Preparation of Chlorine e6-Conjugated Single-Wall Carbon Nanotube for Photodynamic Therapy

Dong Jin Lee; So Young Park; Young Taik Oh; Nam Muk Oh; Kyung Taek Oh; Yu Seok Youn; Eun Seong Lee

Macromolecular Research, Vol.19, No.8, 848-852, August, 2011

DOI10.1007/s13233-011-0816-x Export Citation

Preparation of Chlorine e6-Conjugated Single-Wall Carbon Nanotube for Photodynamic Therapy

Dong Jin Lee¹, So Young Park¹, Young Taik Oh², Nam Muk Oh¹, Kyung Taek Oh³, Yu Seok Youn⁴, and Eun Seong Lee^{1, 5, †}

¹Division of Biotechnology, The Catholic University of Korea, Gyeonggi, 420-743, Korea
²Department of Diagnostic Radiology, Yonsei University College of Medicine, Seoul, 120-752, Korea
³College of Pharmacy, Chung-Ang University, Seoul, 155-756, Korea
⁴College of Pharmacy, Pusan National University, Busan, 609-735, Korea
⁵The Catholic Institute for Advanced Biomaterials, Gyeonggi, 420-743, Korea

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We fabricated single-wall carbon nanotubes (SWNTs) modified with chlorine e6 (as a photosensitizing drug: Ce6) and poly(ethylene glycol) (PEG, as a polymeric stabilizer) were fabricated to develop a light-sensitive nanovehicle for tumor treatment. The carboxyl group of Ce6 and poly(ethylene glycol) (PEG) was coupled with aminated SWNT via N,N'-dicyclohexyl carbodiimide (DCC)- and N-hydroxysuccinimide (NHS)-mediated amide formation. During light irradiation, singlet oxygen generation from Ce6 coupled to the SWNTs was reduced due to the quenching effect of SWNTs for Ce6. Unlike free Ce6, Ce6 coupled to the SWNTs accumulated to a significant degree in the tumor site, reflecting its pharmaceutical potential under in vivo conditions. This might become a potential carrier system for improving photodynamic therapy.

Keywords:single-wall carbon nanotube;chlorine e6;poly(ethylene glycol);photodynamic therapy.

[References]

Liu Z, Chen K, Davis C, Sherlock S, Cao Q, Chen X, Dai H, Cancer Res., 68, 6552 (2008)
Venkatesan J, Kim SK, Mar. Drugs, 8, 2252 (2010)
Chen X, Kis A, Zettl A, Bertozzi CR, Proc. Natl. Acad. Sci. U.S.A., 104, 8218 (2007)
Mantha S, Pedrosa VA, Olsen EV, Davis VA, Simonian AL, Langmuir, 26(24), 19114 (2010)
David-Pur M, Shein M, Hanein Y, Methods Mol. Biol., 625, 171 (2010)
Yang K, Zhang S, Zhang G, Sun X, Lee ST, Liu Z, Nano Lett., 10, 3318 (2010)
Liang F, Chen B, Curr. Med. Chem., 17, 10 (2010)
Zhang X, Meng L, Lu Q, Fei Z, Dyson PJ, Biomaterials, 30, 6041 (2009)
Lay CL, Liu HQ, Tan HR, Liu Y, Nanotechnology, 21, 65101 (2010)
Zhuo Y, Yuan R, Chai YQ, Hong CL, Analyst, 135, 2036 (2010)
He J, Liu H, Pang P, Cao D, Lindsay S, J. Phys. Condens. Matter, 22, 454112 (2010)
Ruggiero A, Villa CH, Holland JP, Sprinkle SR, May C, Lewis JS, Scheinberg DA, McDevitt MR, Int. J. Nanomedicine, 5, 783 (2010)
Poland CA, Duffin R, Kinloch I, Maynard A, Wallace WAH, Seaton A, Stone V, Brown S, MacNee W, Donaldson K, Nat. Nanotechnol., 3(7), 423 (2008)
Sayes CM, Liang F, Hudson JL, Mendez J, Guo W, Beach JM, Moore VC, Doyle CD, West JL, Billups WE, Ausman KD, Colvin VL, Toxicol. Lett., 161, 135 (2006)
Nel A, Xia T, Maedler L, Li N, Science, 311, 622 (2006)
Bae BC, Na K, Biomaterials, 31, 6325 (2010)
Koo H, Lee H, Lee S, Min KH, Kim MS, Lee DS, Choi Y, Kwon IC, Kim K, Jeong SY, Chem. Commun., 46, 5668 (2010)
Janardhanan SK, Narayan S, Abbineni G, Hayhurst A, Mao C, Mol. Cancer Ther., 9, 2524 (2010)
Park SY, Baik HJ, Oh YT, Oh KT, Youn YS, Lee ES, Angew. Chem.-Int. Edit., 50, 1644 (2011)
Chin WW, Praveen T, Heng PW, Olivo M, Eur. J. Pharm. Biopharm., 76, 245 (2010)
Zalipsky S, Barany G, J. Bioact. Compat. Polym., 5, 227 (1990)
Ahn YS, Baik HJ, Lee BR, Lee ES, Oh KT, Lee DH, Youn YS, Macromol. Res., 18(8), 747 (2010)
Lee SH, Baek HH, Kim JH, Choi SW, Macromol. Res., 17(12), 1010 (2009)
Emmenegger CR, Brynda E, Riedel T, Sedlakova Z, Houska M, Alles AB, Langmuir, 25(11), 6328 (2009)
Gomes A, Fernandes E, Lima JLFC, J. Biochem. Biophys. Methods, 65, 45 (2005)
Yang RH, Jin JY, Chen Y, Shao N, Kang HZ, Xiao Z, Tang ZW, Wu YR, Zhu Z, Tan WH, J. Am. Chem. Soc., 130(26), 8351 (2008)
Hamblin MR, Miller JL, Rizvi I, Ortel B, Maytin EV, Hasan T, Cancer Res., 61, 7155 (2001)
Maeda H, Bioconjugate Chem., 21, 797 (2010)

[1] Liu Z, Chen K, Davis C, Sherlock S, Cao Q, Chen X, Dai H, Cancer Res., 68, 6552 (2008)

[2] Venkatesan J, Kim SK, Mar. Drugs, 8, 2252 (2010)

[3] Chen X, Kis A, Zettl A, Bertozzi CR, Proc. Natl. Acad. Sci. U.S.A., 104, 8218 (2007)

[4] Mantha S, Pedrosa VA, Olsen EV, Davis VA, Simonian AL, Langmuir, 26(24), 19114 (2010)

[5] David-Pur M, Shein M, Hanein Y, Methods Mol. Biol., 625, 171 (2010)

[6] Yang K, Zhang S, Zhang G, Sun X, Lee ST, Liu Z, Nano Lett., 10, 3318 (2010)

[7] Liang F, Chen B, Curr. Med. Chem., 17, 10 (2010)

[8] Zhang X, Meng L, Lu Q, Fei Z, Dyson PJ, Biomaterials, 30, 6041 (2009)

[9] Lay CL, Liu HQ, Tan HR, Liu Y, Nanotechnology, 21, 65101 (2010)

[10] Zhuo Y, Yuan R, Chai YQ, Hong CL, Analyst, 135, 2036 (2010)

[11] He J, Liu H, Pang P, Cao D, Lindsay S, J. Phys. Condens. Matter, 22, 454112 (2010)

[12] Ruggiero A, Villa CH, Holland JP, Sprinkle SR, May C, Lewis JS, Scheinberg DA, McDevitt MR, Int. J. Nanomedicine, 5, 783 (2010)

[13] Poland CA, Duffin R, Kinloch I, Maynard A, Wallace WAH, Seaton A, Stone V, Brown S, MacNee W, Donaldson K, Nat. Nanotechnol., 3(7), 423 (2008)

[14] Sayes CM, Liang F, Hudson JL, Mendez J, Guo W, Beach JM, Moore VC, Doyle CD, West JL, Billups WE, Ausman KD, Colvin VL, Toxicol. Lett., 161, 135 (2006)

[15] Nel A, Xia T, Maedler L, Li N, Science, 311, 622 (2006)

[16] Bae BC, Na K, Biomaterials, 31, 6325 (2010)

[17] Koo H, Lee H, Lee S, Min KH, Kim MS, Lee DS, Choi Y, Kwon IC, Kim K, Jeong SY, Chem. Commun., 46, 5668 (2010)

[18] Janardhanan SK, Narayan S, Abbineni G, Hayhurst A, Mao C, Mol. Cancer Ther., 9, 2524 (2010)

[19] Park SY, Baik HJ, Oh YT, Oh KT, Youn YS, Lee ES, Angew. Chem.-Int. Edit., 50, 1644 (2011)

[20] Chin WW, Praveen T, Heng PW, Olivo M, Eur. J. Pharm. Biopharm., 76, 245 (2010)

[21] Zalipsky S, Barany G, J. Bioact. Compat. Polym., 5, 227 (1990)

[22] Ahn YS, Baik HJ, Lee BR, Lee ES, Oh KT, Lee DH, Youn YS, Macromol. Res., 18(8), 747 (2010)

[23] Lee SH, Baek HH, Kim JH, Choi SW, Macromol. Res., 17(12), 1010 (2009)

[24] Emmenegger CR, Brynda E, Riedel T, Sedlakova Z, Houska M, Alles AB, Langmuir, 25(11), 6328 (2009)

[25] Gomes A, Fernandes E, Lima JLFC, J. Biochem. Biophys. Methods, 65, 45 (2005)

[26] Yang RH, Jin JY, Chen Y, Shao N, Kang HZ, Xiao Z, Tang ZW, Wu YR, Zhu Z, Tan WH, J. Am. Chem. Soc., 130(26), 8351 (2008)

[27] Hamblin MR, Miller JL, Rizvi I, Ortel B, Maytin EV, Hasan T, Cancer Res., 61, 7155 (2001)

[28] Maeda H, Bioconjugate Chem., 21, 797 (2010)