OLUWAFEMI O S. Application of porphyrins in antibacterial photodynamic therapy[J]. Molecules (Basel, Switzerland), 2019, 24(13): 2456.

[31] 史 蕾. Corrole单体及其吩噻嗪二元体的合成、光谱性质和光断裂DNA性质研究[D]. 广州: 华南理工大学, 2010.

吴淑琼, 何裕良, 郑嘉琪, 黄婉瑜, 陈培妮, 莫晓琳, 叶嘉欣, 欧晓倩, 林佳颖, 郭惠琳, 黄慧琳, 许逸戈, 史蕾, 佘婷婷, 钟永辉. 单羟基咔咯的合成、晶体的生长和光动力抗菌活性研究[J]. 人工晶体学报, 2023, 52(3): 510. WU Shuqiong, HE Yuliang, ZHENG Jiaqi, HUANG Wanyu, CHEN Peini, MO Xiaolin, YE Jiaxin, OU Xiaoqian, LIN Jiaying, GUO Huilin, HUANG Huilin, XU Yige, SHI Lei, SHE Tingting, ZHONG Yonghui. Synthesis, Crystal Growth and Photodynamic Antibacterial Activity of Monohydroxy Corrole[J]. Journal of Synthetic Crystals, 2023, 52(3): 510.

关于本站 Cookie 的使用提示

中国光学期刊网使用基于 cookie 的技术来更好地为您提供各项服务,点击此处了解我们的隐私策略。 如您需继续使用本网站,请您授权我们使用本地 cookie 来保存部分信息。
全站搜索
您最值得信赖的光电行业旗舰网络服务平台!