title: Synthesis of 4,4'-Diaminotriphenylmethanes with Potential Selective Estrogen Receptor Modulator (SERM)-like Activity.
abstract: In this study, a series of new 4,4'-diaminotriphenylmethanes was efficiently synthesized from aromatic aldehydes and 2,5-dimethoxybenzenamine under microwave irradiation in the presence of Sc(OTf)3 as a catalyst. Antiproliferative activity was assessed by using the MCF-7 estrogen receptor (ER)-positive breast cancer cell line, and antagonist/agonist transcriptional activities were determined. Docking studies and competition studies of triphenylmethanes and radiolabeled estradiol determined that these compounds do not bind the ER, indicating that triphenylmethane-induced changes in proliferative and transcriptional activities differ from conventional mechanisms of action triggered by other selective ER modulators.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206, La Laguna, Tenerife (Spain).
authors.forename: Gema
authors.initials: G
authors.lastname: Guedes
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206, La Laguna, Tenerife (Spain).
authors.forename: Ángel
authors.initials: Á
authors.lastname: Amesty
authors.affiliation: Instituto Universitario de Investigaciones Biomédicas y Sanitarias (IUIBS), Departamento de Ciencias Clínicas, BIOPHARM, Universidad de Las Palmas de Gran Canaria, Las Palmas de Gran Canaria, 35001 (Spain).
authors.forename: Roberto
authors.initials: R
authors.lastname: Jiménez-Monzón
authors.affiliation: Departamento de Biología Animal, Universidad de La Laguna, 38206 Tenerife (Spain).
authors.forename: Jorge
authors.initials: J
authors.lastname: Marrero-Alonso
authors.affiliation: Departamento de Biología Animal, Universidad de La Laguna, 38206 Tenerife (Spain).
authors.forename: Mario
authors.initials: M
authors.lastname: Díaz
authors.affiliation: Instituto Universitario de Investigaciones Biomédicas y Sanitarias (IUIBS), Departamento de Ciencias Clínicas, BIOPHARM, Universidad de Las Palmas de Gran Canaria, Las Palmas de Gran Canaria, 35001 (Spain).
authors.forename: Leandro
authors.initials: L
authors.lastname: Fernández-Pérez
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206, La Laguna, Tenerife (Spain). aestebra@ull.es.
authors.forename: Ana
authors.initials: A
authors.lastname: Estévez-Braun
mesh_terms: D001665:Binding Sites; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D006801:Humans; D061986:MCF-7 Cells; D008697:Methane / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D062105:Molecular Docking Simulation; D011485:Protein Binding; D017434:Protein Structure, Tertiary; D011960:Receptors, Estrogen / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D015533:Transcriptional Activation / Q000187:drug effects
chemical_list: D011960:Receptors, Estrogen; D020845:Selective Estrogen Receptor Modulators; D008697:Methane
keywords: estrogen receptors; molecular docking; selective modulation; triarylmethanes