Núria Bayó‐Puxán

Institute for Research in Biomedicine

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Fernando Alberício

Biomedical Research Networking Center in Bioengineering, Biomaterials and Nanomedicine

Judit Tulla‐Puche

Universitat de Barcelona

Ernest Giralt

Universitat de Barcelona

Carmen Cuevas

PharmaMar (Spain)

Meritxell Teixidò

Institute for Research in Biomedicine

Jean‐Christophe Leroux

ETH Zurich

Mónica Varese

Institute for Research in Biomedicine

Andrés Francesch

PharmaMar (Spain)

Estela Riego

Universitat de Barcelona

Fayna García‐Martín

Universidad de La Rioja

Cooperative Institutions

Universitat de Barcelona

Institute for Research in Biomedicine

Biomedical Research Networking Center in Bioengineering, Biomaterials and Nanomedicine

Barcelona Biomedical Research Park

Consejo Superior de Investigaciones Científicas

FC Barcelona

Barcelona Institute for Science and Technology

ETH Zurich

Instituto de Salud Carlos III

Centro de Investigación Biomédica en Red

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Delivery of Nucleic Acids through the Controlled Disassembly of Multifunctional Nanocomplexes

Advanced Functional Materials (2009)

Mahmoud Elsabahy Nada Wazen Núria Bayó‐Puxán Glen F. Deleavey Marc J. Servant

Abstract In this study, novel pH‐responsive polyion complex micelles (PICMs) were developed for the efficient delivery of nucleic acid drugs, such as antisense oligonucleotide (AON) and short interfering RNA (siRNA). The PICMs consisted of a poly(amidoamine) (PAMAM) dendrimer–nucleic acid core and a detachable poly(ethylene glycol)‐ block ‐poly( propyl methacrylate‐ co ‐methacrylic acid) (PEG‐ b ‐P( Pr MA‐ co ‐MAA)) shell. The micelles displayed a mean hydrodynamic diameter ranging from 50 to 70 nm, a narrow size distribution, and a nearly neutral surface charge. They could be lyophilized without any additives and stored in dried form. Upon redispersion in water, no change in complexation efficiency or colloidal properties was observed. Entry of the micelles into cancers cells was mediated by a monoclonal antibody fragment positioned at the extremity of the PEG segment via a disulfide linkage. Upon cellular uptake and protonation of the MAA units in the acidic endosomal environment, the micelles lost their corona, thereby exposing their positively charged endosomolytic PAMAM/nucleic acid core. When these pH‐responsive targeted PICMs were loaded with AON or siRNAs that targeted the oncoprotein Bcl‐2, they exhibited a greater transfection activity than nontargeted PICMs or commercial PAMAM dendrimers. Moreover, their nonspecific cytotoxicity was lower than that of PAMAM. The pH‐responsive PICMs reported here appear as promising carriers for the delivery of nucleic acids.

Poly(N-isopropylacrylamide)

10.1002/adfm.200901139

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Citations (60)

Facile solid-phase synthesis of biotinylated alkyl thiols

Tetrahedron (2006)

Elisabet Prats‐Alfonso Fayna García‐Martín Núria Bayó‐Puxán Luis J. Cruz Mateu Pla‐Roca

Solid-Phase Synthesis

10.1016/j.tet.2006.04.090

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Citations (20)

AOA-2 Derivatives as Outer Membrane Protein A Inhibitors for Treatment of Gram-Negative Bacilli Infections

Frontiers in Microbiology (2021)

Rafael Ayerbe-Algaba Núria Bayó‐Puxán Ester Verdú Raquel Parra-Millán Jesús Seco

Previously, we identified that a cyclic hexapeptide AOA-2 inhibited the interaction of Gram-negative bacilli (GNB) like Acinetobacter baumannii , Pseudomonas aeruginosa , and Escherichia coli to host cells thereby preventing the development of infection in vitro and in a murine sepsis peritoneal model. In this work, we aimed to evaluate in vitro a library of AOA-2 derivatives in order to improve the effect of AOA-2 against GNB infections. Ten AOA-2 derivatives were synthetized for the in vitro assays. Their toxicities to human lung epithelial cells (A549 cells) for 24 h were evaluated by determining the A549 cells viability using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The effect of these peptide derivatives and AOA-2 at 250, 125, 62.5, and 31.25 μg/mL on the attachment of A. baumannii ATCC 17978, P. aeruginosa PAO1 and E. coli ATCC 25922 strains to A549 cells was characterized by adherence and viability assays. None of the 10 derivatives showed toxicity to A549 cells. RW01 and RW06 have reduced more the adherence of ATCC 17978, PAO1 and ATCC 2599 strains to A549 cells when compared with the original compound AOA-2. Moreover, both peptides have increased slightly the viability of infected A549 cells by PAO1 and ATCC 25922 than those observed with AOA-2. Finally, RW01 and RW06 have potentiated the activity of colistin against ATCC 17978 strain in the same level with AOA-2. The optimization program of AOA-2 has generated two derivatives (RW01 and RW06) with best effect against interaction of GNB with host cells, specifically against P. aeruginosa and E. coli .

Acinetobacter baumannii

Colistin

Viability assay

10.3389/fmicb.2021.634323

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Citations (6)

A New Approach to 3‐Hydroxyquinoline‐2‐carboxylic Acid.

ChemInform (2005)

Estela Riego Núria Bayó‐Puxán Carmen Cuevas Fernando Alberício Mercedes Álvarez

Abstract For Abstract see ChemInform Abstract in Full Text.

8-Hydroxyquinoline

10.1002/chin.200523137

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Citations (1)

Solid-Phase Synthesis of Oxathiocoraline

Synfacts (2007)

Judit Tulla‐Puche Fernando Alberício Núria Bayó‐Puxán Juan J. Moreno Andrés Francesch

The first solid-phase total synthesis of oxathiocoraline 1, a member of the quinoxaline antibiotic family, was achieved. Thus, from Wang resin 2 and Fmoc-Gly-OH, polymer-supported 3 was synthesized in 8 steps (89% purity). The key disulfide formation (dimerization) was performed with I2 in DMF to give 4. Cleavage of the dimer from the resin with concomitant cleavage of the Boc group, subsequent bismacrolactamization followed by incorporation of the heterocyclic unit afforded oxathiocoraline 1. Crude 1 was obtained in 7% overall yield after purification by semipreparative HPLC.

Solid-Phase Synthesis

Cleavage (geology)

10.1055/s-2007-968695

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The interactions of amphiphilic antisense oligonucleotides with serum proteins and their effects on in vitro silencing activity

Biomaterials (2012)

Arnaud E. Felber Núria Bayó‐Puxán Glen F. Deleavey Bastien Castagner Masad J. Damha

Conjugate

Serum Albumin

10.1016/j.biomaterials.2012.05.019

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Citations (18)

Cysteine-S-trityl a Key Derivative to PrepareN-Methyl Cysteines

Journal of Combinatorial Chemistry (2007)

Eleonora Marcucci Núria Bayó‐Puxán Judit Tulla‐Puche Jan Spengler Fernando Alberício

S-Trt Cys are used as precursors for the synthesis of protected NMe-Cys. N-Methylation of Alloc-Cys(Trt)-OH and Boc-Cys(Trt)-OH gives the corresponding N-methylated derivatives in good yields and purities, which can be further derivatized in solution to obtain a myriad of S-protected derivatives. To further broaden the scope of this methodology, the N (alpha)-amino protecting group of the NMe- S-protected Cys can be replaced easily either on the solid phase (from the Alloc precursor) or in solution (from the Boc precursor). Thus, this convenient route allows us to obtain many different protected NMe-Cys, which were of limited accessibility until now.

Derivative (finance)

10.1021/cc7001588

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Citations (16)

Total Solid‐Phase Synthesis of the Azathiocoraline Class of Symmetric Bicyclic Peptides

Chemistry - A European Journal (2006)

Núria Bayó‐Puxán Ariadna Fernández Judit Tulla‐Puche Estela Riego Carmen Cuevas

Thiocoraline is a potent antitumor agent isolated from the marine organism Micromonospora sp. This symmetric bicyclic depsipeptide binds the minor groove of DNA. Here we report two solid-phase strategies for the syntheses of azathiocoraline and its analogues. The thioester linkage was replaced by an amide bond to improve the compound's pharmacokinetic properties. The first strategy is based on a convergent (4+4) approach, whilst the second is a stepwise synthesis, cyclizations in both approaches occurring on the solid support. These two strategies were designed to overcome problems caused by the presence of consecutive noncommercial N-methyl amino acids, to avoid epimerization during cyclization and/or fragment condensation, and to form the disulfide bridge under solid-phase conditions. The heterocyclic moiety was added in the last step of the synthesis to assist the preparation of libraries of new compounds with potential therapeutic applications.

Moiety

Depsipeptide

Epimer

Amide

Oxazole

Solid-Phase Synthesis

Convergent synthesis

10.1002/chem.200600815

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Citations (28)

Combating virulence of Gram-negative bacilli by OmpA inhibition

Scientific Reports (2017)

Xavier Vila‐Farrés Raquel Parra-Millán Viviana Sánchez-Encinales Mónica Varese Rafael Ayerbe-Algaba

Preventing the adhesion of pathogens to host cells provides an innovative approach to tackling multidrug-resistant bacteria. In this regard, the identification of outer membrane protein A (OmpA) as a key bacterial virulence factor has been a major breakthrough. The use of virtual screening helped us to identify a cyclic hexapeptide AOA-2 that inhibits the adhesion of Acinetobacter baumannii, Pseudomonas aeruginosa and Escherichia coli to host cells and the formation of biofilm, thereby preventing the development of infection in vitro and in a murine sepsis peritoneal model. Inhibition of OmpA offers a strategy as monotherapy to address the urgent need for treatments for infections caused by Gram-negative bacilli.

Acinetobacter baumannii

Virulence factor

Gram-Negative Bacteria

10.1038/s41598-017-14972-y

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Citations (70)

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

Chemistry - A European Journal (2008)

Judit Tulla‐Puche Eleonora Marcucci Manuel Fermin Núria Bayó‐Puxán Fernando Alberício

Conformationally restricted mobility: The application of an efficient solid-phase strategy based on protection by conformationally restricted mobility (see scheme) has allowed, for the first time, the synthesis and determination of the biological activity of the two triostin A conformers, which result from the isomerization cis/trans of the N-methyl group of Cys. The most polar conformer showed the greatest inhibitory effect on cell growth. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2008/z800372_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Conformational isomerism

10.1002/chem.200800372

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Citations (15)