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oai:docta.ucm.es:20.500.14352/1228542025-07-30T00:08:53Zcom_20.500.14352_14col_20.500.14352_15

Design and sustainable synthesis of small mannose-based glycodendrons as ligands for HIV-1 envelope protein gp120: Toward an explanation for their binding Perona Requena, Almudena Ramírez López, Pedro Suárez Álvarez, José Ramón Hernáiz Gómez-Degano, María Josefa Martínez Espinosa, Carlos Antonio Merchán, Alejandro 615:54 615.31 612.396 577.114 578 612.017 Glycodendrons Glycodendrimers Click chemistry Immunodeficiency virus HIV-1 gp120 binders Carbohydrate-protein interactions Ciencias Ciencias Biomédicas Química Química orgánica (Química) Química farmaceútica Farmacia Biología 24 Ciencias de la Vida 23 Química 3303.05 Síntesis Química 2306.06 Química de Los Hidratos de Carbono 2420 Virología 2412 Inmunología The 1H NMR and 13C NMR spectra were carried out at CAI Unidad de Resonancia Magnética (UCM). The authors gratefully acknowledge financial support provided by the Spanish Ministerio de Ciencia e Innovacion, ´ Grants RTI2018-096037B-I00, TED2021-130430B-C21, and PDC2022-133817-I00. On the basis of the interesting properties that glucuronic acid-based glycodendrimers and glycodendrons show against Dengue virus through their interaction with its envelope protein, herein we describe the design, sustainable synthesis and anti HIV-1 evaluation of a series of mannose-based glycodendrimers bearing different scaffolds, valency and functional groups at the focal position. Their sustainable chemical synthesis was performed using microwave-assisted copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction to yield glycoconjugates with full conversions (99%), allowing the reduction of the reaction time from 16 h to 60–120 min. Surface plasmon resonance studies have demonstrated that the small mannose-based glycodendrons (divalent derivatives) give the best binding interactions with the HIV-1 gp120 envelope protein, being the most active those that have a methoxymethyl group or an azidomethyl group at the focal position. Molecular modeling studies were carried out to simulate and explain the binding observed by surface plasmon resonance. This work reports a sustainable synthesis of small mannose-based glycodendrons as novel and potent anti HIV lead compounds. Ministerio de Cienca e Innovación (España) Depto. de Química en Ciencias Farmacéuticas Fac. de Farmacia TRUE pub 2025-07-29T12:16:41Z 2025-07-29T12:16:41Z 2024 journal article VoR https://hdl.handle.net/20.500.14352/122854 XXXX-XXXX 10.1016/j.cattod.2023.114493 eng info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-096037B-I00 info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PDC2022-133817-I00/ES/BIOPRODUCION DE BIOSURFACTANTES CON APLICACION EN LA INDUSTRIA COSMETICA Y FARMACEUTICA: APROXIMACION SOSTENIBLE/ Carlos Martínez, Alejandro Merchán, Almudena Perona, Pedro Ramírez-López, José Ramón Suárez, María J. Hernáiz, Design and sustainable synthesis of small mannose-based glycodendrons as ligands for HIV-1 envelope protein gp120: Toward an explanation for their binding, Catalysis Today, Volume 429, 2024, 114493, restricted access application/pdf Elsevier