dc.contributor.author | Charalambous, Anna | en |
dc.contributor.author | Koyioni, Maria | en |
dc.contributor.author | Antoniades, Ioanna | en |
dc.contributor.author | Pegeioti, Despoina | en |
dc.contributor.author | Eleftheriou, Iro | en |
dc.contributor.author | Michaelidou, Sophia S. | en |
dc.contributor.author | Amelichev, Stanislav A. | en |
dc.contributor.author | Konstantinova, L. S. | en |
dc.contributor.author | Rakitin, O. A. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.contributor.author | Skourides, Paris A. | en |
dc.creator | Charalambous, Anna | en |
dc.creator | Koyioni, Maria | en |
dc.creator | Antoniades, Ioanna | en |
dc.creator | Pegeioti, Despoina | en |
dc.creator | Eleftheriou, Iro | en |
dc.creator | Michaelidou, Sophia S. | en |
dc.creator | Amelichev, Stanislav A. | en |
dc.creator | Konstantinova, L. S. | en |
dc.creator | Rakitin, O. A. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.creator | Skourides, Paris A. | en |
dc.date.accessioned | 2019-11-04T12:50:18Z | |
dc.date.available | 2019-11-04T12:50:18Z | |
dc.date.issued | 2015 | |
dc.identifier.issn | 2040-2503 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/52970 | |
dc.description.abstract | A chemical genomic screen of an in-house library of small molecule heterocycles was carried out using Xenopus laevis embryos. This led to the identification of N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline (1c), which elicits loss of pigmentation in melanophores and the retinal pigment epithelium (RPE) of developing embryos, independent of the developmental stage of initial exposure. The phenotype was reversible, since pigmentation returned upon compound removal while analysis of neural crest cell markers (Pax7) and melanophore markers (Dct/Xtrp2) revealed that both neural crest precursors and fully differentiated melanophores were present in the dithiazole 1c treated embryos. A subsequent focused structure-activity relationship (SAR) study identified the more active dithiazole 4-benzyloxy-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-aniline (1l) and the need for a chlorine substituent at the dithiazole C-4 position. Both the initial chemical genomic screen and the focused SAR study highlighted the toxicity of (dithiazolylidene)aminoazines, and also of methoxyaniline (anisidine) analogues that hosted strong electron-withdrawing or electronegative substituents or acidic hydroxyl groups on the anisidine moiety. This study suggests that 1,2,3-dithiazoles can act as reversible melanin synthesis inhibitors, revealing a new biological activity for this class of compounds. The inhibition of melanin synthesis is medically relevant as a potential treatment for pigmentation disorders such as melasma. © The Royal Society of Chemistry 2015. | en |
dc.source | MedChemComm | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84929312191&doi=10.1039%2fc5md00052a&partnerID=40&md5=9a8cd47ac40bfc347979096ea2c761e8 | |
dc.subject | controlled study | en |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | nonhuman | en |
dc.subject | Article | en |
dc.subject | phenotype | en |
dc.subject | genomics | en |
dc.subject | animal cell | en |
dc.subject | animal tissue | en |
dc.subject | cell migration | en |
dc.subject | molecular weight | en |
dc.subject | drug synthesis | en |
dc.subject | concentration response | en |
dc.subject | embryo | en |
dc.subject | Xenopus laevis | en |
dc.subject | [(4 chloro 5h 1,2,3 dithiazol 5 ylidene)amino]arene derivative | en |
dc.subject | 1,2,3 dithiazole derivative | en |
dc.subject | 4 benzyloxy n (4 chloro 5h 1,2,3 dithiazol 5 ylidene)aniline | en |
dc.subject | 4 benzyloxy n (4 phenyl 5h 1,2,3 dithiazol 5 ylidene)aniline | en |
dc.subject | 4 benzyloxy n (4,5 dichloro 3h 1,2,3 dithiazol 5 ylidene)aniline | en |
dc.subject | 4 chloro 1,2,3 dithiazole derivative | en |
dc.subject | 4 methoxyanilino dithiazole | en |
dc.subject | 4 n butoxy n (4 chloro 5h 1,2,3 dithiazol 5 ylidene)aniline | en |
dc.subject | cell lineage | en |
dc.subject | diencephalon | en |
dc.subject | dithiazole 4 benzyloxy n (4 chloro 5h 1,2,3 dithiazol 5 ylidene)aniline | en |
dc.subject | immunofluorescence test | en |
dc.subject | melanin | en |
dc.subject | melanogenesis | en |
dc.subject | melanophore | en |
dc.subject | melanosome | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 2 methyl 4 trifluoromethoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 2,4 dimethoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 ethoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 fluoro 3 methoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 hydroxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 methoxy 2 methylaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 methoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 methylthioaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 4 n propoxyaniline | en |
dc.subject | n (4 chloro 5h 1,2,3 dithiazol 5 ylidene) 6 methoxypyridin 3 amine | en |
dc.subject | neural crest cell | en |
dc.subject | photoreceptor | en |
dc.subject | pigment epithelium | en |
dc.subject | pigmentation | en |
dc.subject | pyrrole derivative | en |
dc.subject | structure activity relation | en |
dc.subject | transcription factor PAX3 | en |
dc.subject | transcription factor PAX7 | en |
dc.title | 1,2,3-Dithiazoles-new reversible melanin synthesis inhibitors: A chemical genomics study | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1039/c5md00052a | |
dc.description.volume | 6 | |
dc.description.startingpage | 935 | |
dc.description.endingpage | 946 | |
dc.author.faculty | Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Βιολογικών Επιστημών / Department of Biological Sciences | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Cited By :2</p> | en |
dc.source.abbreviation | MedChemComm | en |
dc.contributor.orcid | Skourides, Paris A. [0000-0003-3502-5729] | |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.contributor.orcid | Koyioni, Maria [0000-0002-2786-7523] | |
dc.gnosis.orcid | 0000-0003-3502-5729 | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |
dc.gnosis.orcid | 0000-0002-2786-7523 | |