H6[P2Mo18O62]的钒取代多金属氧酸盐对小鼠黑色素瘤细胞B16黑色素生成的调控及其机制研究

doi:10.6023/A21110528

摘要/Abstract

合成了五种多金属氧酸盐. 以B16小鼠黑色素瘤细胞为模型, 用噻唑蓝(MTT)法检测细胞存活率, 酶标法测定抗氧化活性和内黑色素含量及酪氨酸酶活性, 最后用分子对接模拟多金属氧酸盐和酪氨酸酶结合的机制. 研究结果表明, 两种磷钼酸(H₇[P₂Mo₁₇VO₆₂]和H₈[P₂Mo₁₆V₂O₆₂])是高效的黑色素生成抑制剂, 在200 μmol/L的浓度下对黑色素合成的抑制率为74.40%和75.14%, 对细胞内酪氨酸酶活性的抑制率为35.71%和40.00%, 随着钒原子取代个数的增加, 两种抑制活性均逐渐降低. H₇[P₂Mo₁₇VO₆₂]和H₈[P₂Mo₁₆V₂O₆₂]对细胞没有毒性. 两种多酸都有较好的1,1-二苯基-2-三硝基苯肼(DPPH)清除能力, IC₅₀分别为1.683和2.800 mg/mL. 分子对接分数低于–146 kJ/mol. 综上所述, H₇[P₂Mo₁₇VO₆₂]和H₈[P₂Mo₁₆V₂O₆₂]能抑制B16细胞黑色素的生成, 其机制与抑制酪氨酸酶的活性有关.

关键词: 多金属氧酸盐, B16黑色素瘤细胞, 黑色素, 分子对接, 酪氨酸酶

Melanin is the main cause of pigmentation in human skin, eyes and hair. In order to study the effects of polyoxometalates on the tyrosinase activity and melanin content of B16 mouse melanocytes, five polyoxometalates with Dawson structure with different vanadium substitutions were synthesized. Taking B16 mouse melanoma cells as a model, which was divided into blank group, control group and polyoxometalates experiment group (12.5, 25, 50, 100, 200 μmol/L), the cell viability was detected by thiazolyl blue (MTT) method, and the diphenyl picryl hydrazinyl (DPPH) free radical scavenging ability and the melanin content and tyrosinase activity in B16 melanoma cells were determined by enzyme labeling method. Finally, molecular docking was used to simulate the binding mechanism of polyoxometalate and tyrosinase. The results of the study showed that two phosphomolybdic acids (H₇[P₂Mo₁₇VO₆₂] and H₈[P₂Mo₁₆V₂O₆₂]) are highly effective melanin production inhibitors, and the best inhibitory rates of melanin synthesis at a concentration of 200 μmol/L are 74.40% and 75.14%, respectively, which have an effect on the cell. The inhibitory rates of tyrosinase activity were 35.71% and 40.00%. With the increase of the number of vanadium atoms substituted, the two inhibitory activities gradually decreased. MTT reduction experiments show that H₇[P₂Mo₁₇VO₆₂] and H₈[P₂Mo₁₆V₂O₆₂] are not toxic to cells, and the cell viability is greater than 80%. Both polyoxometalates (POMs) have strong DPPH scavenging ability, with IC₅₀ of 1.683 and 2.800 mg/mL, respectively. Molecular docking simulation proved that all five polyoxometalates can form stable complexes with tyrosinase, and the main force of the combination are non-covalent bonds such as van der Waals forces and hydrogen bonds. In addition, the docking score is less than –146 kJ/mol. Based on the above research, H₇[P₂Mo₁₇VO₆₂] and H₈[P₂Mo₁₆V₂O₆₂] can effectively inhibit the production of melanin in B16 mouse melanoma cells. The mechanism is related to the inhibition of tyrosinase activity. We believe that they are promising candidates for the development of safe cosmetics.

Key words: polyoxometalates, B16 melanocytes, melanin, molecular docking, tyrosinase

引用此文

陈祥松, 帅蝶, 姜泽东, 杨晗, 罗丹, 倪辉, 王力, 陈丙年. H₆[P₂Mo₁₈O₆₂]的钒取代多金属氧酸盐对小鼠黑色素瘤细胞B16黑色素生成的调控及其机制研究[J]. 化学学报, 2022, 80(2): 116-125.

Xiangsong Chen, Die Shuai, Zedong Jiang, Han Yang, Dan Luo, Hui Ni, Li Wang, Bingnian Chen. Study on the Regulation and Mechanism of the Vanadium Substituted Polyoxometalates of H₆[P₂Mo₁₈O₆₂] on Melanogenesis of Mouse Melanoma Cell B16[J]. Acta Chimica Sinica, 2022, 80(2): 116-125.

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图/表 9

图1. (a) P2Mo17V, P2Mo16V2, P2Mo15V3, P2Mo14V4 和 P2Mo13V5 的紫外可见光谱; (b)傅里叶红外光谱; (c)X射线粉末衍射; (d) 核磁共振磷谱; (e) Dawson结构的球棍示意图

Figure 1. (a) UV spectra of P2Mo17V, P2Mo16V2, P2Mo15V3, P2Mo14V4 and P2Mo13V5; (b) IR spectra; (c) XRD spectra; (d) 31P-NMR spectra; (e) Schematic diagram of the Dawson structure ball and stick

图2. P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d), P2Mo13V5 (e)对B16小鼠黑色素瘤细胞的细胞毒性. 值表示为控制组的百分比. 结果通过方差分析(ANOVA)和Tukey检验进行比较. 数据为平均值±标准偏差(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f) B16细胞经过五种钒取代的Dawson型磷钼酸处理72 h后的细胞存活率

Figure 2. The relative cell viability in each experimental group after 72 h of P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d) and P2Mo13V5 (e) treatment. Values are represented as % of control value. The results were compared by analysis of variance (ANOVA) followed by Tukey's test. Data are mean±standard deviation(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f) The viability of B16 cells were treated with five vanadium substituted Dawson phosphomolybdic acids for 72 h

多酸	IC₅₀/(µmol•L^–1)
P₂Mo₁₇V	>200
P₂Mo₁₆V₂	>200
P₂Mo₁₅V₃	>200
P₂Mo₁₄V₄	>200
P₂Mo₁₃V₅	123.8±17.8

表1. 五种化合物对B16黑色素瘤细胞增殖的影响

Table 1. Effects of five compounds on B16 melanoma cells viability

图3. P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d), P2Mo13V5 (e)对B16小鼠黑色素瘤细胞内黑色素含量的影响. 值表示为控制组的百分比. 结果通过方差分析(ANOVA)和Tukey检验进行比较. 数据为平均值±标准偏差(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f)多酸对B16细胞内黑色素含量影响的热图. 颜色的深浅表示该值的大小, 越绿表示抑制效果越好, 越红代表抑制效果越差. 横轴代表不同多酸(A=P2Mo17V, B=P2Mo16V2, C=P2Mo15V3, D=P2Mo14V4, E=P2Mo13V5), 纵轴代表不同浓度, 单位为μmol/L

Figure 3. The effects of P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d), P2Mo13V5 (e) on melanin content in B16 mouse melanoma cells. Values are represented as % of control value. The results were compared by analysis of variance (ANOVA) followed by Tukey’s test. Data are mean±standard deviation(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f) Heatmap of effects of POMs on melanin content in B16 cell. The degree of color depth represents the magnitude of the value. The more green represents the better suppression effect and the redder represents the worse suppression effect. The horizontal axis represents different POMs (A=P2Mo17V, B=P2Mo16V2, C=P2Mo15V3, D=P2Mo14V4, E=P2Mo13V5), and the vertical axis represents different concentrations in μmol/L

图4. P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d), P2Mo13V5 (e)对B16小鼠黑色素瘤细胞内酪氨酸酶活性的影响. 值表示为控制组的百分比. 结果通过方差分析(ANOVA)和Tukey检验进行比较. 数据为平均值±标准偏差(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f)多酸对B16细胞内酪氨酸酶活性影响的热图. 颜色的深浅表示该值的大小, 越绿表示抑制效果越好, 越红代表抑制效果越差. 横轴代表不同多酸(A=P2Mo17V, B=P2Mo16V2, C=P2Mo15V3, D=P2Mo14V4, E=P2Mo13V5), 纵轴代表不同浓度, 单位为μmol/L

Figure 4. The effects of P2Mo17V (a), P2Mo16V2 (b), P2Mo15V3 (c), P2Mo14V4 (d), P2Mo13V5 (e) on tyrosinase activity in B16 mouse melanoma cells. Values are represented as % of control value. The results were compared by analysis of variance (ANOVA) followed by Tukey’s test. Data are mean±standard deviation(*p<0.05, **p<0.01, ***p<0.001, ****p<0.0001). (f) Heatmap of effects of POMs on tyrosinase activity in B16 cell. The degree of color depth represents the magnitude of the value. The more green represents the better suppression effect and the redder represents the worse suppression effect. The horizontal axis represents different POMs (A=P2Mo17V, B=P2Mo16V2, C=P2Mo15V3, D=P2Mo14V4, E=P2Mo13V5), and the vertical axis represents different concentrations in μmol/L

图5. 不同钒取代个数的Dawson型磷钼酸对DPPH的清除作用

Figure 5. DPPH scavenging activities of Dawson phosphomolybdic acid with different number of vanadium substitution

图6. 酪氨酸酶(PDB ID:2Y9W)和P2Mo17V之间的对接相互作用. (a)目标蛋白活性区域与多酸相互作用的所有氨基酸的2D平面图. 多酸与受体蛋白残基His263、Phe292、His61(绿色短划线)之间存在三个π-π键相互作用. (b)多酸进入酪氨酸酶的活性袋, 完成与酪氨酸酶的对接. 其中, 红色氨基酸残基标签表示与配体存在氢键, 粉红色虚线表示与铜离子之间的金属连接. (c)P2Mo17V和酪氨酸酶活性部位关键氨基酸之间相互作用的示意图

Figure 6. Docking interactions between tyrosinase (PDB ID: 2Y9W) and P2Mo17V. (a) 2D plan view of all amino acids interacting with POM in the active region of the target protein. There are three π-π interactions between the POM and the receptor protein residues His263, Phe292, His61(Green dash). (b) The POM enters the active pocket of tyrosinase to complete the docking with tyrosinase. Among them, the red amino acid residue label indicates that there is a hydrogen bond with the ligand, and the pink dash line indicates the metal connection with the copper. (c) Illustration of interaction between P2Mo17V and key amino acid of tyrosinase active site

化合物	氢键和金属键相关氨基酸	氢键数量	大π键	对接分数(kJ/mol)
P₂Mo₁₇V	His61, His94, His263, Asn259, Asn260	5	His61, His263, Phe292	–191
P₂Mo₁₆V₂	His61, His9, His263, Asn244, Asn260	5	His61, His263, Phe292	–183
P₂Mo₁₅V₃	His6, His94, His263, Asn259, Asn260	6	无	–158
P₂Mo₁₄V₄	His85, His259, Asn260	3	His263	–167
P₂Mo₁₃V₅	His61, His94, His244, His259	6	His263	–146

表2. 五种化合物与酪氨酸酶的对接效应

Table 2. Docking effects of five compounds with tyrosinase

化合物	NH₄VO₃		NaH₂PO₄		Na₂MoO₄•2H₂O		pH
化合物	体积/mL	用量/mol	体积/mL	用量/mol	体积/mL	用量/mol	pH
P₂Mo₁₇V	100	0.0100	25	0.02	75	0.170	3.6
P₂Mo₁₆V₂	100	0.0200	25	0.02	100	0.160	3.8
P₂Mo₁₅V₃	150	0.0300	25	0.02	100	0.150	4.0
P₂Mo₁₄V₄	150	0.0400	25	0.02	75	0.140	4.2
P₂Mo₁₃V₅	120	0.0375	15	0.01	40	0.065	4.4

表3. 五种钒取代Dawson型多酸的合成条件

Table 3. Synthesis conditions of five vanadium-substituted Dawson-type polyoxometalates.

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H₆[P₂Mo₁₈O₆₂]的钒取代多金属氧酸盐对小鼠黑色素瘤细胞B16黑色素生成的调控及其机制研究

Study on the Regulation and Mechanism of the Vanadium Substituted Polyoxometalates of H₆[P₂Mo₁₈O₆₂] on Melanogenesis of Mouse Melanoma Cell B16

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