{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T18:16:54Z","timestamp":1760552214273,"version":"3.41.2"},"reference-count":62,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2024,11,20]],"date-time":"2024-11-20T00:00:00Z","timestamp":1732060800000},"content-version":"vor","delay-in-days":19,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chem Biol Drug Des"],"published-print":{"date-parts":[[2024,11]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Overexposure to blue light due to the excessive use of electronic devices has been implicated in premature skin aging and eye damage, among other injuries to health. This study aimed to synthesize two azo derivatives of the 2\u2010(amino\u20102\u2032\u2010hydroxyphenyl) benzoxazole and explore their potential as UV and blue light filters, proposing a new spectral profile. The synthesis of the heterocyclic compounds involved condensation reactions and diazotation. The derivatives 2\u2010(benzoxazol\u20102\u2010yl)\u20105\u2010[(2\u2010hydroxynaphthyl)diazenyl]phenol and 2\u2010(benzoxazol\u20102\u2010yl)\u20104\u2010[(2\u2010hydroxynaphthyl)diazenyl]phenol were synthesized with a yield greater than 70%. Solubility was evaluated in seven different solvents. The maximum absorption wavelengths (<jats:italic>\u03bb<\/jats:italic><jats:sub>max<\/jats:sub>) were determined using UV\u2013Vis scanning spectrophotometry in the range of 200\u2013600\u2009nm. Photostability was assessed using a solar simulator and the Sun protection factor (SPF) was determined using in\u00a0vitro methodology. Cytotoxicity was evaluated using the MTT assay in V79 cells. These compounds were able to absorb UVA, UVB, and blue light, with <jats:italic>\u03bb<\/jats:italic><jats:sub>max<\/jats:sub> ranging from 300 to 500\u2009nm and demonstrated photostability after 3\u2009h of exposure to solar simulator with an SPF higher than 45. The compounds exhibited solubility in all lipophilic solvents tested. Regarding cytotoxicity, IC50 values were comparable to other filters. These findings indicate that both compounds hold promise as potential organic filters.<\/jats:p>","DOI":"10.1111\/cbdd.70020","type":"journal-article","created":{"date-parts":[[2024,11,21]],"date-time":"2024-11-21T04:09:43Z","timestamp":1732162183000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Innovative Photoprotection Strategy: Development of 2\u2010(Benzoxazol\u20102\u2010Yl)[(2\u2010Hydroxynaphthyl)Diazenyl] Phenol Derivatives for Comprehensive Absorption of <scp>UVB<\/scp>, <scp>UVA<\/scp>, and Blue Light"],"prefix":"10.1111","volume":"104","author":[{"given":"Karen","family":"Sousa","sequence":"first","affiliation":[{"name":"Laboratory of Genetic Toxicology Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"},{"name":"Center for Research in Product and Development (CEPPED) Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2360-1557","authenticated-orcid":false,"given":"Jaqueline Nascimento","family":"Picada","sequence":"additional","affiliation":[{"name":"Laboratory of Genetic Toxicology Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gabriela Rodrigues","family":"da Silva","sequence":"additional","affiliation":[{"name":"Center for Research in Product and Development (CEPPED) Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Larissa da Cunha","family":"Solka","sequence":"additional","affiliation":[{"name":"Center for Research in Product and Development (CEPPED) Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Iuri Marques","family":"de Oliveira","sequence":"additional","affiliation":[{"name":"Department of Biophysics, Biotechnology Center Federal University of Rio Grande Do Sul (UFRGS)  Porto Alegre RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jo\u00e3o Antonio P\u00eagas","family":"Henriques","sequence":"additional","affiliation":[{"name":"Department of Biophysics, Biotechnology Center Federal University of Rio Grande Do Sul (UFRGS)  Porto Alegre RS Brazil"},{"name":"Postgraduate Program in Biotechnology and Medical Sciences University of Vale Do Taquari (UNIVATES)  Lajeado RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leandra Franciscato","family":"Campo","sequence":"additional","affiliation":[{"name":"Laboratory of New Organic Materials and Forensic Chemistry Federal University of Rio Grande Do Sul (UFRGS)  Porto Alegre RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dione Silva","family":"Corr\u00eaa","sequence":"additional","affiliation":[{"name":"Center for Research in Product and Development (CEPPED) Lutheran University of Brazil (ULBRA)  Canoas RS Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,11,20]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2016.08.036"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s43630\u2010023\u201000453\u2010x"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.2478\/acph\u20102013\u20100018"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/lsm.22794"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/s43630\u2010021\u201000114\u2010x"},{"key":"e_1_2_7_7_1","first-page":"376","volume-title":"Excited States in Organic Chemistry","author":"Barltrop J. A.","year":"2008"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2860(98)00822-9"},{"volume-title":"Ag\u00eancia Nacional de Vigil\u00e2ncia Sanit\u00e1ria","year":"2019","author":"Brazilian Pharmacopoeia","key":"e_1_2_7_9_1"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuro.2016.03.003"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521\u20103927(20000801)21:12<832::AID\u2010MARC832>3.0.CO;2\u2010Y"},{"key":"e_1_2_7_12_1","first-page":"49","article-title":"Sunscreen Formulation and Testing","volume":"116","author":"Caswell M.","year":"2001","journal-title":"Cosmetics & Toiletries Magazine"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic4002829"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.3109\/13880209.2014.924020"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s43630\u2010021\u201000043\u20109"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1111\/jocd.13854"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tiv.2021.105300"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1590\/s2175\u201097902022e20547"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.11.064"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1111\/ics.12572"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1023\/a:1012572930721"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2022.122050"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jdermsci.2023.06.007"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2017.07.019"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.3390\/md20110687"},{"volume-title":"Evaluation of Stability Data\u2014Scientific Guideline","year":"2003","author":"ICH Q1E","key":"e_1_2_7_26_1"},{"key":"e_1_2_7_27_1","unstructured":"ISO 10993\u20105.2009.\u201cInternational Standard. Biological Evaluation of Medical Devices\u2014Part 5: Tests for Cytotoxicity.\u201d In\u00a0Vitro Methods 10993\u201310995."},{"volume-title":"Determination of Sunscreen UVA Photoprotection in Vitro","year":"2021","author":"ISO 24443","key":"e_1_2_7_28_1"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.3390\/ph15030263"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.2174\/1389557520999201123210025"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26216728"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1111\/jocd.15576"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jaad.2020.04.079"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemosphere.2023.138455"},{"key":"e_1_2_7_35_1","first-page":"121","article-title":"Determination of Sun Protection Factor by Spectrophotometry","volume":"61","author":"Mansur J. S.","year":"1986","journal-title":"Anais Brasileiros de Dermatologia"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.11.019"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1111\/php.12137"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.compbiolchem.2019.01.003"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijerph2007040006"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022\u20101759(83)90303\u20104"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep11325"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1679196"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.btecx.2020.100021"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.06.046"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jlumin.2006.11.007"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.3390\/life13071513"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/d0dt02016h"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1467\u20102494.1999.181658.x"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1751-1097.1979.tb07090.x"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.envint.2023.108082"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.02.050"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotobiol.2016.02.038"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25071537"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1159\/000526720"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotobiol.2023.112703"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbio.201900102"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1529\u20108019.2009.01289.x"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2015.04.017"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jaad.2016.09.038"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1007\/978\u20103\u2010319\u201056017\u20105_26"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2014.10.001"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.18240\/ijo.2018.12.20"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201700265"}],"container-title":["Chemical Biology &amp; Drug Design"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/cbdd.70020","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,11,26]],"date-time":"2024-11-26T06:08:30Z","timestamp":1732601310000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/cbdd.70020"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11]]},"references-count":62,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2024,11]]}},"alternative-id":["10.1111\/cbdd.70020"],"URL":"https:\/\/doi.org\/10.1111\/cbdd.70020","archive":["Portico"],"relation":{},"ISSN":["1747-0277","1747-0285"],"issn-type":[{"type":"print","value":"1747-0277"},{"type":"electronic","value":"1747-0285"}],"subject":[],"published":{"date-parts":[[2024,11]]},"assertion":[{"value":"2024-04-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-04","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-20","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70020"}}