Isoniazid interaction with phosphatidylcholine-based membranes

Marques, Amanda Vicente; Trindade, Paulo Marengo; Marques, Sheylla; Brum, Tania Mara Martini de; Harté, Etienne; Rodrigues, Marieli Oliveira; D’Oca, Marcelo Gonçalves Montes; Silva, Pedro Eduardo Almeida da; Pohlmann, Adriana Raffin; Alves, Isabel D.; Lima, Vânia Rodrigues de

doi:10.1016/j.molstruc.2013.08.029

Cited by 8 publications

(9 citation statements)

References 40 publications

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“…These interactions are probably hydrogen bonds or van der Waals forces, giving rise to slight changes in the liposome size, which cannot be detected by PCS analysis. In more detail, the interaction of the phosphate region of the phosphatidylcholine's polar heads with the INH molecules could enhance the choline motional freedom [28], affecting the packing of the lipid bilayer. This effect is coherent with the observed decrease of the lipid bilayer thickness, which shifts from 5.0 nm for the unloaded samples to 4.8/4.6 nm for the INH-loaded vesicles.…”

Section: Discussionmentioning

confidence: 99%

Drugs/lamellae interface influences the inner structure of double-loaded liposomes for inhaled anti-TB therapy: An in-depth small-angle neutron scattering investigation

Truzzi

Meneghetti

Mori

et al. 2019

Journal of Colloid and Interface Science

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Section: Discussionmentioning

confidence: 99%

Drugs/lamellae interface influences the inner structure of double-loaded liposomes for inhaled anti-TB therapy: An in-depth small-angle neutron scattering investigation

Truzzi

Meneghetti

Mori

et al. 2019

Journal of Colloid and Interface Science

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“…NMR technique as a very powerful analytical method has been applied to study structural and dynamic properties of phospholipid liposomes and interactions between various compounds and lipid membranes . For example, numerous 1 H NMR investigations on reverse micellar systems aimed at determination of the nature of phospholipid–water interactions were reported .…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical NMR studies of interaction between phenylalanine derivative and egg yolk lecithin

Wałęsa

Ptak

Siodłak

et al. 2014

Magnetic Reson in Chemistry

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The interaction of phenylalanine diamide (Ac-Phe-NHMe) with egg yolk lecithin (EYL) in chloroform was studied by (1)H and (13)C NMR. Six complexes EYL-Ac-Phe-NHMe, stabilized by N-H···O or/and C-H···O hydrogen bonds, were optimized at M06-2X/6-31G(d,p) level. The assignment of EYL and Ac-Phe-NHMe NMR signals was supported using GIAO (gauge including atomic orbital) NMR calculations at VSXC and B3LYP level of theory combined with STO-3Gmag basis set. Results of our study indicate that the interaction of peptides with lecithin occurs mainly in the polar 'head' of the lecithin. Additionally, the most probable lecithin site of H-bond interaction with Ac-Phe-NHMe is the negatively charged oxygen in phosphate group that acts as proton acceptor.

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“…The previous study by Marques et al was able to determine a dissociation constant (Kd) of INH with dimyristoylphosphatidylcholine (DMPC) supported bilayers to be 0.031 μmol by plasmon waveguide resonance. 60,62 With the observation that INH most likely prefers DPPE to DPPC, the Kd of INH with DPPE would most likely be lower than that found by Marques et al More studies are needed to determine the exact values and whether the difference in tail length would affect the Kd.…”

Section: Resultsmentioning

confidence: 95%

Structure Dependence of Pyridine and Benzene Derivatives on Interactions with Model Membranes

et al. 2018

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Pyridine based small molecule drugs, vitamins, and cofactors are vital for many cellular processes, but little is known about their interactions with membrane interfaces. These specific membrane interactions of these small molecules or ions can assist in diffusion across membranes or reach a membrane bound target This study explores how minor differences in small molecules (isoniazid, benzhydrazide, isonicotinamide, nicotinamide, picolinamide, and benzamide) can affect their interactions with model membranes. Langmuir monolayer studies of dipalmitoylphosphatidylcholine (DPPC) or dipalmitoylphosphatidylethanolamine (DPPE), in the presence of the molecules listed, show that isoniazid and isonicotinamide affect the DPPE monolayer at lower concentrations than the DPPC monolayer, demonstrating a preference for one phospholipid over the other. The Langmuir monolayer studies also suggest that nitrogen content and stereochemistry of the small molecule can affect the phospholipid monolayers differently. To determine the molecular interactions of the simple N-containing aromatic pyridines with a membrane-like interface, 1H 1D NMR and 1H-1H 2D NMR techniques were utilized to obtain information aboutposition and orientation of the molecules of interest within aerosol-OT (AOT) reverse micelles. These studies show that all six of the molecules reside near the AOT sulfonate headgroups and ester linkages in similar positions, but nicotinamide and picolinamide tilt at the water-AOT interface to varying degrees. Combined, these studies demonstrate that small structural changes of small N-containing molecules can affect their specific interactions with membrane-like interfaces, and specificity toward different membrane components.

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Isoniazid interaction with phosphatidylcholine-based membranes

Cited by 8 publications

References 40 publications

Drugs/lamellae interface influences the inner structure of double-loaded liposomes for inhaled anti-TB therapy: An in-depth small-angle neutron scattering investigation

Drugs/lamellae interface influences the inner structure of double-loaded liposomes for inhaled anti-TB therapy: An in-depth small-angle neutron scattering investigation

Experimental and theoretical NMR studies of interaction between phenylalanine derivative and egg yolk lecithin

Structure Dependence of Pyridine and Benzene Derivatives on Interactions with Model Membranes

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