Controlled Release of Carbon Monoxide Based on Nanomaterials and Their Biomedical Applications
Received date: 2018-12-17
Online published: 2019-02-14
Supported by
Project supported by the National Basic Research Programs of China (Nos. 2016YFA0201600, 2016YFA0202104), the National Natural Science Foundation of China (Nos. 51822207, 51772292, 31571015, 11621505, 11435002, 81703071) and Youth Innovation Promotion Association of Chinese Academy of Sciences (No. 2013007) and Chongqing Basic and Frontier Research Program (No. cstc2016jcyjA0279) and Military Medical Science and Technology Innovation Program of Southwest Hospital (Nos. SWH2016LHJC-07, SWH2016JCYB-01 and SWH2017YQPY-03).
In recent years, the use of gas therapy has been more and more concerned by researchers in biomedical applications. Carbon monoxide (CO) is a diatomic gas messenger molecule with the function of transmitting intercellular information and regulating cellular signals. CO is found to play an extremely important physiological role in multiple systems, including cardiovascular system, nervous system, immune system, endocrine system and respiratory system, cancer therapy, coagulation and fibrinolysis system, organ transplantation and preservation, and so on. The biological functions of carbon monoxide molecule greatly depend on the its concentration, position, and duration. However, the existing carbon monoxide donors including Mn2(CO)10, Ru2Cl4(CO)6, Ru(CO)3Cl(glycinato), CORM-F, CORM-A1 have some disadvantages, such as poor stability, difficulties in dose control, lack of targeting, potential toxic and side effects on normal cells and tissues, which limited their further applications. How to control the concentration of carbon monoxide in the specific region has always been a big challenge in the field of biomedical applications. With the rapid development of nanoscience and technology, researchers have constructed a series of multifunctional carbon monoxide releasing nanomaterials, provided a new idea for CO controlled release, and applied them in the field of biomedicine. In this paper, several kinds of endogenous/exogenous stimulus-responsive CO releasing nanomaterials with the unique advantages are introduced based on the stimuli source. Then, the applications of these controlled CO releasing nanomaterials in biomedical fields, such as inhibiting inflammation, anti-bacte- rial and cancer therapy, are summarized. Finally, the challenges and prospects of CO releasing nanomaterials are discussed.
Zhang Xiaolei , Tian Gan , Zhang Xia , Wang Qing , Gu Zhanjun . Controlled Release of Carbon Monoxide Based on Nanomaterials and Their Biomedical Applications[J]. Acta Chimica Sinica, 2019 , 77(5) : 406 -417 . DOI: 10.6023/A18120504
[1] Queiroga, C. S.; Almeida, A. S.; Vieira, H. L. Biochem. Res. Int. 2012, 2012, 749845.
[2] Haldane, J. B. S. Biochem. J. 1927, 21, 1068.
[3] Turner, M.; Hamilton-Farrell, M. R.; Clark, R. J. J. Accid. Emerg. Med. 1999, 16, 92.
[4] Untereiner, A. A.; Wu, L.; Wang, R. Gasotransmitters:Physiology and Pathophysiology, Hermann, A.; Sitdikova, G. F.; Weiger, T. M., Berlin, Heidelberg, Springer, 2012, pp. 37~70.
[5] Coburn, R. F. N. Engl. J. Med. 1970, 282, 207.
[6] Douglas, C. G.; Haldane, J. S.; Haldane, J. B. J. Physiol. 1912, 44, 275.
[7] Slebos, D. J.; Ryter, S. W.; Choi, A. M. Respir. Res. 2003, 4, 7.
[8] Foresti, R.; Hammad, J.; Clark, J. E.; Johnson, T. R.; Mann, B. E.; Friebe, A.; Green, C. J.; Motterlini, R. Br. J. Pharmacol. 2004, 142, 453.
[9] Ma, X. L.; Sayed, N.; Beuve, A.; van den Akker, F. EMBO J. 2007, 26, 578.
[10] Rodriguez, A. I.; Gangopadhyay, A.; Kelley, E. E.; Pagano, P. J.; Zuckerbraun, B. S.; Bauer, P. M. Arterioscler. Thromb. Vasc. Biol. 2010, 30, 98.
[11] Garcia-Gallego, S.; Bernardes, G. J. Angew. Chem., Int. Ed. 2014, 53, 9712.
[12] Donegan, S. E.; Naples, K. M. Cancer Pract. 2002, 10, 53.
[13] Ling, K.; Men, F.; Wang, W. C.; Zhou, Y. Q.; Zhang, H. W.; Ye, D. W. J. Med. Chem. 2018, 61, 2611.
[14] Motterlini, R.; Clark, J. E.; Foresti, R.; Sarathchandra, P.; Mann, B. E.; Green, C. J. Circ. Res. 2002, 90, E17.
[15] Zuckerbraun, B. S.; Chin, B. Y.; Bilban, M.; d'Avila, J. C.; Rao, J.; Billiar, T. R.; Otterbein, L. E. FASEB J. 2007, 21, 1099.
[16] Parr, S. R.; Wilson, M. T.; Greenwood, C. Biochem. J. 1975, 151, 51.
[17] Brunori, M.; Parr, S. R.; Greenwood, C.; Wilson, M. T. Biochem. J. 1975, 151, 185.
[18] Gorman, D.; Drewry, A.; Huang, Y. L.; Sames, C. Toxicol. 2003, 187, 25.
[19] Pitchumony, T. S.; Spingler, B.; Motterlini, R.; Alberto, R. Chimia 2008, 62, 277.
[20] Motterlini, R.; Otterbein, L. E. Nat. Rev. Drug Discovery 2010, 9, 728.
[21] Sawle, P.; Foresti, R.; Mann, B. E.; Johnson, T. R.; Green, C. J.; Motterlini, R. Br. J. Pharmacol. 2005, 145, 800.
[22] Inaba, H.; Fujita, K.; Ueno, T. Biomater. Sci. 2015, 3, 1423.
[23] Li, Y.; Shu, Y. Z.; Liang, M. W.; Xie, X. L.; Jiao, X. Y.; Wang, X.; Tang, B. Angew. Chem. Int. Ed. 2018, 57, 12415.
[24] Sanvicens, N.; Marco, M. P. Trends Biotechnol. 2008, 26, 425.
[25] Bahrami, B.; Hojjat-Farsangi, M.; Mohammadi, H.; Anvari, E.; Ghalamfarsa, G.; Yousefi, M.; Jadidi-Niaragh, F. Immunol. Lett. 2017, 190, 64.
[26] Ding, C. Z.; Li, Z. B. Mater. Sci. Eng., C 2017, 76, 1440.
[27] Wang, Z. Q.; Ciacchi, L. C.; Wei, G. Appl. Sci. 2017, 7, 1175.
[28] Gu, Z. J.; Zhu, S.; Yan, L.; Zhao, F.; Zhao, Y. L. Adv. Mater. 2018, 1800662.
[29] Kemp, J. A.; Shim, M. S.; Heo, C. Y.; Kwon, Y. J. Adv. Drug Delivery Rev. 2016, 98, 3.
[30] Blum, A. P.; Kammeyer, J. K.; Rush, A. M.; Callmann, C. E.; Hahn, M. E.; Gianneschi, N. C. J. Am. Chem. Soc. 2015, 137, 2140.
[31] Mo, R.; Gu, Z. Mater. Today 2016, 19, 274.
[32] Gulzar, A.; Gai, S. L.; Yang, P. P.; Li, C. X.; Ansari, M. B.; Lin, J. J. Mater. Chem. B 2015, 3, 8599.
[33] Swietach, P.; Vaughan-Jones, R. D.; Harris, A. L.; Hulikova, A. Phil. Trans. R. Soc. B 2014, 369, 20130099.
[34] Kato, Y.; Ozawa, S.; Miyamoto, C.; Maehata, Y.; Suzuki, A.; Maeda, T.; Baba, Y. Cancer Cell Int. 2013, 13, 89.
[35] He, Q. J. Biomater. Sci. 2017, 5, 2226.
[36] Fan, W.; Yung, B. C.; Chen, X. Angew. Chem., Int. Ed. 2018, 57, 8383.
[37] Jin, Q.; Deng, Y. Y.; Jia, F.; Tang, Z.; Ji, J. Adv. Therap. 2018, 1800084.
[38] Yin, X. F.; Liu, X. H.; Shen, L. H.; Jin, H.; Yang, P. Y. Acta Chim. Sinica 2015, 73, 337. (殷薛飞, 刘晓慧, 申华莉, 金红, 杨芃原, 化学学报, 2015, 73, 337.)
[39] Kim, C. K.; Lim, S. J. Arch. Pharm. Res. 2002, 25, 229.
[40] Li, Z. T.; Yu, G. C.; Yang, J. Org. Chem. Front. 2017, 4, 115.
[41] Zhou, L. X. Acta Chim. Sinica 2017, 75, 552. (周立祥, 化学学报, 2017, 75, 552.)
[42] Shao, W.; Liu, X.; Wang, T. T.; Hu, X. Y. Chin. J. Org. Chem. 2018, 38, 1107. (邵为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 38, 1107.)
[43] Zhang, B.; Chang, B. S.; Sun, T. L. Acta Chim. Sinica 2018, 76, 35. (张蓓, 常柏松, 孙涛垒, 化学学报, 2018, 76, 35.)
[44] Li, Z. Y.; Hu, X. Y.; Jiang, J. L.; Zhang, D. M.; Xiao, S. J.; Lin, C.; Wang, L. Y. Chin. J. Org. Chem. 2018, 38, 29. (李臻益, 胡晓玉, 强琚莉, 张冬梅, 肖守军, 林晨, 王乐勇, 有机化学, 2018, 38, 29.)
[45] Motterlini, R.; Sawle, P.; Hammad, J.; Bains, S.; Alberto, R.; Foresti, R.; Green, C. J. FASEB J. 2005, 19, 284.
[46] Chang, Y. J.; Liu, X. Z.; Zhao, Q.; Yang, X. H.; Wang, K. M.; Wang, Q.; Lin, M.; Yang, M. Chin. Chem. Lett. 2015, 26, 1203.
[47] Gu, Z.; Dang, T. T.; Ma, M.; Tang, B. C.; Cheng, H.; Jiang, S.; Dong, Y.; Zhang, Y.; Anderson, D. G. ACS Nano 2013, 7, 6758.
[48] Nguyen, D.; Adnan, N. N.; Oliver, S.; Boyer, C. Macromol. Rapid Commun. 2016, 37, 739.
[49] Lopez-Lazaro, M. FASEB J. 2006, 20, 828.
[50] Fan, W. P.; Bu, W. B.; Shen, B.; He, Q. J.; Cui, Z. W.; Liu, Y. Y.; Zheng, X. P.; Zhao, K. L.; Shi, J. L. Adv. Mater. 2015, 27, 4155.
[51] Liu, T. P.; Wu, S. H.; Chen, Y. P.; Chou, C. M.; Chen, C. T. Nanoscale 2015, 7, 6471.
[52] Suliman, H. B.; Carraway, M. S.; Tatro, L. G.; Piantadosi, C. A. J. Cell Sci. 2007, 120, 299.
[53] Veal, E. A.; Day, A. M.; Morgan, B. A. Mol. Cell 2007, 26, 1.
[54] Tsan, M. F. Int. J. Mol. Med. 2001, 7, 13.
[55] Senturker, S.; Karahalil, B.; Inal, M.; Yilmaz, H.; Muslumanoglu, H.; Gedikoglu, G.; Dizdaroglu, M. FEBS Lett. 1997, 416, 286.
[56] Jin, Z. K.; Wen, Y. Y.; Xiong, L. W.; Yang, T.; Zhao, P. H.; Tan, L. W.; Wang, T. F.; Qian, Z. Y.; Su, B. L.; He, Q. J. Chem. Commun. 2017, 53, 5557.
[57] Jin, Z. K.; Zhao, P. H.; Zhang, J. H.; Yang, T.; Zhou, G. X.; Zhang, D. H.; Wang, T. F.; He, Q. J. Chem. Eur. J. 2018, 24, 11667.
[58] Wu, L. H.; Cai, X. J.; Zhu, H. F.; Li, J. H.; Shi, D. X.; Su, D. F.; Yue, D.; Gu, Z. W. Adv. Funct. Mater. 2018, 28, 1804324.
[59] He, Q. J.; Chen, D. Y.; Fan, M. J. J. Inorg. Mater. 2018, 33, 811. (何前军, 陈丹阳, 范明俭, 无机材料学报, 2018, 33, 811.)
[60] Gonzales, M. A.; Han, H.; Moyes, A.; Radinos, A.; Hobbs, A. J.; Coombs, N.; Oliver, S. R. J.; Mascharak, P. K. J. Mater. Chem. B 2014, 2, 2107.
[61] Govender, P.; Pai, S.; Schatzschneider, U.; Smith, G. S. Inorg. Chem. 2013, 52, 5470.
[62] Bohlender, C.; Glaser, S.; Klein, M.; Weisser, J.; Thein, S.; Neugebauer, U.; Popp, J.; Wyrwa, R.; Schiller, A. J. Mater. Chem. B 2014, 2, 1454.
[63] Bruckmann, N. E.; Wahl, M.; Reiss, G. J.; Kohns, M.; Watjen, W.; Kunz, P. C. Eur. J. Inorg. Chem. 2011, 2011, 4571.
[64] Popova, M.; Soboleva, T.; Ayad, S.; Benninghoff, A. D.; Berreau, L. M. J. Am. Chem. Soc. 2018, 140, 9721.
[65] Fujita, K.; Tanaka, Y.; Abe, S.; Ueno, T. Angew. Chem., Int. Ed. 2016, 55, 1056.
[66] Dordelmann, G.; Meinhardt, T.; Sowik, T.; Krueger, A.; Schatzschneider, U. Chem. Commun. 2012, 48, 11528.
[67] Carmona, F. J.; Jimenez-Amezcua, I.; Rojas, S.; Romao, C. C.; Navarro, J. A. R.; Maldonado, C. R.; Barea, E. Inorg. Chem. 2017, 56, 10474.
[68] Chakraborty, I.; Carrington, S. J.; Hauser, J.; Oliver, S. R. J.; Mascharak, P. K. Chem. Mater. 2015, 27, 8387.
[69] Zhang, X. D.; Tian, H.; He, J. H.; Cao, Y. Acta Chim. Sinica 2013, 71, 433. (张晓丹, 田华, 贺军辉, 曹阳, 化学学报, 2013, 71, 433.)
[70] Diring, S.; Carne-Sanchez, A.; Zhang, J.; Ikemura, S.; Kim, C.; Inaba, H.; Kitagawa, S.; Furukawa, S. Chem. Sci. 2017, 8, 2381.
[71] Pierri, A. E.; Huang, P. J.; Garcia, J. V.; Stanfill, J. G.; Chui, M.; Wu, G.; Zheng, N.; Ford, P. C. Chem. Commun. 2015, 51, 2072.
[72] Askes, S. H. C.; Reddy, G. U.; Wyrwa, R.; Bonnet, S.; Schiller, A. J. Am. Chem. Soc. 2017, 139, 15292.
[73] He, Q. J.; Kiesewetter, D. O.; Qu, Y.; Fu, X.; Fan, J.; Huang, P.; Liu, Y. J.; Zhu, G. Z.; Liu, Y.; Qian, Z. Y.; Chen, X. Y. Adv. Mater. 2015, 27, 6741.
[74] Tan, M. J.; Pan, H. C.; Tan, H. R.; Chai, J. W.; Lim, Q. F.; Wong, T. I.; Zhou, X.; Hong, Z. Y.; Liao, L. D.; Kong, K. V. Adv. Healthcare Mater. 2018, 7, 1870022.
[75] Wei, Z. J.; Liu, G. X.; Dong, X. T.; Wang, J. X.; Yu, W. S. Acta Chim. Sinica 2014, 72, 257. (魏忠杰, 刘桂霞, 董相廷, 王进贤, 于文生, 化学学报, 2014, 72, 257.)
[76] Zhang, X.; Guo, Z.; Liu, J.; Tian, G.; Chen, K.; Yu, S. C.; Gu, Z. J. Sci. Bull. 2017, 62, 985.
[77] Chen, H. B.; Gu, Z. J.; An, H. W.; Chen, C. Y.; Chen, J.; Cui, R.; Chen, S. Q.; Chen, W. H.; Chen, X. S.; Chen, X. Y.; Chen, Z.; Ding, B. Q.; Dong, Q.; Fan, Q.; Fu, T.; Hou, D. Y.; Jiang, Q.; Ke, H. T.; Jiang, X. Q.; Liu, G.; Li, S. P.; Li, T. Y.; Liu, Z.; Nie, G. J.; Ovais, M.; Pang, D. W.; Qiu, N. S.; Shen, Y. Q.; Tian, H. Y.; Wang, C.; Wang, H.; Wang, Z. Q.; Xu, H. P.; Xu, J. F.; Yang, X. L.; Zhu, S.; Zheng, X. C.; Zhang, X. Z.; Zhao, Y. B.; Tan, W. H.; Zhang, X.; Zhao, Y. L. Sci. China Chem. 2018, 61, 1503.
[78] Lin, X. Y.; Wang, J. Acta Chim. Sinica 2017, 75, 979(in Chinese). (林潇羽, 王璟, 化学学报, 2017, 75, 979.)
[79] Li, W. P.; Su, C. H.; Tsao, L. C.; Chang, C. T.; Hsu, Y. P.; Yeh, C. S. ACS Nano 2016, 10, 11027.
[80] Cole, A. J.; Yang, V. C.; David, A. E. Trends Biotechnol. 2011, 29, 323.
[81] Williams, P. S.; Carpino, F.; Zborowski, M. Mol. Pharmaceutics 2009, 6, 1290.
[82] Pankhurst, Q. A.; Connolly, J.; Jones, S. K.; Dobson, J. J. Phys. D: Appl. Phys. 2003, 36, R167.
[83] Kunz, P. C.; Meyer, H.; Barthel, J.; Sollazzo, S.; Schmidt, A. M.; Janiak, C. Chem. Commun. 2013, 49, 4896.
[84] Meyer, H.; Winkler, F.; Kunz, P.; Schmidt, A. M.; Hamacher, A.; Kassack, M. U.; Janiak, C. Inorg. Chem. 2015, 54, 11236.
[85] Stone, J. R.; Marletta, M. A. Biochemistry 1994, 33, 5636.
[86] Botros, F. T.; Navar, L. G. Am. J. Physiol. Heart Circ. Physiol. 2006, 291, H2772.
[87] Ramos, K. S.; Lin, H.; McGrath, J. J. Biochem. Pharmacol. 1989, 38, 1368.
[88] Li, A. L.; Xi, Q.; Umstot, E. S.; Bellner, L.; Schwartzman, M. L.; Jaggar, J. H.; Leffler, C. W. Circ. Res. 2008, 102, 234.
[89] Song, Y. C.; Liu, J. X.; Zhang, Y. Y.; Shi, W.; Ma, H. M. Acta Chim. Sinica 2013, 71, 1607. (宋延超, 刘俊秀, 张阳阳, 史文, 马会民, 化学学报, 2013, 71, 1607.)
[90] Otterbein, L. E.; Bach, F. H.; Alam, J.; Soares, M.; Lu, H. T.; Wysk, M.; Davis, R. J.; Flavell, R. A.; Choi, A. M. Nat. Med. 2000, 6, 422.
[91] Lee, T. S.; Tsai, H. L.; Chau, L. Y. J. Biol. Chem. 2003, 278, 19325.
[92] Nguyen, D.; Nguyen, T. K.; Rice, S. A.; Boyer, C. Biomacromolecules 2015, 16, 2776.
[93] Motterlini, R.; Mann, B. E.; Foresti, R. Expert Opin. Investig. Drugs 2005, 14, 1305.
[94] Mann, B. E. Medicinal Organometallic Chemistry. Topics in Organometallic Chemistry, Eds.:Jaouen, G.; Metzler-Nolte, N., Berlin, Heidelberg, Springer, 2010, Vol. 32, p. 247.
[95] Ferrandiz, M. L.; Maicas, N.; Garcia-Arnandis, I.; Terencio, M. C.; Motterlini, R.; Devesa, I.; Joosten, L. A.; van den Berg, W. B.; Alcaraz, M. J. Ann. Rheum. Dis. 2008, 67, 1211.
[96] Bathoorn, E.; Slebos, D. J.; Postma, D. S.; Koeter, G. H.; van Oosterhout, A. J.; van der Toorn, M.; Boezen, H. M.; Kerstjens, H. A. Eur. Respir. J. 2007, 30, 1131.
[97] Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654.
[98] Morse, D.; Pischke, S. E.; Zhou, Z.; Davis, R. J.; Flavell, R. A.; Loop, T.; Otterbein, S. L.; Otterbein, L. E.; Choi, A. M. J. Biol. Chem. 2003, 278, 36993.
[99] Otterbein, L. E.; Choi, A. M. Am. J. Physiol. Lung Cell Mol. Physiol. 2000, 279, L1029.
[100] Pae, H. O.; Oh, G. S.; Choi, B. M.; Chae, S. C.; Kim, Y. M.; Chung, K. R.; Chung, H. T. J. Immunol. 2004, 172, 4744.
[101] Song, R. P.; Zhou, Z. H.; Kim, P. K.; Shapiro, R. A.; Liu, F.; Ferran, C.; Choi, A. M.; Otterbein, L. E. J. Biol. Chem. 2004, 279, 44327.
[102] Bani-Hani, M. G.; Greenstein, D.; Mann, B. E.; Green, C. J.; Motterlini, R. J. Pharmacol. Exp. Ther. 2006, 318, 1315.
[103] Bani-Hani, K. E.; Bani-Hani, B. K. World J. Gastroenterol. 2006, 12, 1521.
[104] Guillen, M. I.; Megias, J.; Clerigues, V.; Gomar, F.; Alcaraz, M. J. Rheumatol. 2008, 47, 1323.
[105] Hasegawa, U.; van der Vlies, A. J.; Simeoni, E.; Wandrey, C.; Hubbell, J. A. J. Am. Chem. Soc. 2010, 132, 18273.
[106] Van der Vlies, A. J.; Inubushi, R.; Uyama, H.; Hasegawa, U. Bioconjug. Chem. 2016, 27, 1500.
[107] Qureshi, O. S.; Zeb, A.; Akram, M.; Kim, M. S.; Kang, J. H.; Kim, H. S.; Majid, A.; Han, I.; Chang, S. Y.; Bae, O. N.; Kim, J. K. Eur. J. Pharm. Biopharm. 2016, 108, 187.
[108] Fujita, K.; Tanaka, Y.; Sho, T.; Ozeki, S.; Abe, S.; Hikage, T.; Kuchimaru, T.; Kizaka-Kondoh, S.; Ueno, T. J. Am. Chem. Soc. 2014, 136, 16902.
[109] Fujita, K.; Tanaka, Y.; Abe, F.; Ueno, T. Angew. Chem., Int. Ed. 2016, 55, 1056.
[110] Nobre, L. S.; Seixas, J. D.; Romao, C. C.; Saraiva, L. M. Antimicrob. Agents Chemother. 2007, 51, 4303.
[111] Lu, Y.; Slomberg, D. L.; Schoenfisch, M. H. Biomaterials 2014, 35, 1716.
[112] Lu, Y.; Slomberg, D. L.; Shah, A.; Schoenfisch, M. H. Biomacromolecules 2013, 14, 3589.
[113] Murray, T. S.; Okegbe, C.; Gao, Y.; Kazmierczak, B. I.; Motterlini, R.; Dietrich, L. E.; Bruscia, E. M. PLoS One 2012, 7, e35499.
[114] Nobre, L. S.; Al-Shahrour, F.; Dopazo, J.; Saraiva, L. M. Microbiology 2009, 155, 813.
[115] Desmard, M.; Davidge, K. S.; Bouvet, O.; Morin, D.; Roux, D.; Foresti, R.; Ricard, J. D.; Denamur, E.; Poole, R. K.; Montravers, P.; Motterlini, R.; Boczkowski, J. FASEB J. 2009, 23, 1023.
[116] Loboda, A.; Jazwa, A.; Wegiel, B.; Jozkowicz, A.; Dulak, J. Cell Mol. Biol. (Noisy-le-grand) 2005, 51, 347.
[117] Chung, S. W.; Liu, X. L.; Macias, A. A.; Baron, R. M.; Perrella, M. A. J. Clin. Invest. 2008, 118, 239.
[118] Bang, C. S.; Kruse, R.; Johansson, K.; Persson, K. BMC Microbiology 2016, 16, 64.
[119] Flanagan, L.; Steen, R. R.; Saxby, K.; Klatter, M.; Aucott, B. J.; Winstanley, C.; Fairlamb, I. J. S.; Lynam, J. M.; Parkin, A.; Friman, V.-P. Front. Microbiol. 2018, 9, 195.
[120] Wilson, J. L.; Jesse, H. E.; Poole, R. K.; Davidge, K. S. Curr. Pharm. Biotechnol. 2012, 13, 760.
[121] Li, B.; Zhang, X. Y.; Yang, J. Z.; Zhang, Y. J.; Li, W. X.; Fan, C. H.; Huang, Q. Int. J. Nanomed. 2014, 9, 4697.
[122] Folkman, J. N. Engl. J. Med. 1971, 285, 1182.
[123] Calderon-Montano, J. M.; Burgos-Moron, E.; Orta, M. L.; Mateos, S.; Lopez-Lazaro, M. Planta Med. 2013, 79, 1017.
[124] Pompella, A.; Visvikis, A.; Paolicchi, A.; De Tata, V.; Casini, A. F. Biochem. Pharmacol. 2003, 66, 1499.
[125] Wu, X. Y.; Zhang, L.; Lü, D.; Liu, Y. H.; Chen, Y. N.; Su, W. J.; Luo, N.; Xiang, R. Acta Chim. Sinica 2013, 71, 299. (吴星怡, 张磊, 吕丹, 刘艳华, 陈亚南, 苏位君, 罗娜, 向荣, 化学学报, 2013, 71, 299.)
[126] Matsumura, Y.; Maeda, H. Cancer Res. 1986, 46, 6387.
[127] Zheng, D. W.; Li, B.; Li, C. X.; Xu, L.; Fan, J. X.; Lei, Q.; Zhang, X. Z. Adv. Mater. 2017, 29, 1703822.
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