Synthesis of a poly(ester) dendritic β-cyclodextrin derivative by “click” chemistry: Combining the best of two worlds for complexation enhancement

López-Méndez, Luis José; González-Méndez, Israel; Aguayo‐Ortiz, Rodrigo; Domı́nguez, Laura; Alcaráz-Estrada, Sofía Lizeth; Rojas-Aguirre, Yareli; Guadarrama, Patricia

doi:10.1016/j.carbpol.2017.12.049

Cited by 16 publications

(5 citation statements)

References 30 publications

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“…Aplicando la misma estrategia, llevamos al límite las capacidades de la química clic al aplicarla para obtener derivados dendronizados de βCD altamente impedidos estéricamente, ya que incorporamos dendrones de poliéster de diferentes pesos moleculares en las siete posiciones de la βCD [31,32]. El rendimiento fue sorprendentemente bueno (más del 80%) (Figura 7).…”

Section: Plataformas Moleculares Como Acarreadores De Moléculas Bioac...unclassified

Versátil como ninguna, la química clic y su trascendencia en áreas diversas: de la ciencia de materiales a la investigación farmacéutica

et al. 2023

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En el año 2022 se otorgó el premio Nobel de química a Carolyn R. Bertozzi, Morten Meldal y K. Barry Sharpless por sus aportaciones en el desarrollo de la química clic y la química bioortogonal. La trascendencia de este tipo de reacciones radica en que, por su sencillez, selectividad, eficiencia y tolerancia a diferentes medios, incluido el acuoso, ha impactado no sólo en la química sintética de moléculas complejas y materiales, sino también en el área farmacéutica, ya que, aplicando este tipo de reacciones es posible formar conjugados con biomoléculas como proteínas, abriendo la puerta a la exploración y comprensión de diversos procesos biológicos en los organismos vivos para acceder así a terapias dirigidas más eficientes. En el Instituto de Investigaciones en Materiales de la UNAM hemos aplicado esta reacción de manera exitosa para modificar directamente algunas moléculas bioactivas como la curcumina (antioxidante natural), mejorando sus propiedades fisicoquímicas como solubilidad y estabilidad química. Asimismo, aplicando reacciones clic se sintetizaron derivados de β-ciclodextrina como nuevos acarreadores de fármacos, incorporando sustituyentes altamente ramificados llamados dendrones que confieren un adecuado balance hidrofílico/hidrofóbico. Estas modificaciones nos permitieron optimizar su paso a través de las membranas celulares por difusión, y su capacidad para encapsular fármacos hidrofóbicos.

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Section: Plataformas Moleculares Como Acarreadores De Moléculas Bioac...unclassified

Versátil como ninguna, la química clic y su trascendencia en áreas diversas: de la ciencia de materiales a la investigación farmacéutica

et al. 2023

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“…The click reaction has been widely used to prepare β-cyclodextrin-based welldefined star polymer. Alkynyl terminally functionalized linear polymers such as PCL, PNIPAM, dendron-like PAMAM or alkyne-terminated βCD precursors could be efficiently grafted-onto the heptakis (6-deoxy-6-azido)-β-cyclodextrin via click chemistry [35,40,[44][45][46] . Herein, a grafting-onto strategy was applied to synthesize β- reported by Ai et al, who tried to graft α-alkyne-dextran onto (N3)7-βCD, and found that the steric hindrance of dextran could directly limit the coupling efficiency.…”

Section: Cell Apoptosismentioning

confidence: 99%

“…Hassan and coworkers reported the synthesis of biodendrimeric β-cyclodextrin as drug nanocarriers by attaching βCD residues to the primary or secondary face of the core βCD via a click reaction [33,34]. Seven poly(ester) dendrons were selectively attached to the primary face of βCD via click chemistry, and the product as a drug carrier greatly improved the water solubility of albendazole [35]. Shen and co-workers prepared cyclodextrincentred drug-conjugated amphiphilic star copolymers via the combination of controlled ring-opening polymerization and click chemistry.…”

Section: Introductionmentioning

confidence: 99%

Folic Acid Decorated <em>β</em>-Cyclodextrin-Based Poly(ε-Caprolactone)/Dextran Star Polymer with Disulﬁde Bond-Linker as Theranostic Nanoparticle for Tumor-Targeted MRI and Chemotherapy

Yang¹,

Wang²,

Yang³

et al. 2021

Preprint

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β-cyclodextrin-based star polymers have attracted much interest because of their unique structures and potential biomedical and biological applications. Herein, we synthesized well-defined folic acid (FA)-conjugated and disulfide bond-linked star polymer ((FA-Dex-SS)-βCD-(PCL)14) acted as theranostic nanoparticles for tumor-targeted magnetic resonance imaging (MRI) and chemotherapy. Theranostic nanoparticles were obtained by loading doxorubicin (DOX) and superparamagnetic iron oxide particles (SPIO) were loaded into the star polymer nanoparticles to obtain ((FA-Dex-SS)-βCD-(PCL)14@DOX/SPIO) theranostic nanoparticles. In vitro drug release studies showed that approximately 100% of the DOX was released from disulfide bond-linked theranostic nanoparticles within 24 h under a reducing environment in the presence of 10.0 mM GSH. DOX and SPIO could be delivered into HepG2 cells efficiently, owing to folate receptor-mediated endocytosis process of the nanoparticles and GSH triggered disulfide-bonds cleaving.Moreover, (FA-Dex-SS)-βCD-(PCL)14@DOX/SPIO showed strong MRI contrast enhancement properties. In conclusion, folate-decorated reduction-sensitive star polymeric nanoparticles are a potential theranostic nanoparticle candidate for tumor-targeted MRI and chemotherapy.

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“…SiHa, HeLa, and CaSki cells were cultured in DMEM advanced (Gibco™), supplemented with 8% fetal bovine serum (FBS Gibco™), 2x glutamine (Gibco™), and 1x penicillin and streptomycin (supplied by Gibco™), and cultured at 37 °C and 5% CO 2 . For viability in vitro studies, cells were trypsinized (Gibco™) and distributed in 96-well plates in a density of 50,000 cells per well in DMEM-advanced medium supplemented with 8% of FBS and 2x glutamine as previously described [53].…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of Pyrrolo[3,4-b]pyridin-5-ones via Multicomponent Reactions and In Vitro–In Silico Studies Against SiHa, HeLa, and CaSki Human Cervical Carcinoma Cell Lines

et al. 2019

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A series of 12 polysubstituted pyrrolo[3,4-b]pyridin-5-ones were synthesized via a one-pot cascade process (Ugi–3CR/aza Diels-Alder/N-acylation/decarboxylation/dehydration) and studied in vitro using human epithelial cervical carcinoma SiHa, HeLa, and CaSki cell line cultures. Three compounds of the series exhibited significative cytotoxicity against the three cell lines, with HeLa being the most sensitive one. Then, based on these results, in silico studies by docking techniques were performed using Paclitaxel as a reference and αβ-tubulin as the selected biological target. Worth highlighting is that strong hydrophobic interactions were observed between the three active molecules and the reference drug Paclitaxel, to the αβ-tubulin. In consequence, it was determined that hydrophobic–aromatic moieties of bioactive compounds and Paclitaxel play a key role in making stronger interactions to the ligand–target complex. A quantitative structure activity relationship (QSAR) study revealed that the six membered rings are the most significant molecular frameworks, being present in all proposed models for the in vitro-studied cell lines. Finally, also from the docking interpretation, a ligand-based pharmacophore model is proposed in order to find further potential polyheterocyclic candidates to bind stronger to the αβ-tubulin.

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Synthesis of a poly(ester) dendritic β-cyclodextrin derivative by “click” chemistry: Combining the best of two worlds for complexation enhancement

Cited by 16 publications

References 30 publications

Versátil como ninguna, la química clic y su trascendencia en áreas diversas: de la ciencia de materiales a la investigación farmacéutica

Versátil como ninguna, la química clic y su trascendencia en áreas diversas: de la ciencia de materiales a la investigación farmacéutica

Folic Acid Decorated <em>β</em>-Cyclodextrin-Based Poly(ε-Caprolactone)/Dextran Star Polymer with Disulﬁde Bond-Linker as Theranostic Nanoparticle for Tumor-Targeted MRI and Chemotherapy

Synthesis of Pyrrolo[3,4-b]pyridin-5-ones via Multicomponent Reactions and In Vitro–In Silico Studies Against SiHa, HeLa, and CaSki Human Cervical Carcinoma Cell Lines

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