pH-Sensitive Polypeptide Conjugated with Carborane Clusters and Cyanine for NIR Bioimaging and Multi-Therapies

Zheng Ruan; Pan Yuan; Titao Jing; Tao Xing; Lifeng Yan

Macromolecular Research, Vol.26, No.3, 270-277, March, 2018

DOI10.1007/s13233-018-6034-z Export Citation

pH-Sensitive Polypeptide Conjugated with Carborane Clusters and Cyanine for NIR Bioimaging and Multi-Therapies

Zheng Ruan^†, Pan Yuan, Titao Jing, Tao Xing^{1, †}, and Lifeng Yan^†

CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemical Physics, iChEM, University of Science and Technology of China, Jinzai Road 96#, Hefei, 230026, Anhui, P. R. China
¹Institute of System and Engineering, Chinese Academy of Engineering Physics, Mianyang, P. R. China

E-mail:, ,

A novel pH-sensitive carborane and cyanine dye conjugated polypeptide and its micelles has been designed and synthesized for potential near infrared fluorescence imaging-guided boron neutron capture therapy (BNCT). The amphiphilic polymer we synthesized with tertiary amine as functional group could self-assemble to micelle nanoparticles at neutral pH, and responsive to acidic solution for the disassembly of the micelles for drug release. The tertiary amine sensitive induced process was observed via dynamic light scattering (DLS) and transmission electron microscopy (TEM). The efficiency of cell killing ability is studied by MTT assays and fluorescence microscope measurement, indicating a new intelligent system for potential NIR imaging-guided therapy.

Keywords:pH-sensitive;carborane;tertiary amine;imaging-guided;boron neutron capture therapy

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[1] Barth RF, Coderre JA, Vicente MGH, Blue TE, Clin. Cancer Res., 11, 3987 (2005)

[2] Salt C, Lennox AJ, Takagaki M, Maguire JA, Hosmane NS, Russ. Chem. Bull., 53, 1871 (2004)

[3] Mitin VN, Kulakov VN, Khokhlov VF, Sheino IN, Arnopolskaya AM, Kozlovskaya NG, Zaitsev KN, Portnov AA, Appl. Radiat. Isot., 67, S299 (2009)

[4] Armstrong AF, Valliant JF, Dalton Trans., 4240 (2007).

[5] Soloway AH, Tjarks W, Barnum BA, Rong FG, Barth RF, Codogni IM, Wilson JG, Chem. Rev., 98(4), 1515 (1998)

[6] Coderre JA, Turcotte JC, Riley KJ, Binns PJ, Harling OK, Kiger WS, Technol. Cancer Res. Treat., 2, 355 (2003)

[7] Kim DW, Lee CM, Kim NH, Lee SY, Lee MY, Choi ES, Park SA, Kim CG, Hwang H, Lim ST, Sohn MH, Jeong HJ, Macromol. Res., 22(3), 272 (2014)

[8] Barth RF, Vicente MGH, Harling OK, Kiger WS, Riley KJ, Binns PJ, Wagner FM, Suzuki M, Aihara T, Kato I, Kawabata S, Radiat. Oncol., 7 (2012)

[9] Alberti D, Toppino A, Crich SG, Meraldi C, Prandi C, Protti N, Bortolussi S, Altieri S, Aime S, Deagostino A, Org. Biomol. Chem., 12, 2457 (2014)

[10] Tietze LF, Griesbach U, Bothe U, Nakamura H, Yamamoto Y, Chembiochem, 3, 219 (2002)

[11] Yoo J, Do Y, Dalton Trans., 4978 (2009).

[12] Vinas C, Teixidor F, Nunez R, Inorg. Chim. Acta., 409, 12 (2014)

[13] Tachikawa S, Miyoshi T, Koganei H, El-Zaria ME, Vinas C, Suzuki M, Ono K, Nakamura H, Chem. Commun., 50, 12325 (2014)

[14] Chen GJ, Yang JY, Lu G, Liu PC, Chen QJ, Xie ZW, Wu C, Mol. Pharmaceutics, 11, 3291 (2014)

[15] Xiong HJ, Zhou DF, Qi YX, Zhang ZY, Xie ZG, Chen XS, Jing XB, Meng FB, Huang YB, Biomacromolecules, 16(12), 3980 (2015)

[16] Matsumura Y, Maeda H, Cancer Res., 46, 6387 (1986)

[17] Cho YW, Kim YS, Kim IS, Park RW, Oh SJ, Moon DH, Kim SY, Kwon IC, Macromol. Res., 16(1), 15 (2008)

[18] Cho YW, Kim K, Park K, Kwon IC, Macromol. Res., 22(9), 926 (2014)

[19] Lee JM, KIm OH, Shim SE, Lee BH, Choe S, Macromol. Res., 13(3), 236 (2005)

[20] Ruan Z, Liu L, Jiang W, Li SY, Wang YC, Yan LF, Biomater. Sci-Uk, 5, 313 (2017)

[21] Ruan Z, Liu L, Fu L, Xing T, Yan L, Polym. Chem., 7, 4411 (2016)

[22] Fu L, Liu L, Ruan Z, Zhang H, Yan L, RSC Adv., 6, 40312 (2016)

[23] Jin GR, Feng GX, Qin W, Tang BZ, Liu B, Li K, Chem. Commun., 52, 2752 (2016)

[24] Fu LY, Sun CY, Yan LF, ACS Appl. Mater. Interfaces, 7, 2104 (2015)

[25] Xing T, Yang X, Wang F, Lai B, Yan L, J. Mater. Chem., 22, 22290 (2012)