Interaction of nitrofurantoin with lipid langmuir monolayers as cellular membrane models distinguished with tensiometry and infrared spectroscopy

Autor(es)

Machado, Andre C. ^[1] ; Caseli, Luciano ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Dept Chem, UNIFESP, BR-09913030 Diadema, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: COLLOIDS AND SURFACES B-BIOINTERFACES; v. 188, APR 2020.
• Citações Web of Science: 0

Resumo

Knowing how a drug interacts with cell membranes is important to understand and predict its effects at the molecular level. Therefore, we aimed to study the interaction of nitrofurantoin (NFT), a compound with potential antibiotic and antitumor properties, with lipidic biological interfaces using Langmuir monolayers. We employed the phospholipids 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS), which were spread on the surface of water to form Langmuir films, to investigate the membrane-drug interactions. The interaction of the drug with the lipid monolayers was evaluated by using surface pressure-area isotherms, surface pressure-time kinetic curves, Brewster angle microscopy (BAM), and polarization-modulated infrared reflection-absorption spectroscopy (PM-IRRAS). Nitrofurantoin shifted the isotherms to lower DPPC molecular areas, indicating monolayer condensation, and to higher DPPS molecular areas, indicating monolayer expansion. Meanwhile, BAM images showed the appearance of interfacial aggregates for DPPS, but not for DPPC, in the presence of NFT. PM-IRRAS spectra showed that bands related to methylene stretches changed their relative intensities and maximum position related to their asymmetric and symmetric modes for both lipids. This suggested an alteration of the monolayer packing degree and the conformational order of the lipid alkyl chains, which were related to an increase in configurational order for DPPS, but disorder for DPPC. In conclusion, NFT caused distinctive changes in the thermodynamic, morphological, and structural properties of DPPC and DPPS monolayers, which may be associated with its bioactivity in cellular membranes and other lipidic interfaces of pharmaceutical interest. (AU)

• Processo FAPESP: 19/03239-0 - Interfaces nanoestruturadas para a investigação de substâncias bioativas em modelos de membrana celular e para a construção de dispositivos optoeletrônicos enzimáticos
• Beneficiário: Luciano Caseli
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 18/25943-9 - Estudo da interação de nitrofurantoína em modelos de membrana celular através de filmes de Langmuir
• Beneficiário: André Campos Machado
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica