{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:49:29Z","timestamp":1787028569812,"version":"build-2736575974"},"reference-count":64,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2025,9,13]],"date-time":"2025-09-13T00:00:00Z","timestamp":1757721600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Medical University of Silesia","award":["BNW-1-048\/K\/5\/F"],"award-info":[{"award-number":["BNW-1-048\/K\/5\/F"]}]},{"name":"Medical University of Silesia","award":["BNW-2-039\/K\/4\/F"],"award-info":[{"award-number":["BNW-2-039\/K\/4\/F"]}]},{"name":"Medical University of Silesia","award":["BNW-1-100\/K\/4\/F"],"award-info":[{"award-number":["BNW-1-100\/K\/4\/F"]}]},{"name":"Medical University of Silesia","award":["BNW-1-035\/K\/5\/F"],"award-info":[{"award-number":["BNW-1-035\/K\/5\/F"]}]},{"name":"Medical University of Silesia","award":["BNW-2-016\/N\/5\/F"],"award-info":[{"award-number":["BNW-2-016\/N\/5\/F"]}]},{"name":"Medical University of Silesia","award":["Grant no. 431"],"award-info":[{"award-number":["Grant no. 431"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["BNW-1-048\/K\/5\/F"],"award-info":[{"award-number":["BNW-1-048\/K\/5\/F"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["BNW-2-039\/K\/4\/F"],"award-info":[{"award-number":["BNW-2-039\/K\/4\/F"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["BNW-1-100\/K\/4\/F"],"award-info":[{"award-number":["BNW-1-100\/K\/4\/F"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["BNW-1-035\/K\/5\/F"],"award-info":[{"award-number":["BNW-1-035\/K\/5\/F"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["BNW-2-016\/N\/5\/F"],"award-info":[{"award-number":["BNW-2-016\/N\/5\/F"]}]},{"name":"Wroclaw Centre for Networking and Supercomputing","award":["Grant no. 431"],"award-info":[{"award-number":["Grant no. 431"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Tigecycline is an antibiotic belonging to the glycylcycline group of tetracyclines. Similar to other tetracycline derivatives, tigecycline is used in dermatology because of its bacteriostatic effect. Despite an overall favorable safety profile, tetracyclines are associated with a spectrum of cutaneous adverse effects, notably pigmentary disorders and phototoxic reactions. These dermatologic manifestations are presumed to result from tigecycline\u2019s affinity for melanin biopolymer and its subsequent accumulation within the pigment-containing tissues. This study aimed to assess the impact of tigecycline on human normal skin cell homeostasis varied by melanin content. The study was conducted on HEMn-LP melanocytes and human dermal fibroblasts. The aim was achieved by determining the cell number, cell cycle, mitochondrial potential, and redox homeostasis and determining in silico the possibility of binding tigecycline to melanin biopolymers. In this study, it was shown that the cells more sensitive to tigecycline were HEMn-LP melanocytes. The obtained results showed that tigecycline decreased cell number in a dose-dependent manner. In addition, tigecycline was shown to reduce mitochondrial potential, increase the level of oxidized thiols, and increase ROS content in melanocytes, contributing to oxidative stress. In silico studies have shown that the binding of tigecycline to melanin may play a role in the induction of the toxic effects of tigecycline on the skin.<\/jats:p>","DOI":"10.3390\/ijms26188939","type":"journal-article","created":{"date-parts":[[2025,9,16]],"date-time":"2025-09-16T07:33:02Z","timestamp":1758007982000},"page":"8939","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Effect of Tigecycline on the Homeostasis of Human Epidermal Melanocytes and Fibroblasts"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7892-0462","authenticated-orcid":false,"given":"Zuzanna","family":"Rzepka","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiello\u0144ska 4, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3396-6819","authenticated-orcid":false,"given":"Marta","family":"Karkoszka-Stanowska","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiello\u0144ska 4, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4631-2360","authenticated-orcid":false,"given":"Krzysztof","family":"Marciniec","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiello\u0144ska 4, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Magdalena","family":"Zdybel","sequence":"additional","affiliation":[{"name":"Department of Biophysics, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jedno\u015bci 8, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbara","family":"Pilawa","sequence":"additional","affiliation":[{"name":"Department of Biophysics, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jedno\u015bci 8, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6918-3330","authenticated-orcid":false,"given":"Dorota","family":"Wrze\u015bniok","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiello\u0144ska 4, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,9,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"C539","DOI":"10.1152\/ajpcell.00047.2010","article-title":"Tetracyclines: A pleitropic family of compounds with promising therapeutic properties. Review of the literature","volume":"299","author":"Griffin","year":"2010","journal-title":"Am. J. Physiol. Cell Physiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"44","DOI":"10.2174\/138955712798868977","article-title":"Tetracyclines: Drugs with huge therapeutic potential","volume":"12","author":"Bahrami","year":"2012","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1111\/ajd.12075","article-title":"Non-antibiotic properties of tetracyclines and their clinical application in dermatology","volume":"55","author":"Perret","year":"2014","journal-title":"Australas. J. Dermatol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1111\/idj.12221","article-title":"Non-antibacterial tetracycline formulations: Host-modulators in the treatment of periodontitis and relevant systemic diseases","volume":"66","author":"Golub","year":"2016","journal-title":"Int. Dent. J."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Rusu, A., and Buta, E.L. (2021). The Development of Third-Generation Tetracycline Antibiotics and New Perspectives. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13122085"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Sun, C., Yu, Y., and Hua, X. (2023). Resistance mechanisms of tigecycline in Acinetobacter baumannii. Front. Cell. Infect. Microbiol., 13.","DOI":"10.3389\/fcimb.2023.1141490"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1007\/s10096-020-04121-1","article-title":"Tigecycline antibacterial activity, clinical effectiveness, and mechanisms and epidemiology of resistance: Narrative review","volume":"41","author":"Yaghoubi","year":"2022","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Kounatidis, D., Dalamaga, M., Grivakou, E., Karampela, I., Koufopoulos, P., Dalopoulos, V., Adamidis, N., Mylona, E., Kaziani, A., and Vallianou, N.G. (2024). Third-Generation Tetracyclines: Current Knowledge and Therapeutic Potential. Biomolecules, 14.","DOI":"10.3390\/biom14070783"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"e14978","DOI":"10.1111\/dth.14978","article-title":"Tetracyclines and photosensitive skin reactions: A narrative review","volume":"34","author":"Odorici","year":"2021","journal-title":"Dermatol. Ther."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Karkoszka, M., Rok, J., and Wrze\u015bniok, D. (2024). Melanin Biopolymers in Pharmacology and Medicine-Skin Pigmentation Disorders, Implications for Drug Action, Adverse Effects and Therapy. Pharmaceuticals, 17.","DOI":"10.3390\/ph17040521"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Solano, F. (2020). Photoprotection and skin pigmentation: Melanin-related molecules and some other new agents obtained from natural sources. Molecules, 25.","DOI":"10.3390\/molecules25071537"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1034\/j.1600-0749.13.s8.19.x","article-title":"Chemical analysis of melanins and its application to the study of the regulation of melanogenesis","volume":"13","author":"Ito","year":"2000","journal-title":"Pigment. Cell Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1155","DOI":"10.1152\/physrev.00044.2003","article-title":"Melanin pigmentation in mammalian skin and its hormonal regulation","volume":"84","author":"Slominski","year":"2004","journal-title":"Physiol. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1111\/bcpt.12748","article-title":"Pharmacological properties of melanin and its function in health","volume":"120","author":"ElObeid","year":"2017","journal-title":"Basic Clin. Pharmacol. Toxicol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1111\/j.1600-0749.1993.tb00612.x","article-title":"Role of melanin as a scavenger of active oxygen species","volume":"6","author":"Bustamante","year":"1993","journal-title":"Pigment. Cell Res."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Tanaka, H., Yamashita, Y., Umezawa, K., Hirobe, T., Ito, S., and Wakamatsu, K. (2018). The Pro-Oxidant Activity of Pheomelanin is Significantly Enhanced by UVA Irradiation: Benzothiazole Moieties Are More Reactive than Benzothiazine Moieties. Int. J. Mol. Sci., 19.","DOI":"10.20944\/preprints201809.0091.v1"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"108516","DOI":"10.1016\/j.dyepig.2020.108516","article-title":"Increase of the benzothiazole moiety content of pheomelanin pigment after endogenous free radical inducement","volume":"180","author":"Wakamatsu","year":"2020","journal-title":"Dye. Pigment."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1111\/pcmr.12514","article-title":"Aerobic photoreactivity of synthetic eumelanins and pheomelanins: Generation of singlet oxygen and superoxide anion","volume":"29","author":"Szewczyk","year":"2016","journal-title":"Pigment Cell Melanoma Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1111\/j.1755-148X.2009.00610.x","article-title":"Current challenges in understanding melanogenesis: Bridging chemistry, biological control, morphology, and function","volume":"22","author":"Simon","year":"2009","journal-title":"Pigment Cell Melanoma Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"13201","DOI":"10.1021\/jp804248h","article-title":"Insights into melanosomes and melanin from some interesting spatial and temporal properties","volume":"112","author":"Simon","year":"2008","journal-title":"J. Phys. Chem. B"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Kowalska, J., Rok, J., Rzepka, Z., and Wrze\u015bniok, D. (2021). Drug-Induced Photosensitivity\u2014From Light and Chemistry to Biological Reactions and Clinical Symptoms. Pharmaceuticals, 14.","DOI":"10.3390\/ph14080723"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Thawabteh, A.M., Jibreen, A., Karaman, D., Thawabteh, A., and Karaman, R. (2023). Skin Pigmentation Types, Causes and Treatment\u2014A Review. Molecules, 28.","DOI":"10.20944\/preprints202305.0751.v1"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1512","DOI":"10.1038\/jid.2014.65","article-title":"Melanocytes as instigators and victims of oxidative stress","volume":"134","author":"Denat","year":"2014","journal-title":"J. Investig. Dermatol."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Rok, J., Rzepka, Z., Maszczyk, M., Beberok, A., and Wrze\u015bniok, D. (2021). Minocycline Impact on Redox Homeostasis of Normal Human Melanocytes HEMn-LP Exposed to UVA Radiation and Hydrogen Peroxide. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22041642"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Rok, J., Rzepka, Z., Beberok, A., Pawlik, J., and Wrze\u015bniok, D. (2020). Cellular and Molecular Aspects of Anti-Melanoma Effect of Minocycline\u2014A Study of Cytotoxicity and Apoptosis on Human Melanotic Melanoma Cells. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21186917"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Rok, J., Kowalska, J., Rzepka, Z., Stencel, D., Skorek, A., Banach, K., and Wrze\u015bniok, D. (2023). The Assessment of Anti-Melanoma Potential of Tigecycline-Cellular and Molecular Studies of Cell Proliferation, Apoptosis and Autophagy on Amelanotic and Melanotic Melanoma Cells. Cells, 12.","DOI":"10.3390\/cells12121564"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"104790","DOI":"10.1016\/j.tiv.2020.104790","article-title":"Cytotoxic and proapoptotic effect of doxycycline\u2014An in vitro study on the human skin melanoma cells","volume":"65","author":"Rok","year":"2020","journal-title":"Toxicol. Vitro"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1016\/j.anai.2020.02.007","article-title":"Hypersensitivity to tetracyclines: Skin testing, graded challenge, and desensitization regimens","volume":"124","author":"Maciag","year":"2020","journal-title":"Ann. Allergy Asthma Immunol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"300060520922416","DOI":"10.1177\/0300060520922416","article-title":"Toxic epidermal necrolysis syndrome induced by tigecycline: A case report","volume":"48","author":"Yang","year":"2020","journal-title":"J. Int. Med. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"258","DOI":"10.1016\/j.jaad.2005.10.004","article-title":"Tetracyclines: Nonantibiotic properties and their clinical implications","volume":"54","author":"Sapadin","year":"2006","journal-title":"J. Am. Acad. Dermatol."},{"key":"ref_31","first-page":"2049936120952605","article-title":"Cutaneous Hyperpigmentation Secondary to High-Dose Tigecycline: A Case Report","volume":"7","author":"Alsemari","year":"2020","journal-title":"Ther. Adv. Infect. Dis."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.cbi.2019.02.005","article-title":"Chlortetracycline and melanin biopolymer\u2014The risk of accumulation and implications for phototoxicity: An in vitro study on normal human melanocytes","volume":"303","author":"Rok","year":"2019","journal-title":"Chem.-Biol. Interact."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"ofw033","DOI":"10.1093\/ofid\/ofw033","article-title":"Tigecycline Induced Hyperpigmentation of the Skin","volume":"3","author":"Vandecasteele","year":"2016","journal-title":"Open Forum Infect. Dis."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1016\/0014-4835(80)90047-0","article-title":"Interaction of drugs with ocular melanin in vitro","volume":"30","author":"Atlasik","year":"1980","journal-title":"Exp. Eye Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1016\/S0378-5173(01)00988-7","article-title":"Binding of doxycycline to keratin, melanin and human epidermal tissue","volume":"235","author":"Banning","year":"2002","journal-title":"Int. J. Pharm."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1016\/j.jphotobiol.2015.04.009","article-title":"Effect of tetracycline and UV radiation on melanization and antioxidant status of melanocytes","volume":"148","author":"Rok","year":"2015","journal-title":"J. Photochem. Photobiol. B: Biol."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Rok, J., Rzepka, Z., Kowalska, J., Banach, K., Beberok, A., and Wrze\u015bniok, D. (2021). Molecular and Biochemical Basis of Minocycline-Induced Hyperpigmentation\u2014The Study on Normal Human Melanocytes Exposed to UVA and UVB Radiation. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22073755"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.tiv.2017.12.008","article-title":"Phototoxic effect of oxytetracycline on normal human melanocytes","volume":"48","author":"Rok","year":"2018","journal-title":"Toxicol. Vitro"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3171","DOI":"10.18632\/oncotarget.6419","article-title":"Antibiotic drug tigecycline inhibits melanoma progression and metastasis in a p21CIP1\/Waf1-dependent manner","volume":"7","author":"Hu","year":"2016","journal-title":"Oncotarget"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1111\/j.1749-6632.1994.tb24731.x","article-title":"Doxycycline and chemically modified tetracyclines inhibit gelatinase A (MMP-2) gene expression in human skin keratinocytes","volume":"732","author":"Uitto","year":"1994","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4446","DOI":"10.1158\/0008-5472.CAN-15-1626","article-title":"Tetracycline antibiotics impair mitochondrial function and its experimental use confounds research","volume":"75","author":"Chatzispyrou","year":"2015","journal-title":"Cancer Res."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Eaton, S.R., Eaton, G.R., and Berliner, L.J. (2005). Biophysical Studies of Melanin. Biomedical EPR, Part A: Free Radicals, Metals, Medicine, and Physiology, Springer. Biological Magnetic Resonance.","DOI":"10.1007\/b138018"},{"key":"ref_43","first-page":"1334","article-title":"Examination by EPR spectroscopy of free radicals in melanins isolated from A-375 cells exposed on valproic acid and cisplatin","volume":"69","author":"Chodurek","year":"2012","journal-title":"Acta Pol. Pharm."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"105844","DOI":"10.1016\/j.tiv.2024.105844","article-title":"Streptomycin generates oxidative stress in melanin-producing cells: In vitro study with EPR spectroscopy evidence","volume":"98","author":"Rzepka","year":"2024","journal-title":"Toxicol. Vitro"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1165","DOI":"10.1002\/jcb.26817","article-title":"Kanamycin induces free radicals formation in melanocytes: An important factor for aminoglycosides ototoxicity","volume":"120","author":"Rok","year":"2019","journal-title":"J. Cell. Biochem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1007\/s40828-021-00138-x","article-title":"Tetracycline Antibiotics","volume":"7","author":"Ramachanderan","year":"2021","journal-title":"ChemTexts"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1039\/C0AN00707B","article-title":"Tetracycline Speciation during Molecular Imprinting in Xerogels Results in Class-Selective Binding","volume":"136","author":"Mojica","year":"2011","journal-title":"Analyst"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"849","DOI":"10.32604\/biocell.2021.015900","article-title":"Biomedical Overview of Melanin. 1. Updating Melanin Biology and Chemistry, Physico-Chemical Properties, Melanoma Tumors, and Photothermal Therapy","volume":"45","author":"Stockert","year":"2021","journal-title":"BIOCELL"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Panzella, L., Ebato, A., Napolitano, A., and Koike, K. (2018). The Late Stages of Melanogenesis: Exploring the Chemical Facets and the Application Opportunities. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19061753"},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Micillo, R., Panzella, L., Koike, K., Monfrecola, G., Napolitano, A., and D\u2019Ischia, M. (2016). \u201cFifty Shades\u201d of Black and Red or How Carboxyl Groups Fine Tune Eumelanin and Pheomelanin Properties. Int. J. Mol. Sci., 17.","DOI":"10.3390\/ijms17050746"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1111\/j.1751-1097.2005.tb01532.x","article-title":"Comparison of Structural and Chemical Properties of Black and Red Human Hair Melanosomes","volume":"81","author":"Liu","year":"2005","journal-title":"Photochem. Photobiol."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"3754","DOI":"10.1039\/b902507c","article-title":"The Supramolecular Structure of Melanin","volume":"5","author":"Watt","year":"2009","journal-title":"Soft Matter"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1111\/j.1755-148X.2010.00771.x","article-title":"Is DHICA the Key to Dopachrome Tautomerase and Melanocyte Functions?","volume":"24","author":"Panzella","year":"2011","journal-title":"Pigment. Cell Melanoma Res."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.1016\/j.freeradbiomed.2010.01.033","article-title":"Regulation of DHICA-Mediated Antioxidation by Dopachrome Tautomerase: Implica-tion for Skin Photoprotection against UVA Radiation","volume":"48","author":"Jiang","year":"2010","journal-title":"Free Radic. Biol. Med."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2465","DOI":"10.1080\/14786419.2018.1542391","article-title":"On the Antioxidant Activity of Eumelanin Biopigments: A Quantitative Comparison between Free Radical Scavenging and Redox Properties","volume":"34","author":"Cecchi","year":"2020","journal-title":"Nat. Prod. Res."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"98276","DOI":"10.1155\/2014\/498276","article-title":"Melanins: Skin Pigments and Much More\u2014Types, Structural Models, Biological Functions, and Formation Routes","volume":"2014","author":"Solano","year":"2014","journal-title":"New J. Sci."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1111\/pcmr.12410","article-title":"Chemical analysis of constitutive pigmentation of human epidermis reveals constant eumelanin to pheomelanin ratio","volume":"28","author":"Ito","year":"2015","journal-title":"Pigment. Cell Melanoma Res."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"474","DOI":"10.1111\/j.1755-148X.2009.00580.x","article-title":"Chemical analysis of late stages of pheomelanogenesis: Conversion of dihydrobenzothiazine to a benzothiazole structure","volume":"22","author":"Wakamatsu","year":"2009","journal-title":"Pigment. Cell Melanoma Res."},{"key":"ref_59","unstructured":"(2024, June 28). ACD\/Labs Releases ACD\/Labs Percepta. Available online: https:\/\/www.acdlabs.com\/resource\/acd-labs-releases-acd-labs-percepta\/."},{"key":"ref_60","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Gaussian, Inc.. Revision C.01."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3891","DOI":"10.1021\/acs.jcim.1c00203","article-title":"AutoDock Vina 1.2.0: New Docking Methods, Expanded Force Field, and Python Bindings","volume":"61","author":"Eberhardt","year":"2021","journal-title":"J. Chem. Inf. Model."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization and Multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J. Comput. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1007\/978-1-4939-2269-7_19","article-title":"Small-Molecule Library Screening by Docking with PyRx","volume":"1263","author":"Dallakyan","year":"2015","journal-title":"Methods Mol. Biol."},{"key":"ref_64","unstructured":"Syst\u00e8mes, D. (2016). BIOVIA Discovery Studio. Dassault Systmes BIOVIA, Discovery Studio Modeling Environment, Release 2017, Dassault Systmes."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/18\/8939\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:45:11Z","timestamp":1760035511000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/18\/8939"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9,13]]},"references-count":64,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2025,9]]}},"alternative-id":["ijms26188939"],"URL":"https:\/\/doi.org\/10.3390\/ijms26188939","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,9,13]]}}}