화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.26, No.12, 1074-1084, December, 2018
DOI10.1007/s13233-018-6156-3  Export Citation
Molecular Engineering of Metal-Organic Cycles/Cages for Drug Delivery
Nicola Judge, Lang Wang, Yannis Yan Lum Ho, and Yufeng Wang†
  • Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
E-mail:
The assembly of nanoscale materials with well-defined size and shape is an intriguing approach to aid in drug design and delivery. Of the various nano-structures that have been synthesised, metal-organic cycles and cages (MOCs), featuring great structural versatility, have emerged as promising components in cancer chemotherapeutics. We review the recent progress of exploiting self-assembled MOCs as anticancer drugs as well as drug carriers. Particularly molecular engineering designs allow MOCs to carry drugs with specificity, and interface with biological systems whilst possessing the desired stability, cytotoxicity, and compatibility. A special focus is given to the functionalization method of integrating MOCs with polymers, leading to the synthesis of colloidal nanoparticles-micelles and vesicles-that possess combined properties and extended system tunability.
Keywords:metal-organic cycles/cages (MOC);self-assembly;nanoparticles;drug delivery;cancer therapeutics
  1. Cook TR, Stang PJ, Chem. Rev., 115(15), 7001 (2015)
  2. Chakrabarty R, Mukherjee PS, Stang PJ, Chem. Rev., 111(11), 6810 (2011)
  3. Breiner B, Clegg JK, Nitschke JR, Chem. Sci., 2, 51 (2010)
  4. Pluth MD, Bergman RG, Raymond KN, Accounts Chem. Res., 42, 1650 (2009)
  5. Yoshizawa M, Klosterman JK, Fujita M, Angew. Chem.-Int. Edit., 48, 3418 (2009)
  6. Yasuhide I, Tatsuhiko A, Makoto F, Nat. Chem., 2, 780 (2010)
  7. Zhang MM, Saha ML, Wang M, Zhou ZX, Song B, Lu CJ, Yan XZ, Li XP, Huang FH, Yin SC, Stang PJ, J. Am. Chem. Soc., 139(14), 5067 (2017)
  8. Yasuhide I, Masaki K, Makoto F, Nat. Chem., 3, 349 (2011)
  9. Stang P, Olenyuk B, Accounts Chem. Res., 30, 502 (1997)
  10. Tominaga M, Suzuki K, Kawano M, Kusukawa T, Ozeki T, Sakamoto S, Yamaguchi K, Fujita M, Angew. Chem.-Int. Edit., 43, 5621 (2004)
  11. Liao P, Langloss BW, Johnson AM, Knudsen ER, Tham FS, Julian RR, Hooley RJ, Chem. Commun., 46, 4932 (2010)
  12. Fujita D, Ueda Y, Sato S, Yokoyama H, Mizuno N, Kumasaka T, Fujita M, Chem, 1, 91 (2016)
  13. Fujita D, Ueda Y, Sato S, Mizuno N, Kumasaka T, Fujita M, Nature, 540(7634), 563 (2016)
  14. Lewis JEM, Gavey EL, Cameron SA, Crowley JD, Chem. Sci., 3, 778 (2012)
  15. Schmidt A, Molano V, Hollering M, Pothig A, Casini A, Kuhn FE, Chem. Eur. J., 22, 2253 (2016)
  16. Robby AP, Joseph MD, Nat. Rev. Drug Discov., 9, 615 (2010)
  17. Hongmin C, Weizhong Z, Guizhi Z, Jin X, Xiaoyuan C, Nat. Rev. Mater., 2, 17024 (2017)
  18. Eryazici I, Moorefield CN, Newkome GR, Chem. Rev., 108(6), 1834 (2008)
  19. McNeill SM, Preston D, Lewis JEM, Robert A, Knerr-Rupp K, Graham DO, Wright JR, Giles GI, Crowley JD, Dalton Trans., 44, 11129 (2015)
  20. Preston D, McNeill SM, Lewis JEM, Giles GI, Crowley JD, Dalton Trans., 45, 8050 (2016)
  21. Paul LEH, Therrien B, Furrer J, Inorg. Chem., 51(2), 1057 (2012)
  22. Vajpayee V, Song YH, Yang YJ, Kang SC, Cook TR, Kim DW, Lah MS, Kim IS, Wang M, Stang PJ, Chi KW, Organometallics, 30, 6482 (2011)
  23. Kai S, Shigeta T, Kojima T, Hiraoka S, Chem. Asian J., 12, 3203 (2017)
  24. Kai S, Marti-Centelles V, Sakuma Y, Mashiko T, Kojima T, Nagashima U, Tachikawa M, Lusby PJ, Hiraoka S, Chem. Eur. J., 24, 663 (2018)
  25. Gupta G, Das A, Park KC, Tron A, Kim H, Mun J, Mandal N, Chi KW, Lee CY, Inorg. Chem., 56, 4616 (2017)
  26. Yu G, Cook TR, Li Y, Yan X, Wu D, Shao L, Shen J, Tang G, Huang F, Chen X, Stang PJ, Proc. Natl. Acad. Sci. U.S.A., 113, 13720 (2016)
  27. Mounir M, Lorenzo J, Ferrer F, Prieto MJ, Rossell O, Aviles FX, Moreno V, J. Inorg. Biochem., 101, 660 (2007)
  28. Franceschin M, Eur. J. Org. Chem., 14, 2225 (2009)
  29. Kieltyka R, Englebienne P, Fakhoury J, Autexier C, Moitessier N, Sleiman HF, J. Am. Chem. Soc., 130(31), 10040 (2008)
  30. Barry NPE, Abd Karim KH, Vilar R, Therrien B, Dalton Trans., 10717 (2009).
  31. Mattson J, Govindaswamy P, Renfrew A, Dyson P, Stepnicka P, Suss-Fink G, Therrien B, Organometallics, 28, 4350 (2009)
  32. Barry N, Edafe F, Therrien B, Dalton Trans., 40, 7172 (2011)
  33. Therrien B, Suss-Fink G, Govindaswamy P, Renfrew AK, Dyson PJ, Angew. Chem.-Int. Edit., 47, 3773 (2008)
  34. Barry NPE, Edafe F, Dyson PJ, Therrien B, Dalton Trans., 39, 2816 (2010)
  35. Linares F, Galindo MA, Galli S, Romero MA, Navarro JAR, Barea E, Inorg. Chem., 48(15), 7413 (2009)
  36. Vajpayee V, Yang YJ, Kang SC, Kim H, Kim IS, Wang M, Stang PJ, Chi KW, Chem. Commun., 47, 5184 (2011)
  37. Mishra A, Jung H, Park JW, Kim HK, Kim H, Stang PJ, Chi KW, Organometallics, 31, 3519 (2012)
  38. Vajpayee V, Lee S, Kim SH, Kang SC, Cook TR, Kim H, Kim DW, Verma S, Lah MS, Kim IS, Wang M, Stang PJ, Chi KW, Dalton Trans., 42, 466 (2012)
  39. Vajpayee V, Song YH, Yang YJ, Kang SC, Kim H, Kim IS, Wang M, Stang PJ, Chi KW, Organometallics, 30, 3242 (2011)
  40. Vajpayee V, Song YH, Yang YJ, Kang SC, Kim H, Kim IS, Wang M, Cook TR, Stang PJ, Chi KW, Dalton Trans., 41, 3046 (2012)
  41. Cook T, Vajpayee V, Lee M, Stang P, Chi K, Accounts Chem. Res., 46, 2464 (2013)
  42. Ahmad N, Younus HA, Chughtai AH, Verpoort F, Chem. Soc. Rev., 44, 9 (2014)
  43. Vardhan H, Yusubov M, Verpoort F, Coord. Chem. Rev., 306, 171 (2016)
  44. Ahmedova A, Momekova D, Yamashina M, Shestakova P, Momekov G, Akita M, Yoshizawa M, Chem. Asian J., 11, 474 (2016)
  45. Barry NPE, Zava O, Dyson PJ, Therrien B, J. Org. Chem., 705, 1 (2012)
  46. Ivan VG, Pollock JB, Swati K, Timothy RC, Peter JS, Bogdan ZO, Proc. Natl. Acad. Sci., 111, 18448 (2014)
  47. Zhou J, Zhang YZ, Yu GC, Crawley MR, Fulong CRP, Friedman AE, Sengupta S, Sun JF, Li Q, Huang FH, Cook TR, J. Am. Chem. Soc., 140(24), 7730 (2018)
  48. McConnell AJ, Wood CS, Neelakandan PP, Nitschke JR, Chem. Rev., 115(15), 7729 (2015)
  49. Suzuki K, Iida J, Sato S, Kawano M, Fujita M, Angew. Chem.-Int. Edit., 47, 5780 (2008)
  50. Tominaga M, Suzuki K, Murase T, Fujita M, J. Am. Chem. Soc., 127(34), 11950 (2005)
  51. Kikuchi T, Sato S, Fujita M, J. Am. Chem. Soc., 132(45), 15930 (2010)
  52. Lewis JEM, Elliott ABS, McAdam CJ, Gordon KC, Crowley JC, Chem. Sci., 5, 1833 (2014)
  53. Wang HN, Meng X, Yang GS, Wang XL, Shao KZ, Su ZM, Wang CG, Chem. Commun., 47, 7128 (2011)
  54. Yi JW, Barry NPE, Furrer MA, Zava O, Dyson PJ, Therrien B, Kim BH, Bioconjug. Chem., 23, 461 (2012)
  55. Preston D, Lewis JEM, Crowley JD, J. Am. Chem. Soc., 139(6), 2379 (2017)
  56. Cullen W, Turega S, Hunter CA, Ward MD, Chem. Sci., 6, 625 (2014)
  57. Zheng YR, Suntharalingam K, Johnstone TC, Lippard SJ, Chem. Sci., 6, 1189 (2015)
  58. Holliday BJ, Mirkin CA, Angew. Chem.-Int. Edit., 40, 2022 (2001)
  59. Schmidt A, Hollering M, Drees M, Casini A, Khn FE, Dalton Trans., 45, 8556 (2016)
  60. Biedermann F, Elmalem E, Ghosh I, Nau WM, Scherman OA, Angew. Chem.-Int. Edit., 51, 7739 (2012)
  61. Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ, Chem. Commun., 18, 1740 (2001)
  62. Hong Y, Lam JY, Tang BZ, Chem. Commun., 4332 (2009).
  63. Hong Y, Lam JWY, Tang BZ, Chem. Soc. Rev., 40, 5361 (2011)
  64. Liang J, Tang BZ, Liu B, Chem. Soc. Rev., 44, 2798 (2015)
  65. Zhao Z, Lam JWY, Tang BZ, J. Mater. Chem., 22, 23726 (2012)
  66. Yan X, Cook TR, Wang P, Huang F, Stang PJ, Nat. Chem., 7, 342 (2015)
  67. Zhang T, Zhang GL, Yan QQ, Zhou LP, Cai LX, Guo XQ, Sun QF, Inorg. Chem., 57, 3596 (2017)
  68. Yan QQ, Hu SJ, Zhang GL, Zhang T, Zhou LP, Sun QF, Molecules, 23, 363 (2018)
  69. Zhang M, Li S, Yan X, Zhou Z, Saha ML, Wang YC, Stang PJ, Proc. Natl. Acad. Sci. U.S.A., 113, 11100 (2016)
  70. Zhao GJ, Northrop BH, Stang PJ, Han KL, J. Phys. Chem. A,, 114, 3418 (2010)
  71. Pollock JB, Cook TR, Stang PJ, J. Am. Chem. Soc., 134(25), 10607 (2012)
  72. Pollock JB, Schneider GL, Cook TR, Davies AS, Stang PJ, J. Am. Chem. Soc., 135, 13676 (2013)
  73. Webber WJ, Appel EA, Vinciguerra B, Cortinas AB, Thapa LS, Jhunjhunwala S, Isaacs L, Langer R, Anderson DG, Proc. Natl. Acad. Sci. U.S.A., 113, 14189 (2016)
  74. Yu GC, Zhang MM, Saha ML, Mao ZW, Chen J, Yao Y, Zhou ZJ, Liu YJ, Gao CY, Huang FH, Chen XY, Stang PJ, J. Am. Chem. Soc., 139(44), 15940 (2017)
  75. Datta S, Misra SK, Saha ML, Lahiri N, Louie J, Pan D, Stang PJ, Proc. Natl. Acad. Sci. U.S.A., 115, 8087 (2018)
  76. Zhao D, Tan SW, Yuan DQ, Lu WG, Rezenom YH, Jiang HL, Wang LQ, Zhou HC, Adv. Mater., 23(1), 90 (2011)
  77. Foster JA, Parker RM, Belenguer AM, Kishi N, Sutton S, Abell C, Nitschke JR, J. Am. Chem. Soc., 137(30), 9722 (2015)
  78. Ibukuro F, Kusukawa T, Fujita M, J. Am. Chem. Soc., 120(33), 8561 (1998)
  79. Yue Z, Wang H, Bowers DJ, Gao M, Stilgenbauer M, Nielsen F, Shelley JT, Zheng YR, Dalton Trans., 47, 670 (2018)
  80. Samanta SK, Moncelet D, Briken V, Isaacs L, J. Am. Chem. Soc., 138(43), 14488 (2016)
  81. Samanta SK, Quigley J, Vinciguerra B, Briken V, Isaacs L, J. Am. Ceram. Soc., 139, 9066 (2017)