Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties
Abstract In the present study, a series of aryl-substituted thioqunoline conjugated to thiosemicarbazide were rationally designed and synthesized. The formation of target compounds was confirmed by spectral characterization techniques such as IR, 1H-NMR, 13C-NMR, ESI–MS, and elemental analysis. Amon...
| Main Authors: | , , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2023-02-01
|
| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-28852-1 |
| _version_ | 1827984338153635840 |
|---|---|
| author | Milad Noori Reyhaneh Sabourian Ali Tasharoie Maliheh Safavi Aida Iraji Minoo Khalili Ghomi Navid Dastyafteh Cambyz Irajie Elham Zarenezhad Seyyed Mehrdad Mostafavi Pour Fatemeh Rasekh Bagher Larijani Mohsen Amini Mannan Hajimahmoodi Mohammad Mahdavi |
| author_facet | Milad Noori Reyhaneh Sabourian Ali Tasharoie Maliheh Safavi Aida Iraji Minoo Khalili Ghomi Navid Dastyafteh Cambyz Irajie Elham Zarenezhad Seyyed Mehrdad Mostafavi Pour Fatemeh Rasekh Bagher Larijani Mohsen Amini Mannan Hajimahmoodi Mohammad Mahdavi |
| author_sort | Milad Noori |
| collection | DOAJ |
| description | Abstract In the present study, a series of aryl-substituted thioqunoline conjugated to thiosemicarbazide were rationally designed and synthesized. The formation of target compounds was confirmed by spectral characterization techniques such as IR, 1H-NMR, 13C-NMR, ESI–MS, and elemental analysis. Among the synthesized derivatives, compound 10g bearing para-chlorophenyl moiety was proved to be the most potent tyrosinase inhibitor with an IC50 value of 25.75 ± 0.19 µM. Compound 10g as the most potent derivative exhibited a noncompetitive inhibition pattern against tyrosinase in the kinetic study. Furthermore, the in silico cavity detection, as well as the molecular docking assessments, were performed to follow the behavior of 10g within the proposed binding site. Besides, the toxicity of 10g and its potency to reduce the melanin content on A375 cell lines were also measured. Consequently, aryl-substituted thioqunolines conjugated to thiosemicarbazide might be a promising candidate in the cosmetics, medicine, and food industry as tyrosinase inhibitors. |
| first_indexed | 2024-04-09T22:58:42Z |
| format | Article |
| id | doaj.art-ac74c27d1a4d4f7681ba37f1ac3f6038 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-09T22:58:42Z |
| publishDate | 2023-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-ac74c27d1a4d4f7681ba37f1ac3f60382023-03-22T11:09:34ZengNature PortfolioScientific Reports2045-23222023-02-0113111710.1038/s41598-023-28852-1Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis propertiesMilad Noori0Reyhaneh Sabourian1Ali Tasharoie2Maliheh Safavi3Aida Iraji4Minoo Khalili Ghomi5Navid Dastyafteh6Cambyz Irajie7Elham Zarenezhad8Seyyed Mehrdad Mostafavi Pour9Fatemeh Rasekh10Bagher Larijani11Mohsen Amini12Mannan Hajimahmoodi13Mohammad Mahdavi14Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDrug and Food Control Department, Faculty of Pharmacy, Tehran University of Medical SciencesDrug and Food Control Department, Faculty of Pharmacy, Tehran University of Medical SciencesDepartment of Biotechnology, Iranian Research Organization for Science and Technology (IROST)Stem Cells Technology Research Center, Shiraz University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesLiosa Pharmed Parseh CompanyDepartment of Biology, Payame Noor University(PNU)Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical SciencesDrug and Food Control Department, Faculty of Pharmacy, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesAbstract In the present study, a series of aryl-substituted thioqunoline conjugated to thiosemicarbazide were rationally designed and synthesized. The formation of target compounds was confirmed by spectral characterization techniques such as IR, 1H-NMR, 13C-NMR, ESI–MS, and elemental analysis. Among the synthesized derivatives, compound 10g bearing para-chlorophenyl moiety was proved to be the most potent tyrosinase inhibitor with an IC50 value of 25.75 ± 0.19 µM. Compound 10g as the most potent derivative exhibited a noncompetitive inhibition pattern against tyrosinase in the kinetic study. Furthermore, the in silico cavity detection, as well as the molecular docking assessments, were performed to follow the behavior of 10g within the proposed binding site. Besides, the toxicity of 10g and its potency to reduce the melanin content on A375 cell lines were also measured. Consequently, aryl-substituted thioqunolines conjugated to thiosemicarbazide might be a promising candidate in the cosmetics, medicine, and food industry as tyrosinase inhibitors.https://doi.org/10.1038/s41598-023-28852-1 |
| spellingShingle | Milad Noori Reyhaneh Sabourian Ali Tasharoie Maliheh Safavi Aida Iraji Minoo Khalili Ghomi Navid Dastyafteh Cambyz Irajie Elham Zarenezhad Seyyed Mehrdad Mostafavi Pour Fatemeh Rasekh Bagher Larijani Mohsen Amini Mannan Hajimahmoodi Mohammad Mahdavi Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties Scientific Reports |
| title | Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties |
| title_full | Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties |
| title_fullStr | Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties |
| title_full_unstemmed | Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties |
| title_short | Thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti-melanogenesis properties |
| title_sort | thioquinoline derivatives conjugated to thiosemicarbazide as potent tyrosinase inhibitors with anti melanogenesis properties |
| url | https://doi.org/10.1038/s41598-023-28852-1 |
| work_keys_str_mv | AT miladnoori thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT reyhanehsabourian thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT alitasharoie thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT malihehsafavi thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT aidairaji thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT minookhalilighomi thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT naviddastyafteh thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT cambyzirajie thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT elhamzarenezhad thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT seyyedmehrdadmostafavipour thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT fatemehrasekh thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT bagherlarijani thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT mohsenamini thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT mannanhajimahmoodi thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties AT mohammadmahdavi thioquinolinederivativesconjugatedtothiosemicarbazideaspotenttyrosinaseinhibitorswithantimelanogenesisproperties |