Synthesis and Biological Activities of o-Vanillin-histidine Schiff-base and Its Lanthanum Complex†

doi:10.7503/cjcu20140732

Abstract

Abstract:

Two new compounds, o-vanillin-histidine Schiff-base and its lanthanum(Ⅲ) complex, were synthesized. Element analysis, X-ray diffraction analysis, ultraviolet-visual spectra, infrared spectra, thermogravimetry-differential thermal analysis and chemical analysis were employed to characterize the compositions and structures of o-vanillin-histidine Schiff base and its lanthanum(Ⅲ) complex. The results show that the molecular formula of the o-vanillin-histidine Schiff base and lanthanum(Ⅲ) Schiff base complex are C₁₄H₁₅N₃O₄·H₂O and La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O, respectively. The biological activities of C₁₄H₁₅N₃O₄·H₂O and La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O were studied using biological microcalorimetry. The metabolic thermogenic curves of S. pombe were measured at 301.15 K. Some thermokinetic parameters of growth and metabolism of S. pombe, such as the rate constant(k), generational time(t_G), total thermal effects(Q_total), inhibition ratio(I) and half inhibition concentration(IC₅₀), etc., were calculated. Experimental results show that the k and Q_total values of S. pombe decrease, while t_G and I values of S. pombe increase with the increase of the concentrations of C₁₄H₁₅N₃O₄·H₂O and La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O. The IC₅₀ values for C₁₄H₁₅N₃O₄·H₂O and La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O were found to be 0.2585 and 0.2488 mmol/L, respectively.

Key words: Biological microcalorimetry, Biological activity, o-Vanillin-histidine Schiff-base, Lanthanum(Ⅲ) Schiff-base complex, S. pombe cell

CLC Number:

O614.33
O645

TrendMD:

LI Xu, JIANG Jianhong, HAN Buxing, GU Huiwen, XIE Zhaofeng, CHEN Lan, XIAO Shengxiong, LI Chuanhua, LI Aitao, LI Xia, YAO Feihong, WANG Qun, LI Qiangguo. Synthesis and Biological Activities of o-Vanillin-histidine Schiff-base and Its Lanthanum Complex^†[J]. Chem. J. Chinese Universities, 2015, 36(5): 856.

Figures/Tables 11

Fig.1 IR spectra of the o-vanillin-histidine Schiff-base(a) and Schiff-base lanthanum complex(b)

Fig.2 UV-Vis spectra of the o-vanillin-histidine Schiff-base(a) and Schiff-base lanthanum complex(b)

Fig.3 TG-DSC curves of La(C14H15N3O4)Cl2·3H2O(s)

Fig.4 Molecular structure of the o-vanillin-histidine Schiff-base

Fig.5 3D structure of the lanthanum Schiff-base complex

Fig.6 Power-time curves for the growth and metabolism of S. pombe affected by C14H15N3O4·H2O(A) and La(C14H15N3O4)Cl2·3H2O(B)(A) Concentration of Schiff-base/(mmol·L-1): a. 0; b. 0.1116; c. 0.1435; d. 0.1754; e. 0.2073; f. 0.2392; g. 0.2711; h. 0.3030. (B) Concentration of lanthanum Schiff-base complex/(mmol·L-1): a. 0; b. 0.0918; c. 0.1378; d. 0.1837; e. 0.2066; f. 0.2296; g. 0.2526; h. 0.2755.

Table 1 Thermokinetic parameters of the growth and metabolism of S.pombe affected by C14H15N3O4·H2O and La(C14H15N3O4)Cl2·3H2O at different concentrations at 301.15 K

Compound	c^a/(mmol·L^-1)	k^b /s^-1	$t G c$ /min	$Q total d$ /J	I^e	I $C 50 f$ /(mmol·L^-1)
C₁₄H₁₅N₃O₄·H₂O	0	6.21×10^-5±4.1×1 $0 - 8 g$	186	89.5	0	0.2585
	0.1116	5.61×10^-5±3.0×10^-8	206	87.6	9.66
	0.1435	5.16×10^-5±2.8×10^-8	224	86.2	16.91
	0.1754	4.60×10^-5±2.6×10^-8	251	83.4	25.93
	0.2073	3.87×10^-5±4.7×10^-9	299	77.3	37.68
	0.2392	3.40×10^-5±5.8×10^-8	340	71.8	45.25
	0.2711	2.89×10^-5±7.7×10^-8	390	64.1	53.46
	0.3030	2.39×10^-5±8.8×10^-8	483	53.7	61.51
La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O	0	6.21×10^-5±7.3×10^-8	186	89.2	0	0.2488
	0.0918	5.82×10^-5±5.4×10^-8	198	87.3	6.28
	0.1378	5.11×10^-5±4.1×10^-8	226	85.3	17.71
	0.1837	4.27×10^-5±3.6×10^-8	271	81.0	31.24
	0.2066	3.85×10^-5±4.2×10^-9	300	77.2	38.00
	0.2296	3.53×10^-5±4.6×10^-8	327	73.8	43.16
	0.2526	3.04×10^-5±6.4×10^-8	380	69.6	51.05
	0.2755	2.61×10^-5±7.2×10^-8	443	64.9	57.97

Table 1 Thermokinetic parameters of the growth and metabolism of S.pombe affected by C14H15N3O4·H2O and La(C14H15N3O4)Cl2·3H2O at different concentrations at 301.15 K

Compound	c^a/(mmol·L^-1)	k^b /s^-1	$t G c$ /min	$Q total d$ /J	I^e	I $C 50 f$ /(mmol·L^-1)
C₁₄H₁₅N₃O₄·H₂O	0	6.21×10^-5±4.1×1 $0 - 8 g$	186	89.5	0	0.2585
	0.1116	5.61×10^-5±3.0×10^-8	206	87.6	9.66
	0.1435	5.16×10^-5±2.8×10^-8	224	86.2	16.91
	0.1754	4.60×10^-5±2.6×10^-8	251	83.4	25.93
	0.2073	3.87×10^-5±4.7×10^-9	299	77.3	37.68
	0.2392	3.40×10^-5±5.8×10^-8	340	71.8	45.25
	0.2711	2.89×10^-5±7.7×10^-8	390	64.1	53.46
	0.3030	2.39×10^-5±8.8×10^-8	483	53.7	61.51
La(C₁₄H₁₅N₃O₄)Cl₂·3H₂O	0	6.21×10^-5±7.3×10^-8	186	89.2	0	0.2488
	0.0918	5.82×10^-5±5.4×10^-8	198	87.3	6.28
	0.1378	5.11×10^-5±4.1×10^-8	226	85.3	17.71
	0.1837	4.27×10^-5±3.6×10^-8	271	81.0	31.24
	0.2066	3.85×10^-5±4.2×10^-9	300	77.2	38.00
	0.2296	3.53×10^-5±4.6×10^-8	327	73.8	43.16
	0.2526	3.04×10^-5±6.4×10^-8	380	69.6	51.05
	0.2755	2.61×10^-5±7.2×10^-8	443	64.9	57.97

Fig.7 Rate constant of growth and metabolism of S. pombe with different concentrations of C14H15N3O4·H2O(a) and La(C14H15N3O4)Cl2·3H2O(b)

Fig.8 Generational time of growth and metabolism of S. pombe with different concentrations of C14H15N3O4·H2O(a) and La(C14H15N3O4)Cl2·3H2O(b)

Fig.9 Total thermal effects of growth and meta-bolism of S. pombe with different con-centrations of C14H15N3O4·H2O(a) and La(C14H15N3O4)Cl2·3H2O(b)

Fig.10 Inhibitive rate of growth and metabolism of S. pombe with different concentrations of C14H15N3O4·H2O(a) and La(C14H15N3O4)Cl2·3H2O(b)

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