Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles†

doi:10.7503/cjcu20150591

Abstract

Abstract:

New pH-responsive pectin derivatives were designed and synthesized by esterification. The architectures of the polymers were confirmed by Fourier transform infrared(FTIR) spectrophoto meter and Elemental analyses(EA). The prepared micelles properties were determined by UV-Vis spectra and transmission electron microscope(TEM). The cytotoxicity of Curcumin/His-Pectin colloidal particles was assessed using the cell counting kit-8 assay. The His-Pectin colloidal particles exhibited an irregular spherical shape from TEM photographs. Moreover, curcumin can be efficiently encapsulated in His-Pectin colloidal particles. The mean diameter of the curcumin colloidal particles was about 200 nm with narrow size distribution. The cytotoxic assays of Curcumin/His-Pectin colloidal particles demonstrated high inhibitory effect on HepG2 cell growth compared to the free curcumin. It was concluded that His-Pectin colloidal particles can efficiently encapsulate curcumin in vitro and promote the inhibition of HepG2 cell growth in vitro.

Key words: pH-Responsive, Colloidal particles, Drug delivery, Growth inhibition of tumor cells, Amino acid functionalized, Pectin derivatives, Curcumin

CLC Number:

O636.1⁺3

TrendMD:

YANG Zechuan, LI Fan, HUANG Qingrong, ZHANG Guo, SHI Tongfei. Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles^†[J]. Chem. J. Chinese Universities, 2016, 37(2): 381.

Figures/Tables 11

Scheme 1 Synthetic routes of His-Pectin colloidal particles

Fig.1 FTIR spectra of Pectin(a) and His-Pectin(b)

Table 1 Characterization of Pectin and His-Pectin by elemental analyses

Sample	N(mass fraction, %)	n(Glucose unit):n(Boc-Histidine)	DS(%)
Pectin	0.20
His_0.5-Pectin	2.58	1:0.5	13.3
His-Pectin	5.00	1:1	30.6

Fig.2 Effect of pH on the solubility of Pectin(a) and His-Pectin colloidal particles(b) in water(3 mg/mL)

Fig.3 UV-Vis spectra of His-Pectin(a), Curcumin(b) and mixture of His-Pectin and Curcumin(c)

Fig.4 TEM images of His-Pectin(A) and Curcumin/His-Pectin colloidal particles(B—D) m(Curcumin):m(His-Pectin): (B) 1:20; (C) 1:10; (D) 1:5.

Table 2 Characterization of the size and distribution of the colloidal particles at 37 ℃(n=3)

Polymer	Size/nm	PDI
His_0.5-Pectin	285	0.21
His-Pectin	131	0.17
m(Curcumin):m(His_0.5-Pectin)=1:20	218	0.12
m(Curcumin):m(His-Pectin)=1:20	115	0.14
m(Curcumin):m(His-Pectin)=1:10	157	0.11
m(Curcumin):m(His-Pectin)=1:5	233	0.13

Table 3 LE and LC of Curcumin/His-Pectin colloidal particles

Sample	LE(%)	LC(%)
m(Curcumin):m(His_0.5-Pectin)=1:20	86.9	4.2
m(Curcumin):m(His-Pectin)=1:20	86.2	4.2
m(Curcumin):m(His-Pectin)=1:10	78.3	7.3
m(Curcumin):m(His-Pectin)=1:5	69.6	12.2

Fig.5 The in vitro Curcumin release profiles for Curcumin/His-Pectin [m(Curcumin):m(His-Pectin)=1:20] colloidal particles with different pH value

Fig.6 Cytotoxicity of His-Pectin colloidal particles in HepG2 cells Mean±standard derivation(n=4).

Fig.7 Effect of Curcumin/His-Pectin colloidal particles(a), Curcumin(b) and His-Pectin(c) on growth inhibition in HepG2 cell

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