Influence of plasma-activated compounds on melanogenesis and tyrosinase activity
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1 Supporting file Influence of plasma-activated compounds on melanogenesis and tyrosinase activity Anser Ali 1,2, Zaman Ashraf 3,4, Naresh Kumar 1,2, Muhammad Rafiq 3, Farukh Jabeen 6,7, Jihoon Park 5, Ki Hong Choi 5, SeungHyun Lee 1,2, Sung-Yum Seo 3, Eun Ha Choi 1,2,5 * and Pankaj Attri 2,5,8 * 1 Department of Plasma-Bio Display, 2 Plasma Bioscience Research Center, Kwangwoon University, 20 Kwangwoon-gil, Nowon-gu, Seoul , Republic of Korea 3 Department of Biology, College of Natural Sciences, Kongju National University, Gongju , Republic of Korea 4 Department of Chemistry, Allama Iqbal pen University, Islamabad 44000, Pakistan 5 Department of Electrical and Biological Physics, Kwangwoon University, 20 Kwangwoon-gil, Nowon-gu, Seoul , Republic of Korea 6 Florida Center of Heterocyclic Compounds, University of Florida, Gainesville, Fl, 32601, USA 7 Center for Computationally Assisted Science and Technology, North Dakota State University, Fargo, ND, 58102, USA 8 Graduate School of Information Science and Electrical Engineering, Kyushu University Fukuoka , Japan Figure S1: ptical emission spectrum detected from atmospheric pressure plasma jet (APPJ) using HR4000 spectrometer. The x-axix of detected spectrum is broken as (a) nm, (b) nm and (c) nm wavelengths for more details and clarity of spectrum. Figure S2: NMR before and after the plasma treatment to (a) 4b and (b) 6a compounds. Figure S3: 2D interactions of eugenol derivatives. 2D interactions of as-synthesized eugenol derivatives (a) 4a, (b) 4b, (c) 4c, (d) 4d, (e) 4e, (f) 6a, (g) 6b, and (h) a reference compound kojic acid are given. However, the 2D image (i) shows plasma treated 4b and image (j) shows plasma treated 6a interactions. (color and pattern details are given in the legend). Figure S4: Cell viability measurement. The murine melanoma (B16F10), human skin keratinocyte (HaCaT), and murine skin fibroblast (L929) cells were incubated with different concentrations of (a) 4a, (b) 4c, (c) 4d, (d) 4e, and (e) 6b ED compounds and cell viability was accessed by MTT assay. The data were expressed as a percentage of the control (normalized to
2 100%) from three independent experiments with mean ± standard deviation and were analyzed using Student s t-tests, *p<0.05, **p< Figure S5: Cell morphology. Melanoma cells were incubated with various concentrations of 4b (a1) 0 µg/ml (control), (a2) 14 µg/ml, (a3) 21 µg/ml, (a4) 28 µg/ml, (a5) 35 µg/ml, (a6) 42 µg/ml and 6a (b1) 0 µg/ml (control), (b2) 14 µg/ml, (b3) 21 µg/ml, (b4) 28 µg/ml, (b5) 35 µg/ml, (b6) 42 µg/ml for 24 hours and images with a 100-µm scale bar were taken by inverted fluorescent microscope. Figure S6: Intracellular melanin measurement. B16F10 cells were incubated with various concentrations of (a) 4a, (b) 4c, (c) 4d, (d) 4e, and (e) 6b and intracellular melanin was detected. All data were expressed as a percentage of the control (normalized to 100%) from three independent experiments with mean ± standard deviation and were analyzed using Student s t- tests, *p<0.05. Figure S7. Images of melanoma B16F10 cell pallets. B16F10 cells were incubated with indicated concentrations of 4b and 6a for 24 hr and then centrifuged to photograph the cell pellet. The cells grown with media only are shown as the control, while the cells grown with α-msh and Kojic acid in media are shown as positive and negative controls, respectively. Table S1: Representation of binding affinity with specific interactions of as-synthesized eugenol derivatives (a) 4a, 4b, (b) 4c, 4d, (c) 4e, 6a, (d) 6b, kojic acid (a reference compound) is given. However, table (e) shows interactions for plasma treated 4b and plasma treated 6a eugenol derivatives.
3 Codes 4a Binding Energy (kcal/mol) London S dg H-Bonding Interacting residues Distance (Å) π-h π-π interaction interaction Arg268-H Val283 CH 3 Hydrophobic Interactions Val283 Phe264 Val248 Polar interaction His244 His263 Glu322 Arg2608 Cu-ligand Interaction 4b H 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl 3-hydroxybenzoate (4a) His263 H 3.9 His85 - CH 3 CH 2 Phe264 Val283 Val248 Asn260 His244 His85 Asn81 Glu322 CU400-C= 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl 4-hydroxybenzoate (4b) CH 2 Table S1(a)
4 Codes Binding Energy (kcal/mol) London S dg H-Bonding Interacting residues Distance (Å) π-h interaction π-π interaction Hydrophobic Interactions Polar interaction Cu-ligand Interaction 4c H CH 3 Val283 Phe264 Val248 His244 Glu322 Asn81 Asn260 H 4d 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl 2,4-dihydroxybenzoate (4c) H H CH 3 His263 CH 2 CH 2 Val283 Phe264 Val248 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl 3,4-dihydroxybenzoate (4d) His263 His85 His244 Glu322 Asn260 Table S1(b)
5 Codes Binding Energy (kcal/mol) S London dg Interacting residues H-Bonding Distance (Å) π-h interaction π-π interaction Hydrophobic Interactions Polar interaction Cu-ligand Interaction Val283 Ala264 Val248 Phe264 His85 His244 Asn260 4e CH 3 H 6a H 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl 3,5-dihydroxybenzoate (4e) Glu322-H 3.81 H His85 Val283 CH 2 His263 CH 3 Val248 Phe264 Val283 His85 His244 Glu322 Asn260 His263 CU-400- C= CH 2 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate (6a) Table S1(c)
6 Codes Binding Energy (kcal/mol) London S dg Interacting residues H-Bonding Distance (Å) π-h interaction π-π interaction Hydrophobic Interactions Polar interaction Cu-ligand Interaction His85 - Val283 Phe264 Val248 His85 Glu322 Asn260 CH 3 6b Cl Kojic acid CH 2 2-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-2-oxoethyl(2E)-3-(4-chloroyphenyl)prop-2-enoate (6b) His85 Val His Asn260 His263 Cu-C= Cu--H Kojic acid Table S1(d)
7 Codes Plasma treated 4b Binding Energy (kcal/mol) London S dg H-Bonding Interacting residues Ala-246 Glu-322 Ala-323 His-263 Distance (Å) π-h interaction His-85 Val-283 π-π Hydrophobic interaction Interactions CH 2 -H - Phe264 Val248 Met257 Polar interaction His85 His244 His263 Glu322 Asn260 His81 Cu-ligand Interaction Cu-C= H Plasma treated 6a Proposed structure for plasma treated 4b His-85 H CH 2 H - Val248 Phe264 Val283 Thr261 His244 Glu322 Asn260 His85 His263 Asn-85 Cu-C= CH 3 Proposed structure for plasma treated 6a Table S1(e)
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