Igor Marques

Igor Marques
University of Aveiro | UA · Department of Medical Sciences & iBiMED – Institute of Biomedicine

MSc in Pharmaceutical Biomedicine

About

41
Publications
4,602
Reads
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1,744
Citations
Additional affiliations
March 2012 - February 2017
University of Aveiro
Position
  • PhD Student
October 2011 - December 2011
University of Aveiro
Position
  • Tutor
September 2010 - present
University of Aveiro
Position
  • Molecular Modeling of Biological Membranes
Education
September 2009 - December 2011
University of Aveiro
Field of study
  • Pharmaceutical Medicine
September 2006 - June 2009
University of Aveiro
Field of study
  • Biomedical Sciences

Publications

Publications (41)
Article
Using the chemical versatility of the benzo[b]thiophene motif, an extensive library of 24 (thio)urea receptors, with different binding properties and lipophilicities, was prepared and included α,α‐, α,β‐, β,β‐, β,γ‐, α,γ‐, and γ,γ‐benzo[b]thiophene positional isomers, as well as β‐ or γ‐benzo[b]thiophene‐based molecules decorated with aliphatic cha...
Article
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the pre...
Article
Hydrogen sulfide (H 2 S) plays a crucial signalling role in a variety of physiological systems, existing as the hydrosulfide anion (HS ‐ ) at physiological pH. Combining the potency of halogen bonding (XB) for anion recognition in water with coumarin fluorophore incorporation in acyclic host structural design, the first XB receptors to bind and, mo...
Article
Full-text available
Hydrogen sulfide (H 2 S) plays a crucial signalling role in a variety of physiological systems, existing as the hydrosulfide anion (HS ‐ ) at physiological pH. Combining the potency of halogen bonding (XB) for anion recognition in water with coumarin fluorophore incorporation in acyclic host structural design, the first XB receptors to bind and, mo...
Preprint
Full-text available
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the pre...
Preprint
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the pre...
Preprint
Full-text available
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the pre...
Preprint
Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the pre...
Article
The powerful electron accepting ability of fullerenes makes them ubiquitous components in biomimetic donor-acceptor systems that model the intermolecular electron transfer processes of Nature’s photosynthetic centre. Exploiting perylene diimides (PDIs) as components in cyclic host systems for the non-covalent recognition of fullerenes is unpreceden...
Article
The anion binding and transport properties of an extensive library of thiophene‐based molecules are reported. Seventeen bis‐urea positional isomers, with different binding conformations and lipophilicities, were synthetized by the appendage of α‐, β‐thiophene or α‐, β‐, γ‐benzo[ b ]thiophene motifs to the ortho ‐phenylenediamine central core, yield...
Article
A novel strategy for the recognition of anions in water using charge-neutral σ-hole halogen bonding and chalcogen bonding acyclic hosts is demonstrated for the first time. Exploiting the intrinsic hydrophobicity of halogen and chalcogen bond donor atoms integrated into a foldamer structural molecular framework containing hydrophilic functionalities...
Article
Full-text available
A series of fluorinated tripodal tris-thioureas function as highly active anion transporters across lipid bilayers and cell membranes. Here, we investigate their mechanism of action using anion transport assays in cells and synthetic vesicles and molecular modelling of transporter–lipid interactions. When compared with non-fluorinated analogues, fl...
Article
Dicarboxylate isomer discrimination and fluorescence sensing properties of a chalcogen bonding receptor differs considerably from halogen and hydrogen bonding analogues.
Article
Full-text available
A comprehensive experimental and theoretical investigation of the transmembrane chloride transport promoted by four series of squaramide derivatives, with different degrees of fluorination, number of convergent N-H binding units and conformational shapes is reported. The experimental chloride binding and transport abilities of these small synthetic...
Article
The unprecedented application of a chiral halogen bonding [3]rotaxane host system for discrimination of stereo- and E/Z geometric dicarboxylate anion guest isomers is described. Synthesised by a chloride anion templation strategy, the [3]rotaxane host recognises dicarboxylates via formation of 1:1 stoichiometric sandwich complexes, which is support...
Article
The unprecedented application of a chiral halogen bonding [3]rotaxane host system for discrimination of stereo- and E/Z geometric dicarboxylate anion guest isomers is described. Synthesised by a chloride anion templation strategy, the [3]rotaxane host recognises dicarboxylates via formation of 1:1 stoichiometric sandwich complexes, which is support...
Article
The application of chiral interlocked host molecules for discrimination of guest enantiomers has been largely overlooked, which is surprising given their unique three-dimensional binding cavities capable of guest encapsulation. Herein, we combined the stringent linear geometric interaction constraints of halogen bonding (XB), the non-covalent inter...
Article
A novel dynamic [3]catenane consisting of a large four-station central macrocycle which incorporates a bay tetrachloro-functionalized perylene diimide (PDI) unit and two triazolium anion binding motifs, mechanically bonded with two smaller isophthalamide-containing macrocycles is constructed using an anion template synthetic methodology. Proton NMR...
Article
Electron-deficient heavy chalcogen atoms contain Lewis acidic σ-holes which are able to form attractive supramolecular interactions, known as chalcogen bonding (ChB), with Lewis bases. However, their potential in solution-phase anion binding applications is only just beginning to be realized in simple acyclic systems. Herein, we explore the 5-(meth...
Article
Perturbations in cellular chloride concentrations can affect cellular pH, autophagy and lead to the onset of apoptosis. With this in mind synthetic ion transporters have been used to disturb cellular ion homeostasis and thereby induce cell death; however, it is not clear whether synthetic ion transporters can also be used to disrupt autophagy. Here...
Article
A novel sapphyrin derivative was obtained from the reaction between a free-base sapphyrin and dimethyl acetylenedicarboxylate (DMAD). The formation of the new compound involved a double aza-Michael addition of two pyrrolic NH groups to a DMAD molecule, with the formation of a disubstituted ethano bridge. The NMR spectral data reveal a product with...
Article
Full-text available
The synthesis of the first halogen bonding [3]rotaxane host system containing a bis-iodo triazolium-bis-naphthalene diimide four station axle component is reported. Proton NMR anion binding titration experiments revealed the halogen bonding rotaxane is selective for nitrate over the more basic acetate, hydrogen carbonate and dihydrogen phosphate ox...
Article
Full-text available
The synthesis of the first halogen bonding [3]rotaxane host system containing a bis-iodo triazolium-bis-naphthalene diimide four station axle component is reported. Proton NMR anion binding titration experiments revealed the halogen bonding rotaxane is selective for nitrate over the more basic acetate, hydrogen carbonate and dihydrogen phosphate ox...
Article
Chiral halogen bonding (S)-BINOL-based receptors are demonstrated to enhance the enantioselective recognition and sensing of chiral anions compared to their hydrogen bonding analogues. Computational studies attribute this behaviour to the strict linearity of halogen bonding (XB) and steric environment conferred by the XB donor groups bridged by the...
Article
Full-text available
Anion transport by synthetic carriers (anionophores) holds promise for medical applications, especially the treatment of cystic fibrosis. Among the factors which determine carrier activity, the size and disposition of alkyl groups is proving remarkably important. Herein we describe a series of dithioureidodecalin anionophores, in which alkyl substi...
Article
The synthesis and anion-recognition properties of the first halogen-bonding rotaxane host to sense anions in water is described. The rotaxane features a halogen-bonding axle component, which is stoppered with water-solubilizing permethylated β-cyclodextrin motifs, and a luminescent tris(bipyridine)ruthenium(II)-based macrocycle component. (1) H NMR...
Article
Full-text available
Neutral bimetallic rhenium(I) bis-triazole pyrimidine halogen bonding (XB) and hydrogen bonding (HB) acyclic anion receptors are prepared and 1H NMR titration investigations reveal the XB receptor exhibits significantly superior anion recognition behaviour.
Article
Full-text available
A new dichloroazacalix[2]arene[2]triazine receptor () with two chiral urea binding moieties is reported. The binding affinity of this macrocycle was evaluated by (1)H NMR titrations in CDCl3 for the dicarboxylate anions oxalate (ox(2-)), malonate (mal(2-)), succinate (suc(2-)), glutarate (glu(2-)), diglycolate (dg(2-)), fumarate (fum(2-)), maleate...
Article
Halogen bonding (XB), the attractive interaction between an electron-deficient halogen atom and a Lewis base, has undergone a dramatic development as an intermolecular force analogous to hydrogen bonding (HB). However, its utilization in the solution phase remains underdeveloped. Furthermore, the design of receptors capable of strong and selective...
Article
A new rotaxane containing the 3-amido-phenyl-triazolium group incorporated into the interlocked structure's axle component has been prepared by a chloride anion templated clipping strategy. Proton NMR titration experiments reveal that the interlocked host displays a high degree of halide anion recognition in competitive 1 : 1 CDCl3-CD3OD solvent mi...
Article
The interaction of six tripodal synthetic chloride transmembrane transporters with a POPC bilayer was investigated by means of molecular dynamics simulations using the general Amber force field (GAFF) for the transporters and the LIPID11 force field for the phospholipids. These transporters are structurally simple molecules, based on the tris(2-ami...
Data
Full-text available
Small molecule synthetic anion transporters may have potential application as therapeutic agents for the treatment of diseases including cystic fibrosis and cancer. Understanding the factors that can dictate the anion transport activity of such transporters is a crucial step towards their application in biological systems. In this study a series of...
Article
The ability of a calix[4]arene derivative (CX-1), bearing four protonated -NH3(+) groups located in the upper rim and aliphatic tails in the lower rim, to interact with a 1,2-dioleoyl-sn-glycero-3-phosphorylcholine (DOPC) model bilayer and promote transmembrane chloride transport was investigated by molecular dynamics (MD) simulations. Unconstraine...
Article
Full-text available
Small molecule synthetic anion transporters may have potential application as therapeutic agents for the treatment of diseases including cystic fibrosis and cancer. Understanding the factors that can dictate the anion transport activity of such transporters is a crucial step towards their application in biological systems. In this study a series of...
Article
Full-text available
The transport of anions across biological membranes by small molecules is a growing research field due to the potential therapeutic benefits of these compounds. However, little is known about the exact mechanism by which these drug-like molecules work and which molecular features make a good transporter. An extended series of 1-hexyl-3-phenylthiour...
Article
Full-text available
Highly potent but structurally simple transmembrane anion transporters are reported that function at receptor to lipid ratios as low as 1 : 1 000 000. The compounds, based on the simple ortho-phenylenediamine-based bisurea scaffold, have been studied for their ability to facilitate chloride/nitrate and chloride/bicarbonate antiport, and HCl symport...
Article
A series of simple ortho-phenylenediamine-based bisureas have been synthesised and their ability to facilitate chloride/nitrate and chloride/bicarbonate antiport, and HCl symport processes assessed using a combination of ion selective electrode and fluorescence techniques. In addition, the transmembrane transport of dicarboxylate anions (maleate an...
Article
Full-text available
The transmembrane anion transport activity of a series of synthetic molecules inspired by the structure of tambjamine alkaloids can be tuned by varying the lipophilicity of the receptor, with carriers within a certain log P range performing best.
Article
A series of bis-indolylureas have been found to mediate chloride transport across vesicle bilayers. The anion transport activity of these receptors may be readily modulated by small structural changes to the receptor scaffold as shown by the combination of experimental chloride efflux studies and molecular dynamics simulations in water and POPC bil...

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Projects

Projects (2)
Project
Development of steroid-based chemical chaperones for protein aggregation.
Project
Transport of anions through lipid bilayers mediated by synthetic anion receptors.