Abstract
Due to the formation of dynamic boronate ester bonds between phenylboronic acid (PBA) and 1,2- and 1,3-diols, PBA-containing biomaterials show increasing applications in biomedical areas, including responsive nanobiomaterials for targeting delivery of chemical drugs, protein drugs, gene drugs and imaging agents in vitro and in vivo for detection of various bioactive molecules such as sialic acid, saccharides, adenosine triphosphate (ATP) and dopamine. With the specific reaction between PBA and sialic acid, which is overexpressed in many kinds of cancer cells, PBA has been used as a targeting moiety for tumor-targeting drug delivery. Additionally, PBA as an electron acceptor affords nanomaterials Lewis acid-base coordination with electron donor atoms such as nitrogen and oxygen, which can be exploited for developing drug delivery systems with high drug loading. Furthermore, PBA-containing materials can stoichiometric consume reactive oxygen species (ROS) and show a nucleus targeting ability. This current review outlined PBA-containing biomaterials with various responsive abilities including sialic acid-targeting, sugars-binding, ROS-response, ATP-response, dopamine-binding, and nuclear targeting. On this basis, their biomedical applications were summarized.
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Brooks WLA, Sumerlin BS. Chem Rev, 2016, 1: 1375–1397
Guo Z, Shin I, Yoon J. Chem Commun, 2012, 1: 5956–5967
Ghebregzabher M, Rufini S, Sapia GM, Lato M. J Chromatogr A, 1979, 1: 1–16
Büll C, Stoel MA, den Brok MH, Adema GJ. Cancer Res, 2014, 1: 3199–3204
Gorrini C, Harris IS, Mak TW. Nat Rev Drug Discov, 2013, 1: 931–947
Di Virgilio F, Sarti AC, Falzoni S, De Marchi E, Adinolfi E. Nat Rev Cancer, 2018, 1: 601–618
Berke JD. Nat Neurosci, 2018, 1: 787–793
Wang J, Wu W, Jiang X. Nanomedicine, 2015, 1: 1149–1163
Jiang XC, Xiang JJ, Wu HH, Zhang TY, Zhang DP, Xu QH, Huang XL, Kong XL, Sun JH, Hu YL, Li K, Tabata Y, Shen YQ, Gao JQ. Adv Mater, 2019, 31: 1807591
Sun X, Xu Q, Kim G, Flower SE, Lowe JP, Yoon J, Fossey JS, Qian X, Bull SD, James TD. Chem Sci, 2014, 1: 3368–3373
Zhao L, Xiao C, Wang L, Gai G, Ding J. Chem Commun, 2016, 1: 7633–7652
Ma R, Shi L. Polym Chem, 2014, 1: 1503–1518
Guan Y, Zhang Y. Chem Soc Rev, 2013, 1: 8106–8121
Shinde S, El-Schich Z, Malakpour A, Wan W, Dizeyi N, Mohammadi R, Rurack K, Gjörloff Wingren A, Sellergren B. J Am Chem Soc, 2015, 1: 13908–13912
Kim J, Lee YM, Kim H, Park D, Kim J, Kim WJ. Biomaterials, 2016, 1: 102–111
Naito M, Ishii T, Matsumoto A, Miyata K, Miyahara Y, Kataoka K. Angew Chem Int Ed, 2012, 1: 10751–10755
Yan J, Springsteen G, Deeter S, Wang B. Tetrahedron, 2004, 1: 11205–11209
Ellis GA, Palte MJ, Raines RT. J Am Chem Soc, 2012, 1: 3631–3634
Adamczyk B, Tharmalingam T, Rudd PM. Biochim Biophys Acta, 2012, 1820: 1347–1353
Pearce OMT, Läubli H. Glycobiology, 2015, 1: 111–128
Whited J, Zhang X, Nie H, Wang D, Li Y, Sun XL. ACS Chem Biol, 2018, 1: 2364–2374
Christiansen MN, Chik J, Lee L, Anugraham M, Abrahams JL, Packer NH. Proteomics, 2014, 1: 525–546
Otsuka H, Uchimura E, Koshino H, Okano T, Kataoka K. J Am Chem Soc, 2003, 1: 3493–3502
Lei L, Xu Z, Hu X, Lai Y, Xu J, Hou B, Wang Y, Yu H, Tian Y, Zhang W. Small, 2019, 15: 1900157
Liu M, Tang X, Ding J, Liu M, Zhao B, Deng Y, Song Y. Pharm Res, 2019, 36: 176
Lee JY, Chung SJ, Cho HJ, Kim DD. Adv Funct Mater, 2015, 1: 3705–3717
Wang X, Zhen X, Wang J, Zhang J, Wu W, Jiang X. Biomaterials, 2013, 1: 4667–4679
Wang J, Wu W, Zhang Y, Wang X, Qian H, Liu B, Jiang X. Biomaterials, 2014, 1: 866–878
Wang X, Tang H, Wang C, Zhang J, Wu W, Jiang X. Theranostics, 2016, 1: 1378–1392
Chen W, Ji S, Qian X, Zhang Y, Li C, Wu W, Wang F, Jiang X. Polym Chem, 2017, 1: 2105–2114
Zhang Y, Chen W, Yang C, Fan Q, Wu W, Jiang X. J Control Release, 2016, 1: 115–124
Qian X, Ge L, Yuan K, Li C, Zhen X, Cai W, Cheng R, Jiang X. Theranostics, 2019, 1: 7417–7430
Liu S, Pan J, Liu J, Ma Y, Qiu F, Mei L, Zeng X, Pan G. Small, 2018, 14: 1703968
Obuobi S, Voo ZX, Low MW, Czarny B, Selvarajan V, Ibrahim NL, Yang YY, Ee PLR. Adv Healthc Mater, 2018, 7: 1701388
Long Y, Lu Z, Mei L, Li M, Ren K, Wang X, Tang J, Zhang Z, He Q. Adv Sci, 2018, 5: 1800229
Cao J, Gao X, Cheng M, Niu X, Li X, Zhang Y, Liu Y, Wang W, Yuan Z. Nano Lett, 2019, 1: 1665–1674
Zheng C, Wang Q, Wang Y, Zhao X, Gao K, Liu Q, Zhao Y, Zhang Z, Zheng Y, Cao J, Chen H, Shi L, Kang C, Liu Y, Lu Y. Adv Mater, 2019, 31: 1902542
Matsumoto A, Sato N, Kataoka K, Miyahara Y. J Am Chem Soc, 2009, 1: 12022–12023
Matsumoto A, Cabral H, Sato N, Kataoka K, Miyahara Y. Angew Chem Int Ed, 2010, 1: 5494–5497
Cheng L, Zhang X, Zhang Z, Chen H, Zhang S, Kong J. Talanta, 2013, 1: 823–829
Qian R, Ding L, Yan L, Ju H. Anal Chim Acta, 2015, 1: 85–90
Liu HW, Law WHT, Lee LCC, Lau JCW, Lo KKW. Chem Asian J, 2017, 1: 1545–1556
Frullano L, Rohovec J, Aime S, Maschmeyer T, Prata MI, de Lima JJP, Geraldes CFGC, Peters JA. Chem Eur J, 2004, 1: 5205–5217
Tsoukalas C, Geninatti-Crich S, Gaitanis A, Tsotakos T, Paravatou-Petsotas M, Aime S, Jiménez-Juárez R, Anagnostopoulos CD, Djanashvili K, Bouziotis P. Mol Imag Biol, 2018, 1: 798–807
Geninatti Crich S, Alberti D, Szabo I, Aime S, Djanashvili K. Angew Chem Int Ed, 2013, 1: 1161–1164
Bie Z, Chen Y, Ye J, Wang S, Liu Z. Angew Chem Int Ed, 2015, 1: 10211–10215
Ye J, Chen Y, Liu Z. Angew Chem Int Ed, 2014, 1: 10386–10389
Di H, Liu H, Li M, Li J, Liu D. Anal Chem, 2017, 1: 5874–5881
Yin D, Wang S, He Y, Liu J, Zhou M, Ouyang J, Liu B, Chen HY, Liu Z. Chem Commun, 2015, 1: 17696–17699
Wang S, Yin D, Wang W, Shen X, Zhu JJ, Chen HY, Liu Z. Sci Rep, 2016, 6: 22757
Liu R, Cui Q, Wang C, Wang X, Yang Y, Li L. ACS Appl Mater Interfaces, 2017, 1: 3006–3015
Li H, Lee CH, Shin I. Org Lett, 2019, 1: 4628–4631
Zaykov AN, Mayer JP, DiMarchi RD. Nat Rev Drug Discov, 2016, 1: 425–439
Paszek MJ, DuFort CC, Rossier O, Bainer R, Mouw JK, Godula K, Hudak JE, Lakins JN, Wijekoon AC, Cassereau L, Rubashkin MG, Magbanua MJ, Thorn KS, Davidson MW, Rugo HS, Park JW, Hammer DA, Giannone G, Bertozzi CR, Weaver VM. Nature, 2014, 1: 319–325
Tarbell JM, Cancel LM. J Intern Med, 2016, 1: 97–113
Wang J, Wang Z, Yu J, Kahkoska AR, Buse JB, Gu Z. Adv Mater, 2019, 1902004
Hou L, Zheng Y, Wang Y, Hu Y, Shi J, Liu Q, Zhang H, Zhang Z. ACS Appl Mater Interfaces, 2018, 1: 21927–21938
Xiao Y, Hu Y, Du J. Mater Horiz, 2019, 1: 2047–2055
Li C, Huang F, Liu Y, Lv J, Wu G, Liu Y, Ma R, An Y, Shi L. Langmuir, 2018, 1: 12116–12125
Chou DHC, Webber MJ, Tang BC, Lin AB, Thapa LS, Deng D, Truong JV, Cortinas AB, Langer R, Anderson DG. Proc Natl Acad Sci USA, 2015, 1: 2401–2406
Yu J, Qian C, Zhang Y, Cui Z, Zhu Y, Shen Q, Ligler FS, Buse JB, Gu Z. Nano Lett, 2017, 1: 733–739
Hu X, Yu J, Qian C, Lu Y, Kahkoska AR, Xie Z, Jing X, Buse JB, Gu Z. ACS Nano, 2017, 1: 613–620
Chen Z, Wang J, Sun W, Archibong E, Kahkoska AR, Zhang X, Lu Y, Ligler FS, Buse JB, Gu Z. Nat Chem Biol, 2018, 1: 86–93
Wang J, Yu J, Zhang Y, Kahkoska AR, Wang Z, Fang J, Whitelegge JP, Li S, Buse JB, Gu Z. Proc Natl Acad Sci USA, 2019, 1: 10744–10748
Yu J, Zhang Y, Wang J, Wen D, Kahkoska AR, Buse JB, Gu Z. Nano Res, 2019, 1: 1539–1545
Wang J, Yu J, Zhang Y, Zhang X, Kahkoska AR, Chen G, Wang Z, Sun W, Cai L, Chen Z, Qian C, Shen Q, Khademhosseini A, Buse JB, Gu Z. Sci Adv, 2019, 5: eaaw4357
Jin X, Zhu DD, Chen BZ, Ashfaq M, Guo XD. Adv Drug Deliver Rev, 2018, 1: 119–137
Wang J, Ye Y, Yu J, Kahkoska AR, Zhang X, Wang C, Sun W, Corder RD, Chen Z, Khan SA, Buse JB, Gu Z. ACS Nano, 2018, 1: 2466–2473
Chen S, Matsumoto H, Moro-oka Y, Tanaka M, Miyahara Y, Suganami T, Matsumoto A. ACS Biomater Sci Eng, 2019, 1: 5781–5789
Matsumoto A, Tanaka M, Matsumoto H, Ochi K, Moro-Oka Y, Kuwata H, Yamada H, Shirakawa I, Miyazawa T, Ishii H, Kataoka K, Ogawa Y, Miyahara Y, Suganami T. Sci Adv, 2017, 3: eaaq0723
Dong Y, Lu X, Wang P, Liu W, Zhang S, Wu Z, Chen H. J Mater Chem B, 2018, 1: 6744–6751
Shen MY, Chen JF, Luo CH, Lee S, Li CH, Yang YL, Tsai YH, Ho BC, Bao LR, Lee TJ, Jan YJ, Zhu YZ, Cheng S, Feng FY, Chen P, Hou S, Agopian V, Hsiao YS, Tseng HR, Posadas EM, Yu HH. Adv Healthc Mater, 2018, 7: 1700701
Liu L, Tian X, Ma Y, Duan Y, Zhao X, Pan G. Angew Chem Int Ed, 2018, 1: 7878–7882
Pan G, Guo B, Ma Y, Cui W, He F, Li B, Yang H, Shea KJ. J Am Chem Soc, 2014, 1: 6203–6206
Liu H, Li Y, Sun K, Fan J, Zhang P, Meng J, Wang S, Jiang L. J Am Chem Soc, 2013, 1: 7603–7609
Zhan W, Qu Y, Wei T, Hu C, Pan Y, Yu Q, Chen H. ACS Appl Mater Interfaces, 2018, 1: 10647–10655
Pan X, Chen Y, Zhao P, Li D, Liu Z. Angew Chem Int Ed, 2015, 1: 6173–6176
Hashimoto T, Kumai M, Maeda M, Miyoshi K, Tsuchido Y, Fujiwara S, Hayashita T. Front Chem Sci Eng, 2020, 1: 53–60
Pan Y, Yang M, Zhang M, Jia M. Sens Actuat B-Chem, 2019, 1: 48–54
Ma D, Wu X, Wang Y, Liao H, Wan P, Zhang L. ACS Appl Mater Interfaces, 2019, 1: 41701–41709
Bao C, Guo Z, Sun H, Sun J. ACS Appl Mater Interfaces, 2019, 1: 9478–9486
Yesilyurt V, Webber MJ, Appel EA, Godwin C, Langer R, Anderson DG. Adv Mater, 2016, 1: 86–91
Zhi X, Zheng C, Xiong J, Li J, Zhao C, Shi L, Zhang Z. Langmuir, 2018, 1: 12914–12923
Dong Y, Wang W, Veiseh O, Appel EA, Xue K, Webber MJ, Tang BC, Yang XW, Weir GC, Langer R, Anderson DG. Langmuir, 2016, 1: 8743–8747
Li Y, Yang L, Zeng Y, Wu Y, Wei Y, Tao L. Chem Mater, 2019, 1: 5576–5583
Bao C, Jiang YJ, Zhang H, Lu X, Sun J. Adv Funct Mater, 2018, 28: 1800560
Nishiyabu R, Kubo Y, James TD, Fossey JS. Chem Commun, 2011, 1: 1124–1150
Wang J, Zhang Z, Wang X, Wu W, Jiang X. J Control Release, 2013, 1: 1–9
Lv S, Wu Y, Cai K, He H, Li Y, Lan M, Chen X, Cheng J, Yin L. J Am Chem Soc, 2018, 1: 1235–1238
Liu C, Wan T, Wang H, Zhang S, Ping Y, Cheng Y. Sci Adv, 2019, 5: eaaw8922
Ishikawa K, Takenaga K, Akimoto M, Koshikawa N, Yamaguchi A, Imanishi H, Nakada K, Honma Y, Hayashi JI. Science, 2008, 1: 661–664
Trachootham D, Alexandre J, Huang P. Nat Rev Drug Discov, 2009, 1: 579–591
Song CC, Ji R, Du FS, Liang DH, Li ZC. ACS Macro Lett, 2013, 1: 273–277
He H, Chen Y, Li Y, Song Z, Zhong Y, Zhu R, Cheng J, Yin L. Adv Funct Mater, 2018, 28: 1706710
Lee S, Stubelius A, Hamelmann N, Tran V, Almutairi A. ACS Appl Mater Interfaces, 2018, 1: 40378–40387
Hoang TT, Smith TP, Raines RT. Angew Chem Int Ed, 2017, 1: 2619–2622
Liu C, Shao N, Wang Y, Cheng Y. Adv Healthc Mater, 2016, 1: 584–592
Piest M, Engbersen JFJ. J Control Release, 2011, 1: 331–340
Liu X, Xiang J, Zhu D, Jiang L, Zhou Z, Tang J, Liu X, Huang Y, Shen Y. Adv Mater, 2016, 1: 1743–1752
Xiang J, Liu X, Zhou Z, Zhu D, Zhou Q, Piao Y, Jiang L, Tang J, Liu X, Shen Y. ACS Appl Mater Interfaces, 2018, 1: 43352–43362
Zhu D, Yan H, Liu X, Xiang J, Zhou Z, Tang J, Liu X, Shen Y. Adv Funct Mater, 2017, 27: 1606826
Zhang Z, Wang Q, Liu Q, Zheng Y, Zheng C, Yi K, Zhao Y, Gu Y, Wang Y, Wang C, Zhao X, Shi L, Kang C, Liu Y. Adv Mater, 2019, 31: 1905751
Zhou L, Ding H, Zhao W, Hu S. Spectrochim Acta Part A, 2019, 1: 529–534
Sun X, Odyniec ML, Sedgwick AC, Lacina K, Xu S, Qiang T, Bull SD, Marken F, James TD. Org Chem Front, 2017, 1: 1058–1062
Van de Bittner GC, Dubikovskaya EA, Bertozzi CR, Chang CJ. Proc Natl Acad Sci USA, 2010, 1: 21316–21321
Viger ML, Collet G, Lux J, Nguyen Huu VA, Guma M, Foucault-Collet A, Olejniczak J, Joshi-Barr S, Firestein GS, Almutairi A. Biomaterials, 2017, 1: 119–131
Zhang G, Liao Q, Liu Y, Wang L, Gou H, Ke C, Huang X, Xi K, Jia X. Nanoscale, 2018, 1: 5503–5514
Mo R, Jiang T, Sun W, Gu Z. Biomaterials, 2015, 1: 67–74
Mo R, Jiang T, Gu Z. Angew Chem Int Ed, 2014, 1: 5815–5820
Qian C, Chen Y, Zhu S, Yu J, Zhang L, Feng P, Tang X, Hu Q, Sun W, Lu Y, Xiao X, Shen QD, Gu Z. Theranostics, 2016, 1: 1053–1064
Jiang C, Qi Z, Jia H, Huang Y, Wang Y, Zhang W, Wu Z, Yang H, Liu J. Biomacromolecules, 2019, 1: 478–489
Yoshinaga N, Ishii T, Naito M, Endo T, Uchida S, Cabral H, Osada K, Kataoka K. J Am Chem Soc, 2017, 1: 18567–18575
Zhou Z, Zhang Q, Zhang M, Li H, Chen G, Qian C, Oupicky D, Sun M. Theranostics, 2018, 1: 4604–4619
Zhou Z, Zhang M, Liu Y, Li C, Zhang Q, Oupicky D, Sun M. Biomacromolecules, 2018, 1: 3776–3787
Xu Z, Zeng G, Liu Y, Zhang X, Cheng J, Zhang J, Ma Z, Miao M, Zhang D, Wei Y. Dyes Pigments, 2019, 1: 559–563
Minami T, Emami F, Nishiyabu R, Kubo Y, Anzenbacher P. Chem Commun, 2016, 1: 7838–7841
Wang L, Yuan L, Zeng X, Peng J, Ni Y, Er JC, Xu W, Agrawalla BK, Su D, Kim B, Chang YT. Angew Chem Int Ed, 2016, 1: 1773–1776
Li J, Zhang N, Sun Q, Bai Z, Zheng J. Talanta, 2016, 1: 379–386
Gabrielli L, Carril M, Padro D, Mancin F. Chem Eur J, 2018, 1: 13036–13042
Qian CG, Zhu S, Feng PJ, Chen YL, Yu JC, Tang X, Liu Y, Shen QD. ACS Appl Mater Interfaces, 2015, 1: 18581–18589
Feng P, Chen Y, Zhang L, Qian CG, Xiao X, Han X, Shen QD. ACS Appl Mater Interfaces, 2018, 1: 4359–4368
Guo X, Wei X, Chen Z, Zhang X, Yang G, Zhou S. Prog Mater Sci, 2020, 107: 100599
Zhou Z, Shen Y, Tang J, Fan M, Van Kirk EA, Murdoch WJ, Radosz M. Adv Funct Mater, 2009, 1: 3580–3589
Pan L, He Q, Liu J, Chen Y, Ma M, Zhang L, Shi J. J Am Chem Soc, 2012, 1: 5722–5725
Pan L, Liu J, He Q, Shi J. Adv Mater, 2014, 1: 6742–6748
Zhu YX, Jia HR, Pan GY, Ulrich NW, Chen Z, Wu FG. J Am Chem Soc, 2018, 1: 4062–4070
Pan L, Liu J, Shi J. Adv Funct Mater, 2014, 1: 7318–7327
Tang R, Wang M, Ray M, Jiang Y, Jiang Z, Xu Q, Rotello VM. J Am Chem Soc, 2017, 1: 8547–8551
Wu R, Liu J, Chen D, Pan J. ACS Appl Nano Mater, 2019, 1: 4333–4341
Acknowledgements
This work was supported by the National Key Research and Development Program of China (2017YFA0701301, 2017YFA0205400), the National Natural Science Foundation of China (51690153, 21720102005, 51803089), and the Program for Changjiang Scholars and Innovative Research Team in University and the Fundamental Research Funds for the Central Universities.
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Chen, W., Zhen, X., Wu, W. et al. Responsive boron biomaterials and their biomedical applications. Sci. China Chem. 63, 648–664 (2020). https://doi.org/10.1007/s11426-019-9699-3
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DOI: https://doi.org/10.1007/s11426-019-9699-3