Abstract
Curcumin is the physiologically and pharmacologically active component of turmeric (Curcuma longa L.) with attractive fluorescent property. However, the applications in live cell imaging field are restricted mainly due to the water-insolubility and cytotoxicity. To overcome this problem, curcumin-incorporated glycopolymers are synthesized by free radical copolymerization in this study. The glycopolymers are well-characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), UV-Vis absorption spectroscopy and photoluminescence spectroscopy. Furthermore, obtained glycopolymers are assayed by MTT assay and cell imaging for supporting the potential bio application. The MTT result indicates that the introduction of carbohydrate units can reduce the cytotoxicity of curcumin unit. The live cell imaging investigations reveal that the curcuminincorporated glycopolymers are good candidates for cell imaging and may find broad applications in biological areas such as biological diagnosis, imaging, and detection.
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O. Naksuriya, S. Okonogi, R. M. Schiffelers, and W. E. Hennink, Biomaterials, 35, 3365 (2014).
M. M. Yallapu, M. Jaggi, and S. C. Chauhan, Drug Discov. Today, 17, 71 (2012).
T. Esatbeyoglu, P. Huebbe, I. M. A. Ernst, D. Chin, A. E. Wagner, and G. Rimbach, Angew. Chem. Int. Ed., 51, 5308 (2012).
A. B. Kunnumakkara, P. Anand, and B. B. Aggarwal, Cancer Lett., 269, 199 (2008).
R. A. Sharma, A. J. Gescher, and W. P. Steward, Eur. J. Cancer, 41, 1955 (2005).
X. Wei, T. H. Senanayake, A. Bohling, and S. V. Vinogradov, Mol. Pharm., 11, 3112 (2014).
P. Anand, C. Sundaram, S. Jhurani, A. B. Kunnumakkara, and B. B. Aggarwal, Cancer Lett., 267, 133 (2008).
A. Beloqui, R. Coco, P. B. Memvanga, B. Ucakar, A. des Rieux, and V. Preat, Int. J. Pharm., 473, 203 (2014).
A. Mazumder, N. Neamati, S. Sunder, J. Schulz, H. Pertz, E. Eich, and Y. Pommier, J. Med. Chem., 40, 3057 (1997).
C. Changtam, H. P. de Koning, H. Ibrahim, M. S. Sajid, M. K. Gould, and A. Suksamrarn, Eur. J. Med. Chem., 45, 941 (2010).
J. Barry, M. Fritz, J. R. Brender, P. E. S. Smith, D.-K. Lee, and A. Ramamoorthy, J. Am. Chem. Soc., 131, 4490 (2009).
C. Changtam, P. Hongmanee, and A. Suksamrarn, Eur. J. Med. Chem., 45, 4446 (2010).
W. Shi, S. Dolai, S. Rizk, A. Hussain, H. Tariq, S. Averick, W. L'Amoreaux, A. El Ldrissi, P. Banerjee, and K. Raja, Org. Lett., 9, 5461 (2007).
X. Zhang, Y. Tian, Z. Li, X. Tian, H. Sun, H. Liu, A. Moore, and C. Ran, J. Am. Chem. Soc., 135, 16397 (2013).
B. B. Aggarwal and K. B. Harikumar, Int. J. Biochem. Cell Biol., 41, 40 (2009).
J. J. Pillai, A. K. T. Thulasidasan, R. J. Anto, D. N. Chithralekha, A. Narayanan, and G. S. V. Kumar, J. Nanobiotechnol., 12, 25 (2014).
A. P. Ranjan, A. Mukerjee, L. Helson, and J. K. Vishwanatha, J. Nanobiotechnol., 10 (2012).
B. Gogoi and N. Sen Sarma, J. Mater. Sci., 50, 7647 (2015).
M. A. Tomren, M. Masson, T. Loftsson, and H. H. Tonnesen, Int. J. Pharm., 338, 27 (2007).
M. Hasan, N. Belhaj, H. Benachour, M. Barberi-Heyob, C. J. F. Kahn, E. Jabbari, M. Linder, and E. Arab-Tehrany, Int. J. Pharm., 461, 519 (2014).
A. H. Matloob, S. Mourtas, P. Klepetsanis, and S. G. Antimisiaris, Int. J. Pharm., 476, 108 (2014).
T. T. T. Nguyen, C. Ghosh, S. G. Hwang, L. D. Tran, and J. S. Park, J. Mater. Sci., 48, 7125 (2013).
P. Koley and A. Pramanik, J. Mater. Sci., 49, 2000 (2014).
C. Chen and H. Wang, Macromol. Rapid Commun., 35, 1534 (2014).
M. M. Yallapu, M. Jaggi, and S. C. Chauhan, Macromol. Biosci., 10, 1141 (2010).
P. R. Dandawate, A. Vyas, A. Ahmad, S. Banerjee, J. Deshpande, K. V. Swamy, A. Jamadar, A.C. Dumhe-Klaire, S. Padhye, and F. H. Sarkar, Pharm. Res., 29, 1775 (2012).
C. Y. Gong, S. Y. Deng, Q. J. Wu, M. L. Xiang, X. W. Wei, L. Li, X. Gao, B. L. Wang, L. Sun, Y. S. Chen, Y. C. Li, L. Liu, Z. Y. Qian, and Y. Q. Wei, Biomaterials, 34, 1413 (2013).
M. L. Gou, K. Men, H. S. Shi, M. L. Xiang, J. A. Zhang, J. Song, J.L. Long, Y. Wan, F. Luo, X. Zhao, and Z. Y. Qian, Nanoscale, 3, 1558 (2011).
L. D. Hu, Y. H. Jia, F. Niu, Z. Jia, X. Yang, and K. L. Jiao, J. Agric. Food Chem., 60, 7137 (2012).
A. B. Hegge, M. Vukicevic, E. Bruzell, S. Kristensen, and H. H. Tonnesen, Eur. J. Pharm. Biopharm., 83, 95 (2013).
S. Onoue, H. Takahashi, Y. Kawabata, Y. Seto, J. Hatanaka, B. Timmermann, and S. Yamada, J. Pharm. Sci., 99, 1871 (2010).
C. R. Becer, M. I. Gibson, J. Geng, R. Ilyas, R. Wallis, D. A. Mitchell, and D. M. Haddleton, J. Am. Chem. Soc., 132, 15130 (2010).
M. Ahmed and R. Narain, Biomaterials, 32, 5279 (2011).
E. J. Lee, H. S. Kim, and U. S. Shin, Macromol. Res., 24, 429 (2016).
X. Q. Chen, G. D. Zhou, X. J. Peng, and J. Yoon, Chem. Soc. Rev., 41, 4610 (2012).
H. N. Kim, Z. Q. Guo, W. H. Zhu, J. Yoon, and H. Tian, Chem. Soc. Rev., 40, 79 (2011).
Y. Wang, C. Y. Hong, and C. Y. Pan, Biomacromolecules, 13, 2585 (2012).
J. W. Lu, W. D. Zhang, L. Yuan, W. J. Ma, X. Li, W. Lu, Y. Zhao, and G. J. Chen, Macromol. Biosci., 14, 340 (2014).
L. Albertin, M. Stenzel, C. Barner-Kowollik, L. J. R. Foster, and T. P. Davis, Macromolecules, 37, 7530 (2004).
B. B. Aggarwal, A. Kumar, and A. C. Bharti, Anticancer Res., 23, 363 (2003).
K. K. Gupta, S. S. Bharne, K. Rathinasamy, N. R. Naik, and D. Panda, FEBS J., 273, 5320 (2006).
K. I. Priyadarsini, Curr. Pharm. Des., 19, 2093 (2013).
D. Morin, S. Barthelemy, R. Zini, S. Labidalle, and J. P. Tillement, FEBS Lett., 495, 131 (2001).
B. C. Dickinson, C. Huynh, and C. J. Chang, J. Am. Chem. Soc., 132, 5906 (2010).
E. W. Miller, O. Tulyanthan, E. Y. Isacoff, and C. J. Chang, Nat. Chem. Biol., 3, 263 (2007).
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Zhang, H., Ren, T., Yu, M. et al. Synthesis and characterization of curcumin-incorporated glycopolymers with enhanced water solubility and reduced cytotoxicity. Macromol. Res. 24, 655–662 (2016). https://doi.org/10.1007/s13233-016-4095-4
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DOI: https://doi.org/10.1007/s13233-016-4095-4