Progress of Porphyrin-based Nanoassemblies for Cancer Theranostics

doi:10.1007/s40242-023-3127-9

Abstract

Abstract: Porphyrins are indispensable in almost all forms of life. As photosensitizers, porphyrins have excellent imaging, photodynamic, photothermal, chemotherapeutic, and enzymatic properties, and play vital roles in biological diagnosis and therapy. However, the hydrophobicity of porphyrin molecules and the poor therapeutic effect of a single component on complex tumor systems hinder the applications of porphyrin monomers. Porphyrin assemblies could solve the problem of hydrophilicity and have good biocompatibility. First, this review briefly introduces the porphyrin self-assembly method, and the co-assembly of porphyrin and porphyrin, porphyrin and polymer, porphyrin and polypeptide, porphyrin and inorganic nanocrystals. The synergistic effect of co-assembly could solve the hydrophilia problem and achieve the enhanced functionalization. Then, the widened red shift of the spectrum, the increased yield, the increased drug loading, and the increased singlet oxygen yields are discussed. The research progresses of porphyrin-based assemblies in the direction of biological diagnosis and treatment are also reviewed. Finally, future perspectives and potential future research on the challenges are addressed.

Key words: Porphyrin, Supramolecular interaction, Self-assembly, Nanoassembly, Cancer, Imaging, Theranostics

WANG Mengyue, HUANG Guan, YOU Zhongqi, JIA Rixin, ZHONG Yong, BAI Feng. Progress of Porphyrin-based Nanoassemblies for Cancer Theranostics[J]. Chemical Research in Chinese Universities, 2023, 39(4): 612-623.

References

[1] Wang Y., Gong N., Li Y., Lu Q., Wang X., Li J., J. Am. Chem. Soc., 2020, 142, 1735
[2] Guo B., Huang Z., Shi Q., Middha E., Xu S., Li L., Wu M., Jiang J., Hu Q., Fu Z., Liu B., Adv. Funct. Mater., 2019, 30, 1907093
[3] Chang K., Liu Y., Hu D., Qi Q., Gao D., Wang Y., Li D., Zhang X., Zheng H., Sheng Z., Yuan Z., ACS Appl. Mater. Interfaces, 2018, 10, 7012
[4] Jiang M., Kwok R. T. K., Li X., Gui C., Lam J. W. Y., Qu J., Tang B. Z., J. Mater. Chem. B, 2018, 6, 2557
[5] Cunningham D., Allum W. H., Stenning S. P., Thompson J. N., van de Velde C. J., Nicolson M., Scarffe J. H., Lofts F. J., Falk S. J., Iveson T. J., Smith D. B., Langley R, E., Verma M., Weeden S., Chua Y J., N. Engl. J. Med., 2006, 355, 11
[6] Moore H. C. F., Unger J. M., Phillips K.-A., Boyle F., Hitre E., Porter D., Francis P. A., Goldstein L. J., Gomez H. L., Vallejos C. S., Partridge A. H., Dakhil S. R., Garcia A. A., Gralow J., Lombard J. M., Forbes J. F., Martino S., Barlow W. E., Fabian C. J., Minasian L., Meyskens F. L., Gelber R. D., Hortobagyi G. N., Albain K. S., N. Engl. J. Med., 2015, 372, 923
[7] Wang P., Fan Y., Lu L., Liu L., Fan L., Zhao M., Xie Y., Xu C., Zhang F., Nat. Commun., 2018, 9, 2898
[8] Hamdy F. C., Donovan J. L., Lane J. A., Mason M., Metcalfe C., Holding P., Davis M., Peters T. J., Turner E. L., Martin R. M., Oxley J., Robinson M., Staffurth J., Walsh E., Bollina P., Catto J., Doble A., Doherty A., Gillatt D., Kockelbergh R., Kynaston H., Paul A., Powell P., Prescott S., Rosario D. J., Rowe E., Neal D. E., Protec T. S. G., N. Engl. J. Med., 2016, 375, 1415
[9] Romond E. H., Perez E. A., Bryant J., Suman V. J., Geyer C. E., Davidson N. E., Tan-Chiu E., Martino S., Paik S., Kaufman P. A., Swain S. M., Pisansky T. M., Fehrenbacher L., Kutteh L. A., Vogel V. G., Visscher D. W., Yothers G., Jenkins R. B., Brown A. M., Dakhil S. R., Mamounas E. P., Lingle W. L., Klein P. M., Ingle J. N., Wolmark N., N. Engl. J. Med., 2005, 353, 1673
[10] Dai J., Cheng Y., Wu J., Wang Q., Wang W., Yang J., Zhao Z., Lou X., Xia F., Wang S., Tang B. Z., ACS Nano, 2020, 14, 14698
[11] Chen Q., Liang C., Wang X., He J., Li Y., Liu Z., Biomaterials, 2014, 35, 9355
[12] Wang X., Ramamurthy G., Shirke A. A., Walker E., Mangadlao J., Wang Z., Wang Y., Shan L., Schluchter M. D., Dong Z., Brady-Kalnay S. M., Walker N. K., Gargesha M., MacLennan G., Luo D., Sun R., Scott B., Roy D., Li J., Basilion J. P., Cancer Res., 2020, 80, 156
[13] Debie P., Devoogdt N., Hernot S., Antibodies(Basel), 2019, 8, 12
[14] Cheng L., Jiang D., Kamkaew A., Valdovinos H. F., Im H. J., Feng L., England C. G., Goel S., Barnhart T. E., Liu Z., Cai W., Adv. Funct. Mater., 2017, 27, 1702928
[15] Li S. Y., Cheng H., Qiu W. X., Zhang L., Wan S. S., Zeng J. Y., Zhang X. Z., Biomaterials, 2017, 142, 149
[16] Chen W. H., Luo G. F., Qiu W. X., Lei Q., Liu L. H., Wang S. B., Zhang X. Z., Biomaterials, 2017, 117, 54
[17] Shao S., Rajendiran V., Lovell J. F., Coord. Chem. Rev., 2019, 379, 99
[18] Zhao H., Zang L., Zhao H., Qin F., Li Z., Zhang Z., Cao W., J. Phys. Chem. C, 2015, 119, 10558
[19] Rajora M. A., Lou J. W. H., Zheng G., Chem. Soc. Rev., 2017, 46, 6433
[20] Chen W., Zhao J., Hou M., Yang M., Yi C., Nanoscale, 2021, 13, 16197
[21] Zou T., Lum C. T., Lok C. N., Zhang J. J., Che C. M., Chem. Soc. Rev., 2015, 44, 8786
[22] Wang X., Wang J., Wang J., Zhong Y., Han L., Yan J., Duan P., Shi B., Bai F., Nano Lett., 2021, 21, 3418
[23] Wang D., Niu L., Qiao Z. Y., Cheng D. B., Wang J., Zhong Y., Bai F., Wang H., Fan H., ACS Nano, 2018, 12, 3796
[24] Ethirajan M., Chen Y., Joshi P., Pandey R. K., Chem. Soc. Rev., 2011, 40, 340
[25] Kou J., Dou D., Yang L., Oncotarget, 2017, 8, 81591
[26] Xue X., Lindstrom A., Li Y., Bioconjug. Chem., 2019, 30, 1585
[27] Park J., Jiang Q., Feng D., Mao L., Zhou H. C., J. Am. Chem. Soc., 2016, 138, 3518
[28] Min H., Wang J., Qi Y., Zhang Y., Han X., Xu Y., Xu J., Li Y., Chen L., Cheng K., Liu G., Yang N., Li Y., Nie G., Adv. Mater., 2019, 31, e1808200
[29] Cai J.-Q., Liu X.-M., Gao Z.-J., Li L.-L., Wang H., Mater. Today, 2021, 45, 77
[30] Tian J., Zhang W., Prog. Polym. Sci., 2019, 95, 65
[31] Zhao L., Qu R., Li A., Ma R., Shi L., Chem. Commun., 2016, 52, 13543
[32] Fan H., Yang K., Boye D. M., Sigmon T., Malloy K. J., Xu H., Lopez G. P., Brinker C. J., Science, 2004, 304, 567
[33] Wang Z., Medforth C. J., Shelnutt J. A., J. Am. Chem. Soc., 2004, 126, 15954
[34] Liu K., Xing R., Zou Q., Ma G., Mohwald H., Yan X., Angew. Chem. Int. Ed., 2016, 55, 3036
[35] Zhang X., Gong C., Akakuru O. U., Su Z., Wu A., Wei G., Chem. Soc. Rev., 2019, 48, 5564
[36] Grzelczak M., Liz-Marzan L. M., Klajn R., Chem. Soc. Rev., 2019, 48, 1342
[37] Abbas M., Zou Q., Li S., Yan X., Adv. Mater., 2017, 29, 1605021
[38] Liu Y., Wang L., Feng H., Ren X., Ji J., Bai F., Fan H., Nano Lett., 2019, 19, 2614
[39] Tian T., Bao J., Wang J., Wang J., Ge Y., Li Z., Gao S., You Z., Yang X., Zhong Y., Bai F., Nano Res., 2022, 15, 9114
[40] Wang J., Gao S., Wang X., Zhang H., Ren X., Liu J., Bai F., Nano Res., 2021, 15, 2347
[41] Zhao Y., Hu Y., Zhong Y., Wang J., Liu Z., Bai F., Zhang D., J. Phys. Chem. C, 2021, 125, 22318
[42] Bai F., Sun Z., Wu H., Haddad R. E., Coker E. N., Huang J. Y., Rodriguez M. A., Fan H., Nano Lett., 2011, 11, 5196
[43] Wang J., Zhong Y., Wang X., Yang W., Bai F., Zhang B., Alarid L., Bian K., Fan H., Nano Lett., 2017, 17, 6916
[44] Wang J., Zhong Y., Wang L., Zhang N., Cao R., Bian K., Alarid L., Haddad R. E., Bai F., Fan H., Nano Lett., 2016, 16, 6523
[45] Zhong Y., Wang J., Zhang R., Wei W., Wang H., Lu X., Bai F., Wu H., Haddad R., Fan H., Nano Lett., 2014, 14, 7175
[46] Cao R., Wang G., Ren X., Duan P. C., Wang L., Li Y., Chen X., Zhu R., Jia Y., Bai F., Nano Lett., 2022, 22, 157
[47] Cao R., Wang J., Li Y., Sun J., Bai F., Nano Res., 2022, 15, 5719
[48] Chen J., Chen F., Zhang L., Yang Z., Deng T., Zhao Y., Zheng T., Gan X., Zhong H., Geng Y., Fu X., Wang Y., Yu C., ACS Appl. Mater. Interfaces, 2021, 13, 27856
[49] Sun D., Zhang Z., Chen M., Zhang Y., Amagat J., Kang S., Zheng Y., Hu B., Chen M., ACS Appl. Mater. Interfaces, 2020, 12, 40728
[50] Amdursky N., Wang X., Meredith P., Riley D. J., Payne D. J., Bradley D. D. C., Stevens M. M., Adv. Mater., 2017, 29, 1700810
[51] Wang K., Chen J., Lin L., Yan N., Yang W., Cai K., Tian H., Chen X., Nano Today, 2022, 46, 101579
[52] Zhang Z., Shi Y., Pan Y., Cheng X., Zhang L., Chen J., Li M. J., Yi C., J. Mater. Chem. B, 2014, 2, 5020
[53] Shi Y., Zhang H., Yue Z., Zhang Z., Teng K. S., Li M. J., Yi C., Yang M., Nanotechnology, 2013, 24, 375501
[54] Rastogi S. K., Pal P., Aston D. E., Bitterwolf T. E., Branen A. L., ACS Appl. Mater. Interfaces, 2011, 3, 1731
[55] Pal P., Rastogi S. K., Gibson C. M., Aston D. E., Branen A. L., Bitterwolf T. E., ACS Appl. Mater. Interfaces, 2011, 3, 279
[56] Feng L., Zhu C., Yuan H., Liu L., Lv F., Wang S., Chem. Soc. Rev., 2013, 42, 6620
[57] Shi Y., Chen Z., Cheng X., Pan Y., Zhang H., Zhang Z., Li C. W., Yi C., Biosens. Bioelectron., 2014, 61, 397
[58] Hou M., Chen W., Zhao J., Dai D., Yang M., Yi C., Chin. Chem. Lett., 2022, 33, 4101
[59] Su S., Ding Y., Li Y., Wu Y., Nie G., Biomaterials, 2016, 80, 169
[60] Yu B., Wei H., He Q., Ferreira C. A., Kutyreff C. J., Ni D., Rosenkrans Z. T., Cheng L., Yu F., Engle J. W., Lan X., Cai W., Angew. Chem. Int. Ed., 2018, 57, 218
[61] Chen W., Wang Q., Ma J., Li C. W., Yang M., Yi C., Mikrochim. Acta, 2018, 185, 523
[62] Wang J., Hu Y., Wang X., Gao S., Zhong Y., Liu J., Bai F., ACS Appl. Bio. Mater., 2021, 4, 7322
[63] Hambley T. W., Hait W. N., Cancer Res., 2009, 69, 1259
[64] Guleria M., Suman S. K., Kumar N., Sharma A. K., Amirdhanayagam J., Sarma H. D., Satpati D., Das T., RSC Med. Chem., 2022, 13, 1378
[65] Wu Y., Chau H. F., Yeung Y. H., Thor W., Kai H. Y., Chan W. L., Wong K. L., Angew. Chem. Int. Ed., 2022, 61, e202207532
[66] Chen J. X., Wang H. Y., Li C., Han K., Zhang X. Z., Zhuo R. X., Biomate-rials, 2011, 32, 1678
[67] Wijerathne N. K., Kumar M., Ulijn R. V., Chemistry, 2019, 25, 11847
[68] Zhao L., Ren X., Yan X., CCS Chemistry, 2021, 3, 678
[69] Zhao L., Li S., Liu Y., Xing R., Yan X., CCS Chemistry, 2019, 1, 173
[70] Cui L., Tokarz D., Cisek R., Ng K. K., Wang F., Chen J., Barzda V., Zheng G., Angew. Chem. Int. Ed., 2015, 54, 13928
[71] Xia R., Zheng X., Hu X., Liu S., Xie Z., ACS Appl. Mater. Interfaces, 2019, 11, 5782
[72] Li Y., Chu J., Wang D., Zhu L., Kong D., Mater. Chem. Front., 2021, 5, 3139
[73] Wu Q., Xia R., Li C., Li Y., Sun T., Xie Z., Jing X., Mater. Chem. Front., 2021, 5, 8333
[74] Wang J., Wang Z., Zhong Y., Zou Y., Wang C., Wu H., Lee A., Yang W., Wang X., Liu Y., Zhang D., Yan J., Hao M., Zheng M., Chung R., Bai F., Shi B., Biomaterials, 2020, 229, 119576
[75] Wang X., Yan F., Liu X., Wang P., Shao S., Sun Y., Sheng Z., Liu Q., Lovell J. F., Zheng H., J. Control Release, 2018, 286, 358
[76] Tang M., Song Y., Lu Y. L., Zhang Y. M., Yu Z., Xu X., Liu Y., J. Med. Chem., 2022, 65, 6764
[77] Zheng N., Zhang Z., Kuang J., Wang C., Zheng Y., Lu Q., Bai Y., Li Y., Wang A., Song W., ACS Appl. Mater. Interfaces, 2019, 11, 18224
[78] Liu X., Zhan W., Gao G., Jiang Q., Zhang X., Zhang H., Sun X., Han W., Wu F. G., Liang G., J. Am. Chem. Soc., 2023, 145, 7918
[79] Jiao J., He J., Li M., Yang J., Yang H., Wang X., Yang S., Nanoscale, 2022, 14, 6373
[80] Cai Q., Fei Y., An H. W., Zhao X. X., Ma Y., Cong Y., Hu L., Li L. L., Wang H., ACS Appl. Mater. Interfaces, 2018, 10, 9197
[81] Wang D., Cheng D. B., Ji L., Niu L. J., Zhang X. H., Cong Y., Cao R. H., Zhou L., Bai F., Qiao Z. Y., Wang H., Biomaterials, 2021, 264, 120386
[82] Sun Y., Zhang Y., Gao Y., Wang P., He G., Blum N., Lin J., Liu Q., Wang X., Huang P., Adv. Mater., 2022, 34, e2209394
[83] Xiong H., Zhou K., Yan Y., Miller J. B., Siegwart D. J., ACS Appl. Mater. Interfaces, 2018, 10, 16335
[84] Li Z., Li S., Guo Y., Yuan C., Yan X., Schanze K. S., ACS Nano, 2021, 15, 4979
[85] Zhao L. P., Zheng R. R., Chen H. Q., Liu L. S., Zhao X. Y., Liu H. H., Qiu X. Z., Yu X. Y., Cheng H., Li S. Y., Nano Lett., 2020, 20, 2062
[86] Li X. Y., Deng F. A., Zheng R. R., Liu L. S., Liu Y. B., Kong R. J., Chen A. L., Yu X. Y., Li S. Y., Cheng H., Small, 2021, 17, e2102470
[87] Tao D., Feng L., Chao Y., Liang C., Song X., Wang H., Yang K., Liu Z., Adv. Funct. Mater., 2018, 28, 1804901
[88] Guo B., Feng G., Manghnani P. N., Cai X., Liu J., Wu W., Xu S., Cheng X., Teh C., Liu B., Small, 2016, 12, 6243
[89] Li C., Luo Z., Yang L., Chen J., Cheng K., Xue Y., Liu G., Luo X., Wu F., Mater Today Bio., 2022, 13, 100198
[90] Mitragotri S., Nat. Rev. Drug Discov., 2005, 4, 255
[91] Jadvar H., Colletti P. M., Eur. J. Radiol., 2014, 83, 84
[92] Chen M., Liang X., Dai Z., Nanoscale, 2019, 11, 10178
[93] Lv Z., Zou L., Wei H., Liu S., Huang W., Zhao Q., ACS Appl. Mater. Interfaces, 2018, 10, 19523
[94] Fan W., Yung B., Huang P., Chen X., Chem. Rev., 2017, 117, 13566
[95] Shi Y., Liu S., Liu Y., Sun C., Chang M., Zhao X., Hu C., Pang M., ACS Appl. Mater. Interfaces, 2019, 11, 12321
[96] Wu B., Li X. Q., Huang T., Lu S. T., Wan B., Liao R. F., Li Y. S., Baidya A., Long Q. Y., Xu H. B., Biomater. Sci., 2017, 5, 1746