UV Properties and Loading into Liposomes of Quinoline Derivatives

Sara Battista,Alessandra Del Giudice,Vincenzo Marsicano,Luciano Galantini,Antonio Arcadi,Luisa Giansanti,Massimiliano Aschi,Elena Allegritti

doi:10.3390/colloids5020028

Sara Battista, Alessandra Del Giudice + Show 6 more

Open Access

https://doi.org/10.3390/colloids5020028

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Abstract

The scientific relevance of quinolines is strictly linked to the fine-tuning of their features by functionalizing the heterocyclic core. Consequently, the compounds of this class are very versatile and can be used as possible drugs for a lot of medical applications. In this work, the inclusion of eight synthetic quinoline derivatives in liposomes formulated with different lipids was investigated in terms of the encapsulation efficiency and to highlight the effect on the liposome size distribution and thermotropic behavior. Excellent encapsulation was accomplished with all the quinoline/phospholipid combinations. Differences in the interactions at the molecular level, dependent on the quinoline molecular scaffolds and lipid structure, were observed, which could significantly bias the interaction with the drug and its release in pharmaceutical applications. Experiments in combination with computational studies demonstrated that the UV absorption of quinolines with expanded conjugation could be affected by the environment polarity. This was probably due to a solvent-dependent ability of these quinolines to stack into aggregates, which could also occur upon inclusion into the lipid bilayer.

Highlights

Quinolines are well-known compounds mostly investigated for their biological properties [1,2]
Other applications are in the sensoristic area, for example, the recognition and the identification of different bacterial species [17] and/or the diagnosis of human pathologies exploiting the properties of synthetic florescent quinoline derivatives in the absence [18] or in the presence [19,20,21] of metal ions abundant in biological systems
A systematic analysis of the electronic properties of the ground and the lowest excited states for all the species from 1 to 8 in the gas phase was carried out with the aim of evaluating possible electronic effects provided by different substituents

Summary

Introduction

Quinolines are well-known compounds mostly investigated for their biological properties [1,2]. They are alkaloids both present in nature and prepared synthetically [3]. The heterocyclic nitrogen-containing skeleton is fundamental for biological activity, but the properties can be selected and improved by changing the nature of the substituents around the building block [4,5]. Other applications are in the sensoristic area, for example, the recognition and the identification of different bacterial species [17] and/or the diagnosis of human pathologies exploiting the properties of synthetic florescent quinoline derivatives in the absence [18] or in the presence [19,20,21] of metal ions abundant in biological systems

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