Supramolecular assembly based on host.guest interaction between beta-cyclodextrin and adamantane for specifically targeted cancer imaging

Deok-Won Lee; Jihoon Jo; Danbi Jo; Jangho Kim; Jung-Joon Min; Dae Hyeok Yang; Hoon Hyun

Journal of Industrial and Engineering Chemistry, Vol.57, 37-44, January, 2018

DOI10.1016/j.jiec.2017.08.005 Export Citation

Supramolecular assembly based on host.guest interaction between beta-cyclodextrin and adamantane for specifically targeted cancer imaging

Deok-Won Lee, Jihoon Jo¹, Danbi Jo¹, Jangho Kim², Jung-Joon Min³, Dae Hyeok Yang^{4, †}, and Hoon Hyun^{1, †}

Department of Oral and Maxillofacial Surgery, Kyung Hee University Dental Hospital at Gangdong, Kyung Hee University, Seoul 05278, South Korea
¹Department of Biomedical Sciences, Chonnam National University Medical School, Gwangju 61469, South Korea
²Department of Rural and Biosystems Engineering, Chonnam National University, Gwangju 61186, South Korea
³Department of Nuclear Medicine, Chonnam National University Medical School, Gwangju 61469, South Korea
⁴Institute of Cell and Tissue Engineering, College of Medicine, The Catholic University of Korea, Seoul 06591, South Korea

E-mail:,

Accurate diagnosis of tumor and targeted drug delivery are prerequisites to effectively treat tumors with minimum side effects. In this study, beta-cyclodextrin (β-CD), polyethylene glycol (PEG), and folic acid (FA) were combined as a flatform (CDPF) to effectively transport adamantane (ADM) and near-infrared fluorophore (NIRF) conjugate (ADM-NIRF) to tumor target site. Using a tumor-bearing xenograft mouse model, the supramolecular assembly exhibited excellent tumor targetability because the FA component could strongly bind to folate-receptors overexpressed in the membrane of MCF7 human breast adenocarcinoma cells compared to ADM-NIRF. These results indicate that CDPF-ADM-NIRF has potential as a tumor diagnosis agent for clinical use.

Keywords:beta-Cyclodextrin;Adamantane;Folic acid;Polyethylene glycol;Tumor targetability

[References]

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Zheng JH, Min JJ, Chonnam Med. J., 52, 173 (2016)
Jo D, Hyun H, Chonnam Med. J., 53, 95 (2017)
Owens EA, Hyun H, Dost TL, Lee JH, Park G, Pham DH, Park MH, Choi HS, Henary M, J. Med. Chem., 59, 5311 (2016)
Hyun H, Owens EA, Wada H, Levitz A, Park G, Park MH, Frangioni JV, Henary M, Choi HS, Angew. Chem.-Int. Edit., 54, 8648 (2015)
Owens EA, Hyun H, Tawney JG, Choi HS, Henary M, J. Med. Chem., 58, 4348 (2015)
Hyun H, Wada H, Bao K, Gravier J, Yadav Y, Laramie M, Henary M, Frangioni JV, Choi HS, Angew. Chem.-Int. Edit., 53, 10668 (2014)
Kim SH, In I, Park SY, Biomacromolecules, 18(6), 1825 (2017)
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Choi HS, Nasr K, Alyabyev S, Feith D, Lee JH, Kim SH, Ashitate Y, Hyun H, Patonay G, Strekowski L, Henary M, Frangioni JV, Angew. Chem.-Int. Edit., 50, 6258 (2011)
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Hyun H, Bordo MW, Nasr K, Feith D, Lee JH, Kim SH, Ashitate Y, Moffitt LA, Rosenberg M, Henary M, Choi HS, Frangioni JV, Contrast Media Mol. Imaging, 7, 516 (2012)
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Hyun H, Park MH, Owens EA, Wada H, Henary M, Handgraaf HJ, Vahrmeijer AL, Frangioni JV, Choi HS, Nat. Med., 21, 192 (2015)
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[Referenced By]

[1] Grueneisen J, Naqarajah J, Buchbender C, Hoffmann O, Schaarschmidt BM, Poeppel T, Forsting M, Quick HH, Umutlu L, Kinner S, Invest. Radiol., 50, 505 (2015)

[2] Jadvar H, Colletti PM, Eur J. Radiol., 83, 84 (2014)

[3] Esabahy M, Heo GS, Lim SM, Sun GR, Wooley KL, Chem. Rev., 115(19), 10967 (2015)

[4] Zheng JH, Min JJ, Chonnam Med. J., 52, 173 (2016)

[5] Jo D, Hyun H, Chonnam Med. J., 53, 95 (2017)

[6] Owens EA, Hyun H, Dost TL, Lee JH, Park G, Pham DH, Park MH, Choi HS, Henary M, J. Med. Chem., 59, 5311 (2016)

[7] Hyun H, Owens EA, Wada H, Levitz A, Park G, Park MH, Frangioni JV, Henary M, Choi HS, Angew. Chem.-Int. Edit., 54, 8648 (2015)

[8] Owens EA, Hyun H, Tawney JG, Choi HS, Henary M, J. Med. Chem., 58, 4348 (2015)

[9] Hyun H, Wada H, Bao K, Gravier J, Yadav Y, Laramie M, Henary M, Frangioni JV, Choi HS, Angew. Chem.-Int. Edit., 53, 10668 (2014)

[10] Kim SH, In I, Park SY, Biomacromolecules, 18(6), 1825 (2017)

[11] Yang DH, Kim HJ, Kim JK, Chun HJ, Park K, J. Ind. Eng. Chem., 45, 156 (2017)

[12] Kang HM, Gravier J, Bao K, Wada H, Lee JH, Baek Y, El Fakhri G, Gioux S, Rubin BP, Coll JL, Choi HS, Adv. Mater., 28(37), 8162 (2016)

[13] Sharker SM, Kim SM, Kim SH, In I, Lee H, Park SY, J. Mater. Chem., 3, 5833 (2015)

[14] Jokerst JV, Lobovkina T, Zare RN, Gambhir SS, Nanomedicine, 6, 715 (2011)

[15] Tu Q, Zhang Y, Liu R, Wang JC, Li L, Nie N, Liu A, Wang L, Liu W, Wang X, Wang J, Curr. Med. Chem., 19, 3152 (2012)

[16] Laha D, Pramanik A, Chattopadhyay S, Dash SK, Roy S, Pramanik P, Karmakar P, RSC Adv., 5, 68169 (2015)

[17] Granadero D, Bordello J, Perez-Alvite MJ, Novo M, Al-Soufi W, Int. J. Mol. Sci., 11(1), 173 (2010)

[18] Choi HS, Nasr K, Alyabyev S, Feith D, Lee JH, Kim SH, Ashitate Y, Hyun H, Patonay G, Strekowski L, Henary M, Frangioni JV, Angew. Chem.-Int. Edit., 50, 6258 (2011)

[19] Hyun H, Henary M, Gao T, Narayana L, Owens EA, Lee JH, Park G, Wada H, Ashitate Y, Frangioni JY, Choi HS, Mol. Imaging Biol., 18, 52 (2016)

[20] Hyun H, Bordo MW, Nasr K, Feith D, Lee JH, Kim SH, Ashitate Y, Moffitt LA, Rosenberg M, Henary M, Choi HS, Frangioni JV, Contrast Media Mol. Imaging, 7, 516 (2012)

[21] Choi HS, Gibbs SL, Lee JH, Kim SH, Ashitate Y, Liu F, Hyun H, Park G, Xie Y, Bae S, Henery M, Frangioni JV, Nat. Biotechnol., 31, 148 (2013)

[22] Hyun H, Park MH, Owens EA, Wada H, Henary M, Handgraaf HJ, Vahrmeijer AL, Frangioni JV, Choi HS, Nat. Med., 21, 192 (2015)

[23] Moyers-Montoya E, Garcia-Casillas P, Vargas-Requena C, Escobedo-Gonzalez R, Martel-Estrada SA, Martinez-Perez CA, Polymer, 8, 395 (2016)

[24] Herzberger J, Frey H, Macromolecules, 48(22), 8144 (2015)

[25] Cheng D, Hong G, Wang W, Yuan R, Ai H, Shen J, Liang B, Gao J, Shuai X, J. Mater. Chem., 21, 4796 (2011)

[26] Han Y, Liu Y, Rockenbauer A, Zweier JL, Durana G, Villamena FA, J. Org. Chem., 74, 5369 (2009)

[27] Xu S, Olenyuk BZ, Okamoto CT, Hamm-Alvarez SF, Adv. Drug Deliv. Rev., 65, 121 (2013)

[28] Housman G, Byler S, Heerboth S, Lapinska K, Longacre M, Synder N, Sarkar S, Cancers, 6, 1769 (2014)

[29] Xue X, Liang XJ, Chin. J. Cancer, 31, 100 (2012)