Xarxa d’innovació docent sobre avaluació

Presentació de la xarxa d’innovació docent sobre avaluació a la Jornada de Bones Pràctiques 201

Synthetic Cyclolipopeptides Selective against Microbial, Plant and Animal Cell Targets by Incorporation of D-Amino Acids or Histidine

Cyclolipopeptides derived from the antimicrobial peptide c(Lys-Lys-Leu-Lys-Lys-Phe-Lys-Lys-Leu-Gln) (BPC194) were prepared on solid-phase and screened against four plant pathogens. The incorporation at Lys5 of fatty acids of 4 to 9 carbon atoms led to active cyclolipopeptides. The influence on the antimicrobial activity of the Lys residue that is derivatized was also evaluated. In general, acylation of Lys1, Lys2 or Lys5 rendered the sequences with the highest activity. Incorporation of a D-amino acid maintained the antimicrobial activity while significantly reduced the hemolysis. Replacement of Phe with a His also yielded cyclolipopeptides with low hemolytic activity. Derivatives exhibiting low phytotoxicity in tobacco leaves were also found. Interestingly, sequences with or without significant activity against phytopathogenic bacteria and fungi, but with differential hemolysis and phytotoxicity were identified. Therefore, this study represents an approach to the development of bioactive peptides with selective activity against microbial, plant and animal cell targets. These selective cyclolipopeptides are candidates useful not only to combat plant pathogens but also to be applied in other fieldsFunding provided by grant numbers: AGL2009-13255-C02-02/AGR (SV, MP, LF) and AGL2012-39880-C02-02 (SV, MP, LF). These grants were obtained from the Ministerio de Economía y Competitividad of Spai

Peptide-mediated vectorization of metal complexes: conjugation strategies and biomedical applications

The rich chemical and structural versatility of transition metal complexes provide numerous novel paths to be pursued in the design of molecules that exert particular chemical of physicochemical effects that could operate over specific biological targets. However, the poor cell permeability of metallodrugs represents an important barrier for their therapeutic use. The conjugation between metal complexes and a functional peptide vector can be regarded as a versatile and potential strategy to improve their bioavailability and accumulation inside cells, and the site selectivity of their effect. This perspective lies on reviewing the recent advances on the design of metallopeptide conjugates for biomedical applications. Additionally, we highlight the studies where this approach has been directed towards the incorporation of redox active metal centers in living organisms for modulating the cellular redox balance, as a tool with application in anticancer therapyWe acknowledge financial support by Consolider Ingenio CSD/CSD2010-00065 from MICINN of Spain. We also thank the Catalan DIUE of the Generalitat de Catalunya (2014 SGR 862). X.R. thanks financial support from INNPLANTA project INP-2011-0059-PCT-420000-ACT

Exercicis Solucionats d'Elucidació Estructural de Compostos Orgànics

Aquest llibre ha estat creat amb l'objectiu de proporcionar als estudiants de l'assignatura Elucidació estructural de compostos orgànics, una col·lecció de problemes solucionats, que els ajudi en l'autoaprenentatge d'aquesta disciplina. Els exercicis d'aquest llibre han estat elaborats a partir de les dades espectroscòpiques de ressonància magnètica nuclear (RMN) de protó (1H) i/o de carboni-13 (13C) de compostos orgànics, publicades en revistes especialitzades d'índex d'impacte eleva

Antimicrobial activity of linear lipopeptides derived from BP100 towards plant pathogens

A collection of 36 lipopeptides were designed from the cecropin A-melittin hybrid peptide BP100 (H-Lys-Lys-Leu-Phe-Lys-Lys-Ile-Leu-Lys-Tyr-Leu-NH2) previously described with activity against phytopathogenic bacteria. These lipopeptides were synthesized on solid-phase and screened for their antimicrobial activity, toxicity and proteolytic stability. They incorporated a butanoyl, a hexanoyl or a lauroyl group at the N-terminus or at the side chain of a lysine residue placed at each position of the sequence. Their antimicrobial activity and hemolysis depended on the fatty acid length and its position. In particular, lipopeptides containing a butanoyl or a hexanoyl chain exhibited the best biological activity profile. In addition, we observed that the incorporation of the acyl group did not induce the overexpression of defense-related genes in tomato. Best lipopeptides were BP370, BP378, BP381, BP387 and BP389, which were highly active against all the pathogens tested (minimum inhibitory concentration of 0.8 to 12.5 μM), low hemolytic, low phytotoxic and significantly stable to protease degradation. This family of lipopeptides might be promising functional peptides useful for plant protectionThe work was supported by the following: Ministerio de Economía y Competitividad (ES); AGL2012-39880-C02-02; LM, EB, EM, LF, MP; Ministerio de Economía y Competitividad (ES); AGL2015-69876-C2-2-R; AO, LM, EB, EM, LF, MP; University of Girona (ES); MPCUDG2016/038; AO, LF, M

Exercicis Solucionats d'Elucidació Estructural de Compostos Orgànics [versió html]

Aquest llibre ha estat creat amb l'objectiu de proporcionar als estudiants de l'assignatura Elucidació estructural de compostos orgànics, una col·lecció de problemes solucionats, que els ajudi en l'autoaprenentatge d'aquesta disciplina. Els exercicis d'aquest llibre han estat elaborats a partir de les dades espectroscòpiques de ressonància magnètica nuclear (RMN) de protó (1H) i/o de carboni-13 (13C) de compostos orgànics, publicades en revistes especialitzades d'índex d'impacte eleva

Exercicis Solucionats d'Elucidació Estructural de Compostos Orgànics

Aquest llibre ha estat creat amb l'objectiu de proporcionar als estudiants de l'assignatura Elucidació estructural de compostos orgànics, una col·lecció de problemes solucionats, que els ajudi en l'autoaprenentatge d'aquesta disciplina. Els exercicis d'aquest llibre han estat elaborats a partir de les dades espectroscòpiques de ressonància magnètica nuclear (RMN) de protó (1H) i/o de carboni-13 (13C) de compostos orgànics, publicades en revistes especialitzades d'índex d'impacte eleva

Design, synthesis and biological evaluation of cyclic peptidotriazoles derived from BPC194 as novel agents for plant protection

The search for novel antimicrobial agents to be used for plant protection has prompted us to design analogues incorporating non-natural amino acids. Herein, we designed and synthesized cyclic peptidotriazoles derived from the lead antimicrobial cyclic peptide c(Lys-Lys-Leu3-Lys-Lys5-Phe-Lys-Lys-Leu-Gln) (BPC194). In particular, Leu3 and Lys5 were replaced by a triazolyl alanine, a triazolyl norleucine or a triazolyl lysine. These peptides were screened for their antibacterial activity against Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora and Pseudomonas syringae pv. syringae, for their hemolysis and for their phytotoxicity. Results showed that the type of triazolyl amino acid and the substituent present at the triazole influenced the antibacterial and hemolytic activities. Moreover, the position of this residue was also crucial for the hemolysis. The lead compounds BPC548 and BPC550 exhibited high antibacterial activity (MIC of 3.1 to 25 μM), low hemolysis (19 and 26% at 375 μM, respectively) and low phytotoxicity. Therefore, these analogues could be used as new leads for the development of effective agents to control pathogenic bacteria responsible for plant diseases of economic importanceThis work was supported by the Spanish Ministerio de Economía y Competitividad (MINECO) [grant numbers AGL2009-13255-C02-02/AGR and AGL2012-39880-C02-02

Assessment & Evaluation in Higher Education Student perceptions of peer assessment: an interdisciplinary study Student perceptions of peer assessment: an interdisciplinary study

Peer assessment provides students with multiple benefits during their learning process. The aim of our study is to examine students' perception of peer assessment. Questionnaires were administered before and after the peerassessment process to 416 students studying 11 different subjects in four different fields taught at the University of Girona. Results suggest that students have a positive predisposition towards this methodology, both before and after its implementation. Students perceive it as a both motivating and recommended methodology that facilitates the acquisition of learning at different levels. As for its limitations, students highlight the responsibility that comes with it and a certain amount of distrust in fellow students' abilities to peer-assess

Rational Design of Cyclic Antimicrobial Peptides Based on BPC194 and BPC198

A strategy for the design of antimicrobial cyclic peptides derived from the lead compounds c(KKLKKFKKLQ) (BPC194) and c(KLKKKFKKLQ) (BPC198) is reported. First, the secondary β-structure of BPC194 and BPC198 was analyzed by carrying out molecular dynamics (MD) simulations. Then, based on the sequence pattern and the β-structure of BPC194 or BPC198, fifteen analogues were designed and synthesized on solid-phase. The best peptides (BPC490, BPC918, and BPC924) showed minimum inhibitory concentration (MIC) values <6.2 μM against Pseudomonas syringae pv. syringae and Xanthomonas axonopodis pv. vesicatoria, and an MIC value of 12.5 to 25 μM against Erwinia amylovora, being as active as BPC194 and BPC198. Interestingly, these three analogues followed the structural pattern defined from the MD simulations of the parent peptides. Thus, BPC490 maintained the parallel alignment of the hydrophilic pairs K1–K8, K2–K7, and K4–K5, whereas BPC918 and BPC924 included the two hydrophilic interactions K3–Q10 and K5–K8. In short, MD simulations have proved to be very useful for ascertaining the structural features of cyclic peptides that are crucial for their biological activity. Such approaches could be further employed for the development of new antibacterial cyclic peptidesThis work was supported by the Ministerio de Economía y Competitividad (MINECO) [grant numbers AGL2009-13255-C02-02/AGR, AGL2012-39880-C02-02 and AGL2015-69876-C2-2-R]