{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T11:06:52Z","timestamp":1775300812223,"version":"3.50.1"},"reference-count":48,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2023,11,23]],"date-time":"2023-11-23T00:00:00Z","timestamp":1700697600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia (FCT) and FEDER","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia (FCT) and FEDER","award":["PTDC\/QUI-OUT\/3143\/2021"],"award-info":[{"award-number":["PTDC\/QUI-OUT\/3143\/2021"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia (FCT) and FEDER","award":["SFRH\/BD\/05278\/2020"],"award-info":[{"award-number":["SFRH\/BD\/05278\/2020"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia (FCT) and FEDER","award":["REDE\/1517\/RMN\/2005"],"award-info":[{"award-number":["REDE\/1517\/RMN\/2005"]}]},{"name":"PhD grant","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"PhD grant","award":["PTDC\/QUI-OUT\/3143\/2021"],"award-info":[{"award-number":["PTDC\/QUI-OUT\/3143\/2021"]}]},{"name":"PhD grant","award":["SFRH\/BD\/05278\/2020"],"award-info":[{"award-number":["SFRH\/BD\/05278\/2020"]}]},{"name":"PhD grant","award":["REDE\/1517\/RMN\/2005"],"award-info":[{"award-number":["REDE\/1517\/RMN\/2005"]}]},{"name":"POCI 2010 (FEDER) and FCT","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"POCI 2010 (FEDER) and FCT","award":["PTDC\/QUI-OUT\/3143\/2021"],"award-info":[{"award-number":["PTDC\/QUI-OUT\/3143\/2021"]}]},{"name":"POCI 2010 (FEDER) and FCT","award":["SFRH\/BD\/05278\/2020"],"award-info":[{"award-number":["SFRH\/BD\/05278\/2020"]}]},{"name":"POCI 2010 (FEDER) and FCT","award":["REDE\/1517\/RMN\/2005"],"award-info":[{"award-number":["REDE\/1517\/RMN\/2005"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Bis(indolyl)methanes (BIMs) are a class of compounds that have been recognized as an important core in the design of drugs with important pharmacological properties, such as promising anticancer and antiparasitic activities. Here, we explored the biological activity of the BIM core functionalized with different (hetero)aromatic moieties. We synthesized substituted BIM derivatives with triphenylamine, N,N-dimethyl-1-naphthylamine and 8-hydroxylquinolyl groups, studied their photophysical properties and evaluated their in vitro antiproliferative and antiparasitic activities. The triphenylamine BIM derivative 2a displayed an IC50 of 3.21, 3.30 and 3.93 \u03bcM against Trypanosoma brucei, Leishmania major and HT-29 cancer cell line, respectively. The selectivity index demonstrated that compound 2a was up to eight-fold more active against the parasites and HT-29 than against the healthy cell line MRC-5. Fluorescence microscopy studies with MRC-5 cells and T. brucei parasites incubated with derivative 2a indicate that the compound seems to accumulate in the cell\u2019s mitochondria and in the parasite\u2019s nucleus. In conclusion, the BIM scaffold functionalized with the triphenylamine moiety proved to be the most promising antiparasitic and anticancer agent of this series.<\/jats:p>","DOI":"10.3390\/molecules28237728","type":"journal-article","created":{"date-parts":[[2023,11,23]],"date-time":"2023-11-23T03:45:56Z","timestamp":1700711156000},"page":"7728","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Polyaromatic Bis(indolyl)methane Derivatives with Antiproliferative and Antiparasitic Activity"],"prefix":"10.3390","volume":"28","author":[{"given":"Raquel C. R.","family":"Gon\u00e7alves","sequence":"first","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal"},{"name":"Advanced (Magnetic) Theranostic Nanostructures Lab, International Iberian Nanotechnology Laboratory, Av. Mestre Jos\u00e9 Veiga s\/n, 4715-330 Braga, Portugal"}]},{"given":"Pablo","family":"Pe\u00f1alver","sequence":"additional","affiliation":[{"name":"Instituto de Parasitolog\u00eda y Biomedicina L\u00f3pez Neyra, CSIC, PTS Granada, Avenida del Conocimiento 17, 18016 Armilla, Granada, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7915-4720","authenticated-orcid":false,"given":"Susana P. G.","family":"Costa","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2400-405X","authenticated-orcid":false,"given":"Juan C.","family":"Morales","sequence":"additional","affiliation":[{"name":"Instituto de Parasitolog\u00eda y Biomedicina L\u00f3pez Neyra, CSIC, PTS Granada, Avenida del Conocimiento 17, 18016 Armilla, Granada, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7996-1626","authenticated-orcid":false,"given":"Maria Manuela M.","family":"Raposo","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,11,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"95","DOI":"10.4103\/ijpvm.IJPVM_116_18","article-title":"Leishmania Vaccines Entered in Clinical Trials: A Review of Literature","volume":"10","author":"Moafi","year":"2019","journal-title":"Int. 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