Surface chemistry and spectroscopy studies on 1,4-naphthoquinone in cell membrane models using Langmuir monolayers

Abstract

Investigating the role of drugs whose pharmaceutical activity is associated with cell membranes is fundamental to comprehending the biochemical processes that occur on membrane surfaces. In this work, we examined the action of 1,4-naphthoquinone in lipid Langmuir monolayers at the air-water interface, which served as a model for half of a membrane, and investigated the molecular interactions involved with tensiometry and vibrational spectroscopy. The surface pressure-area isotherms exhibited a noticeable shift to a lower area in relation to 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dihexadecanoyl-sn-glycero-3-phospho-l-serine (DPPS) lipid monolayers, which indicated a disruption of the monolayer structure and solubilisation of the lipids towards the aqueous subphase. To better correlate to the action of this drug in biological membrane events, cell cultures that represented tumorigenic and non-tumorigenic cells were spread onto the air-water interface, and 1,4-naphthoquinone was then incorporated. While only slight changes were observed in the non-tumorigenic cells upon drug incorporation, significant changes were observed in the tumorigenic cells, on which the organisation of the Langmuir monolayers was disrupted as evidenced by tensiometry and vibrational spectroscopy. This work then shows that this drug interacts preferentially for specific surfaces. In simplified models, it has a higher effect for the negative charged DPPS rather than the zwitterionic DPPC; and for complex cell cultures, 1,4-naphthoquinone presents a more significant effect for that representing tumorigenic cells.

Interactions of bioactive molecules & nanomaterials with Langmuir monolayers as cell membrane models

“…Disruption of phospholipids structure and fluidizing effects were also observed for other anticancer drugs, such as toremifene [204] on DPPG monolayers, naphthoquinone [205] on DPPS and DPPC films, and the squalenoyl derivative of cytarabine, a pyrimidine nucleoside analog, on DMPC monolayers [206]. However, an opposite effect on PC monolayers (condensation) was reported for a very hydrophobic, natural polyphenol -curcumin [207].…”

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

“…The effect of 1,4-NQ on cell membrane models was studied by vibrational spectroscopy. [20] The interactions of 1,4-NQ with DNA have been investigated by Raman and Surface Enhanced Raman spectroscopy [21] to determine possible binding sites. However, in none of these studies detailed information at the atomic level was obtained.…”

“…In spite of this, there are very limited spectroscopic investigations focusing on this species. The effect of 1,4‐NQ on cell membrane models was studied by vibrational spectroscopy [20] . The interactions of 1,4‐NQ with DNA have been investigated by Raman and Surface Enhanced Raman spectroscopy [21] to determine possible binding sites.…”

Physical-Chemical Studies of the Effect of Antibiotic Incorporation in the Structure and Molecular Organization of Clinical-Grade Lung Surfactant Monolayers and Membrane Models at the Air-Water Interface

“…The maximum of CS -1 reached for pure Curosurf monolayers was around 100 mNm -1 at a surface pressure of 35 LALCHEV, 2014). Thus, low additions of drug (0.1 and 1% w/w) seems to maintain the monolayer order/packing of molecules in contrary to the highest addition (10% w/w) that increases its compressibility, as a result of a high content of new molecules which prevents the lipids from attaining a highly-packed structure (HUSSEIN et al, 2013). Also, two minima were observed in CS -1 curves.…”

“…Clarithromycin at a 0.1%, 1%, and 10% fractions shifts the isotherm to a slightly lower area. The condensation effect in π-A monolayers is usually related in literature to the stabilization of the lateral repulsion between the acyl chains (HUSSEIN et al, 2013). The effect appears to be common especially when there are charged lipids with ions (EBARA et al, 1994).…”