Amino-modified carbon dots as a functional platform for drug delivery: Load-release mechanism and cytotoxicity

Nana Shi; Kaiyue Sun; Zedi Zhang; Juan Zhao; Lina Geng; Yuhua Lei

Journal of Industrial and Engineering Chemistry, Vol.101, 372-378, September, 2021

DOI10.1016/j.jiec.2021.05.046 Export Citation

Amino-modified carbon dots as a functional platform for drug delivery: Load-release mechanism and cytotoxicity

Nana Shi, Kaiyue Sun, Zedi Zhang, Juan Zhao¹, Lina Geng^†, and Yuhua Lei^{1, †}

Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024, PR China
¹College of Basic Medicine, Hebei Medical University, Shijiazhuang 050017, PR China

E-mail:,

Carbon dot (CDs) were prepared for carrying DOX (Doxorubicin) or FAC (Ferric ammonium citrate), and the loading mechanism and release kinetics of CDs-drugs were studied. CDs were prepared using peony pollen and urea, and characterized by TEM, XRD, 13C NMR, XPS, UV, FT-IR, DLS and zeta potential. The obtained CDs were rich of -NH2 group on the surface, amorphous phase, spherical morphology with the diameter about 5 nm, and had a blue fluorescence with the quantum yield (QY) of 12%. Iron disorders can cause cancer or anemia. DOX is used for treating cancer, but has severe side effects. FAC is an iron supplement agent, but had low bioavailability. CDs carried DOX (or FAC) through -N=C. (or -CONH-) bond, had high loading efficiency for DOX (37.2%) and FAC (54.0%) by optimizing mass ratios of mCDs to mdrug and reacted overnight. Cellular experiments showed that CDs-drugs had lower cytotoxicity than free drugs and CDs co-located with the drug. In vitro release indicated that CDs-DOX had pH-targeted property and CDs-FAC could be absorbed easily. CDs-drug release belonged to Weibull model, and release mechanism was determined by the bonding way between CDs and drug. CDs had potential applications in delivery drugs with -C=O or -COOH group.

Keywords:Carbon dots;Iron metabolism;Oxidative stress;Drug release

[References]

Xu XY, Ray R, Gu YL, Ploehn HJ, Gearheart L, Raker K, Scrivens WA, J. Am. Chem. Soc., 26, 12736 (2004)
Sun YP, Zhou B, Lin Y, Wang W, Fernando KAS, Pathak P, Meziani MJ, Harruff BA, Wang X, Wang HF, Luo PJG, Yang H, Kose ME, Chen BL, Veca LM, Xie SY, J. Am. Chem. Soc., 128(24), 7756 (2006)
Jaleel JA, Pramod K, J. Control. Release, 269, 302 (2018)
Myint AA, Rhim WK, Nam JM, Kim JH, Lee YW, J. Ind. Eng. Chem., 66, 387 (2018)
Zhou L, Liu J, Zhang X, Liu R, Huang H, Liu Y, Kang Z, Nanoscale, 6, 5831 (2014)
Naghdi T, Atashi M, Golmohammadi H, Saeedi I, Alanezhad M, J. Ind. Eng. Chem., 52, 162 (2017)
Du SM, Shang BB, Zhang XR, Feng F, Zhang SH, Qi BP, Bull. Korean Chem. Soc., 41, 948 (2020)
Park JH, Yu K, Min JY, Chung YH, Yoon JY, Bull. Korean Chem. Soc. (2021).
Wang Q, Huang X, Long Y, Wang X, Zhang H, Zhu R, Liang L, Teng P, Zheng H, Carbon, 59, 192 (2013)
Han J, Na K, J. Ind. Eng. Chem., 80, 722 (2019)
Jia X, Pei M, Zhao X, Tian K, Zhou T, Liu P, ACS Biomater. Sci. Eng., 2, 1641 (2016)
Zhang Z, Lei Y, Yang X, Shi N, Geng L, Wang S, Zhang J, Shi S, J. Mater. Chem. B, 7, 2130 (2019)
Zhang H, Zhabyeyev P, Wang S, Oudit GY, Biochim. Biophys. Acta, Mol. Basis Dis., 1865, 1925 (2019)
Li SH, Amat D, Peng ZL, Vanni S, Raskin S, De Angulo G, Othman AM, Graham RM, Leblanc RM, Nanoscale, 8, 16662 (2016)
Zhang R, Yuan L, Sun K, Wang S, Geng L, Zhang J, Acta Phys. -Chim. Sin., 36(6), 190509 (2020)
Yuan L, Geng L, Ge L, Yu P, Duan X, Chen J, Chang Y, Int. J. Pharm., 454, 82 (2013)
Guo X, Zheng H, Guo Y, Wang Y, Anderson GJ, Ci Y, Yu P, Geng L, Chang YZ, J. Nanobiotechnology, 15, 42 (2017)
Kwak M, Jung I, Kang YG, Lee DK, Park S, Nanoscale, 10, 18690 (2018)
Liu D, Bi YG, Adv. Powder Technol., 30(10), 2169 (2019)
Rezk AI, Obiweluozor FO, Choukrani G, Park CH, Kim CS, Int. J. Biol. Macromol., 141, 388 (2019)
Jain A, Jain SK, Chem. Phys. Lipids (2016).
Kregar ML, et al., International Journal of Pharmaceutics, 485, 202 (2015).
Qu S, Wang X, Lu Q, Liu X, Wang L, Angew. Chem.-Int. Edit., 51, 12215 (2012)
Zhang M, Wang W, Zhou N, Yuan P, Su Y, Shao M, Chi C, Pan F, Carbon, 118, 752 (2017)
Fatouros DG, Antimisiaris SG, J. Colloid Interface Sci., 251(2), 271 (2002)
Xu ZQ, Yang QQ, Lan JY, Zhang JQ, Peng W, Jin JC, Jiang FL, Liu Y, J. Hazard. Mater., 301, 242 (2016)
Gong X, Zhang Q, Gao Y, Shuang S, Choi MM, Dong C, ACS Appl. Mater. Interfaces, 8, 11288 (2016)
Zeng YW, Ma DK, Wang W, Chen JJ, Zhou L, Zheng YZ, Yu K, Huang SM, Appl. Surf. Sci., 342, 136 (2015)
Reddy MJ, Ryu SH, Shanmugharaj AM, Nanoscale, 8, 471 (2016)
Jia X, Li J, Wang E, Nanoscale, 4, 5572 (2012)
An J, Guo Q, Zhang P, Sinclair A, Zhao Y, Zhang X, Wu K, Sun F, Hung HC, Li C, Jiang S, Nanoscale, 8, 9318 (2016)
Shen HL, Yang SP, Hong LW, Lin LQ, Wang KJ, Cai XH, Lv GR, Ultrasound Med. Biol., 40, 1998 (2014)
Xie W, Zhou L, Xu J, Guo Q, Jiang F, Acta Phys.- Chim. Sin., 36(6), 190505 (2020)
Xing Z, Guo Z, Zhang Y, Liu J, Wang Y, Bai G, Actc Phys. - Chim. Sin., 36(6), 190600 (2020)

[1] Xu XY, Ray R, Gu YL, Ploehn HJ, Gearheart L, Raker K, Scrivens WA, J. Am. Chem. Soc., 26, 12736 (2004)

[2] Sun YP, Zhou B, Lin Y, Wang W, Fernando KAS, Pathak P, Meziani MJ, Harruff BA, Wang X, Wang HF, Luo PJG, Yang H, Kose ME, Chen BL, Veca LM, Xie SY, J. Am. Chem. Soc., 128(24), 7756 (2006)

[3] Jaleel JA, Pramod K, J. Control. Release, 269, 302 (2018)

[4] Myint AA, Rhim WK, Nam JM, Kim JH, Lee YW, J. Ind. Eng. Chem., 66, 387 (2018)

[5] Zhou L, Liu J, Zhang X, Liu R, Huang H, Liu Y, Kang Z, Nanoscale, 6, 5831 (2014)

[6] Naghdi T, Atashi M, Golmohammadi H, Saeedi I, Alanezhad M, J. Ind. Eng. Chem., 52, 162 (2017)

[7] Du SM, Shang BB, Zhang XR, Feng F, Zhang SH, Qi BP, Bull. Korean Chem. Soc., 41, 948 (2020)

[8] Park JH, Yu K, Min JY, Chung YH, Yoon JY, Bull. Korean Chem. Soc. (2021).

[9] Wang Q, Huang X, Long Y, Wang X, Zhang H, Zhu R, Liang L, Teng P, Zheng H, Carbon, 59, 192 (2013)

[10] Han J, Na K, J. Ind. Eng. Chem., 80, 722 (2019)

[11] Jia X, Pei M, Zhao X, Tian K, Zhou T, Liu P, ACS Biomater. Sci. Eng., 2, 1641 (2016)

[12] Zhang Z, Lei Y, Yang X, Shi N, Geng L, Wang S, Zhang J, Shi S, J. Mater. Chem. B, 7, 2130 (2019)

[13] Zhang H, Zhabyeyev P, Wang S, Oudit GY, Biochim. Biophys. Acta, Mol. Basis Dis., 1865, 1925 (2019)

[14] Li SH, Amat D, Peng ZL, Vanni S, Raskin S, De Angulo G, Othman AM, Graham RM, Leblanc RM, Nanoscale, 8, 16662 (2016)

[15] Zhang R, Yuan L, Sun K, Wang S, Geng L, Zhang J, Acta Phys. -Chim. Sin., 36(6), 190509 (2020)

[16] Yuan L, Geng L, Ge L, Yu P, Duan X, Chen J, Chang Y, Int. J. Pharm., 454, 82 (2013)

[17] Guo X, Zheng H, Guo Y, Wang Y, Anderson GJ, Ci Y, Yu P, Geng L, Chang YZ, J. Nanobiotechnology, 15, 42 (2017)

[18] Kwak M, Jung I, Kang YG, Lee DK, Park S, Nanoscale, 10, 18690 (2018)

[19] Liu D, Bi YG, Adv. Powder Technol., 30(10), 2169 (2019)

[20] Rezk AI, Obiweluozor FO, Choukrani G, Park CH, Kim CS, Int. J. Biol. Macromol., 141, 388 (2019)

[21] Jain A, Jain SK, Chem. Phys. Lipids (2016).

[22] Kregar ML, et al., International Journal of Pharmaceutics, 485, 202 (2015).

[23] Qu S, Wang X, Lu Q, Liu X, Wang L, Angew. Chem.-Int. Edit., 51, 12215 (2012)

[24] Zhang M, Wang W, Zhou N, Yuan P, Su Y, Shao M, Chi C, Pan F, Carbon, 118, 752 (2017)

[25] Fatouros DG, Antimisiaris SG, J. Colloid Interface Sci., 251(2), 271 (2002)

[26] Xu ZQ, Yang QQ, Lan JY, Zhang JQ, Peng W, Jin JC, Jiang FL, Liu Y, J. Hazard. Mater., 301, 242 (2016)

[27] Gong X, Zhang Q, Gao Y, Shuang S, Choi MM, Dong C, ACS Appl. Mater. Interfaces, 8, 11288 (2016)

[28] Zeng YW, Ma DK, Wang W, Chen JJ, Zhou L, Zheng YZ, Yu K, Huang SM, Appl. Surf. Sci., 342, 136 (2015)

[29] Reddy MJ, Ryu SH, Shanmugharaj AM, Nanoscale, 8, 471 (2016)

[30] Jia X, Li J, Wang E, Nanoscale, 4, 5572 (2012)

[31] An J, Guo Q, Zhang P, Sinclair A, Zhao Y, Zhang X, Wu K, Sun F, Hung HC, Li C, Jiang S, Nanoscale, 8, 9318 (2016)

[32] Shen HL, Yang SP, Hong LW, Lin LQ, Wang KJ, Cai XH, Lv GR, Ultrasound Med. Biol., 40, 1998 (2014)

[33] Xie W, Zhou L, Xu J, Guo Q, Jiang F, Acta Phys.- Chim. Sin., 36(6), 190505 (2020)

[34] Xing Z, Guo Z, Zhang Y, Liu J, Wang Y, Bai G, Actc Phys. - Chim. Sin., 36(6), 190600 (2020)