A New Conformationally Restricted Mimetic of Dipeptide EG – Synthesis of an Analogue of FEG

Galeazzi, Roberta; Martelli, Gianluca; Marcucci, Eleonora; Mobbili, Giovanna; Natali, D.; Orena, Mario; Rinaldi, Samuele

doi:10.1002/ejoc.200700300

Cited by 11 publications

(8 citation statements)

References 38 publications

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“…The solvent effect was included by using the implicit water GB/SA solvation method [ 36 ], and duplicate conformations and those with an energy in excess of 6.0 kcal mol −1 above the global minimum were discarded. The cluster analysis was performed within the Macromodel package using X-cluster following a protocol already reported [ 37 , 38 , 39 , 40 , 41 , 42 ]. Then, for each compound (EGCG and CHEMS), we carried out the clustering considering the RMSD of the main carbons skeleton (threshold value RMSD = 0.5) as filter.…”

Section: Methodsmentioning

confidence: 99%

Liposomal Formulations for an Efficient Encapsulation of Epigallocatechin-3-Gallate: An In-Silico/Experimental Approach

et al. 2018

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As a part of research project aimed to optimize antioxidant delivery, here we studied the influence of both salts and lipid matrix composition on the interaction of epigallocatechin-3-gallate (EGCG) with bilayer leaflets. Thus, we combined in silico and experimental methods to study the ability of neutral and anionic vesicles to encapsulate EGCG in the presence of Ca2+ and Mg2+ divalent salts. Experimental and in silico results show a very high correlation, thus confirming the efficiency of the developed methodology. In particular, we found out that the presence of calcium ions hinders the insertion of EGCG in the liposome bilayer in both neutral and anionic systems. On the contrary, the presence of MgCl2 improves the insertion degree of EGCG molecules respect to the liposomes without divalent salts. The best and most efficient salt concentration is that corresponding to a 5:1 molar ratio between Mg2+ and EGCG, in both neutral and anionic vesicles. Concerning the lipid matrix composition, the anionic one results in better promotion of the catechin insertion within the bilayer since experimentally we achieved 100% EGCG encapsulation in the lipid carrier in the presence of a 5:1 molar ratio of magnesium. Thus, the combination of this anionic liposomal formulation with magnesium chloride, avoids time-consuming separation steps of unentrapped active principle and appears particularly suitable for EGCG delivery applications.

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Section: Methodsmentioning

confidence: 99%

Liposomal Formulations for an Efficient Encapsulation of Epigallocatechin-3-Gallate: An In-Silico/Experimental Approach

et al. 2018

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“…lowest energy minimum and the most populated conformers. 22,23 Furthermore, the lowest energy minimum, together with the representative structure of the most populated clusters, were optimized by DFT calculation using G09 suite of Gaussian 09, Revision D.01 soware, 24 at B3LYP/6-311G** level of theory, [25][26][27][28] in order to better take into account the electronic effects in the conformer's stabilization and populations. 18 For each search, at least 1000 starting structures for each variable torsion angle were generated and minimized until the gradient was less than 0.05 kJÅ À1 mol À1 .…”

Section: Computational Methods and Proceduresmentioning

confidence: 99%

“…The cluster analysis was performed within the Macromodel package using Xcluster 20,21 following a protocol previously reported. 22,23 Furthermore, the lowest energy minimum, together with the representative structure of the most populated clusters, were optimized by DFT calculation using G09 suite of Gaussian 09, Revision D.01 soware, 24 at B3LYP/6-311G** level of theory, [25][26][27][28] in order to better take into account the electronic effects in the conformer's stabilization and populations.…”

Section: X-ray Measurementsmentioning

confidence: 99%

Liposome-based gene delivery systems containing a steroid derivative: computational and small angle X-ray diffraction study

et al. 2015

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In this study, the structural properties and the phase behaviour of mixed composition neutral liposomes containing a functionalized steroid are reported. With the aim to design neutral liposomes able to coordinate cations and to complex DNA, we synthesized cholesteryl-2-(picolinamido)-phenylcarbamate (CHOLp) containing an N-aryl picolinamide group as chelating agent linked to the steroid structure via a carbamate moiety. The phase behaviour of mixtures of the functionalized cholesterol (CHOLp) and dioleoyl-phosphatidylcholine (DOPC) was investigated by means of X-ray diffraction. Simultaneously, atomistic molecular dynamics simulations of DOPC/CHOLp bilayers as a function of CHOLp molar fractions were carried out to investigate the specific effects of the polar steroid on the structural and dynamic properties of these zwitterionic bilayers. The molecular modelling studies have been performed both in absence and in presence of bivalent cations salts in order to assess the CHOLp ability to coordinate metal ions. The results show good stability of the resulting DOPC/CHOLp bilayers which is improved by the presence of salt. This is particularly evident at low amount of CHOLp where a high order of the lipid tails can be observed, suggesting stabilization of the corresponding DOPC liposomes.This feature can be ascribed to the polar nature and structural properties of the ligand. In fact, due to the presence of the aromatic moieties, CHOLp combines two different behaviours, namely a propensity to realize both intermolecular p-stacking interactions and cation-p bonding mainly evident in CaCl 2 . The last feature confirms for CHOLp a role as a cation-mediated complexation agent for DNA. The X-ray diffraction data on the capability of DOPC/CHOLp liposomes to complex DNA was also reported.

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“…8 work directed to cyclic homoserine and aspartic acid analogues with an a quaternary carbon. In fact an additional alkyl substituent was introduced via the stereoselective alkylation of the chiral imine 7, easily prepared from the enantiomerically pure 3,4-trans-disubstituted pyrrolidin-2-one 5, already synthesized in our laboratory (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center

Crucianelli

Martelli

Orena

et al. 2009

Tetrahedron: Asymmetry

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A New Conformationally Restricted Mimetic of Dipeptide EG – Synthesis of an Analogue of FEG

Cited by 11 publications

References 38 publications

Liposomal Formulations for an Efficient Encapsulation of Epigallocatechin-3-Gallate: An In-Silico/Experimental Approach

Liposomal Formulations for an Efficient Encapsulation of Epigallocatechin-3-Gallate: An In-Silico/Experimental Approach

Liposome-based gene delivery systems containing a steroid derivative: computational and small angle X-ray diffraction study

New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center

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