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

doi:10.6023/A21110528

Abstract

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

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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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Fig. & Tab. 9

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

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

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

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

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

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

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

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

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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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