Interactions of a Fungistatic Antibiotic, Griseofulvin, with Phospholipid Monolayers Used as Models of Biological Membranes

Corvis, Yohann; Barzyk, Wanda; Brezesinski, Gerald; Mrabet, Nadir T.; Badis, Mounia; Hecht, Sabrina; Rogalska, Ewa

doi:10.1021/la060998x

Cited by 44 publications

(35 citation statements)

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“…Therefore, the changes observed in the spectra are consistent with the penetration of ibuprofen into the hydrophobic tails inferred from the surface pressure isotherms. Figure 6b presents the C = O stretching band at 1740 cm À1 for DPPC monolayer at 30 mN m À1 which is according to literature [42][43][44]. However, crystals of ibuprofen show an intense C = O stretching band at 1721 cm À1 [45].…”

Section: Resultssupporting

confidence: 63%

Langmuir films containing ibuprofen and phospholipids

Geraldo

Pavinatto

Nobre

et al. 2013

Chemical Physics Letters

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a b s t r a c tThis study shows the incorporation of ibuprofen, an anti-inflammatory drug, in Langmuir monolayers as cell membrane models. Significant effects were observed for dipalmitoyl phosphatidyl choline (DPPC) monolayers with relevant changes in the elasticity of the monolayer. Dipalmitoyl phosphatidyl glycerol (DPPG) monolayers were affected by small concentrations of ibuprofen, from 1 to 5 mol%. For both types of monolayer, ibuprofen could penetrate into the hydrophobic part of the monolayer, which was confirmed with polarization-modulated infrared reflection-absorption spectroscopy (PM-IRRAS). Brewster angle microscopy (BAM) images showed that ibuprofen prevents the formation of large domains of DPPC. The pharmacological action should occur primarily with penetration of ibuprofen via electrically neutral phospholipid headgroups of the membrane.

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Section: Resultssupporting

confidence: 63%

Langmuir films containing ibuprofen and phospholipids

Geraldo

Pavinatto

Nobre

et al. 2013

Chemical Physics Letters

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“…The monolayer is then compressed, and the SP-area isotherms of the pure lipid and the lipid with drug or drug delivery system are compared. Apart from changes in SP, changes in lipid morphology at the air-water interface can be studied by Brewster angle microscopy 20, 21…”

Section: Examples Of Model Cell Membranementioning

confidence: 99%

Biophysical Interactions with Model Lipid Membranes: Applications in Drug Discovery and Drug Delivery

2009

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The transport of drugs or drug delivery systems across the cell membrane is a complex biological process, often difficult to understand because of its dynamic nature. In this regard, model lipid membranes, which mimic many aspects of cell-membrane lipids, have been very useful in helping investigators to discern the roles of lipids in cellular interactions. One can use drug-lipid interactions to predict pharmacokinetic properties of drugs, such as their transport, biodistribution, accumulation, and hence efficacy. These interactions can also be used to study the mechanisms of transport, based on the structure and hydrophilicity/hydrophobicity of drug molecules. In recent years, model lipid membranes have also been explored to understand their mechanisms of interactions with peptides, polymers, and nanocarriers. These interaction studies can be used to design and develop efficient drug delivery systems. Changes in the lipid composition of cells and tissue in certain disease conditions may alter biophysical interactions, which could be explored to develop target-specific drugs and drug delivery systems. In this review, we discuss different model membranes, drug-lipid interactions and their significance, studies of model membrane interactions with nanocarriers, and how biophysical interaction studies with lipid model membranes could play an important role in drug discovery and drug delivery.

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“…Corvis et al 39) studied the interactions of griseofulvin with lipid membranes trying to elucidate the mechanisms of GF-membrane interactions using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-dilauroyl-sn-glycero-3-phosphocholine (DLPC), and 1,2-myristoyl-sn-glycero-3-phosphoethanolamine (DMPE) monolayers spread at the air/water interface. They proposed that nonpolar interactions are by and large responsible for GF retention in the monolayers.…”

Section: Resultsmentioning

confidence: 99%

Improving the High Variable Bioavailability of Griseofulvin by SEDDS

2007

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Self-emulsifying drug delivery systems (SEDDS) are mixtures of oils and surfactants, ideally isotropic, and sometimes containing cosolvents, which emulsify spontaneously to produce fine oil-in-water emulsions when introduced into aqueous phase under gentle agitation.1) Recently, SEDDS have been formulated using medium chain triglyceride oils and nonionic surfactants, the latter being less toxic. Upon peroral administration, these systems form fine emulsions (or microemulsions) in gastro-intestinal tract (GIT) with mild agitation provided by gastric mobility.2,3) Potential advantages of these systems include enhanced oral bioavailability enabling reduction in dose, more consistent temporal profiles of drug absorption, selective targeting of drug(s) toward specific absorption window in GIT, and protection of drug(s) from the hostile environment in gut. [4][5][6] The process of self-emulsification proceeds through formation of liquid crystals (LC) and gel phases, the properties of which significantly affect the formation of droplets and interface available for partitioning of drug.5-9) Many workers claim various rational applications of SEDDS for delivering and targeting lipophilic drugs (e.g., WIN 54954, 1) N-4472, 10) idebenone, 11) coenzyme Q10, 12) vitamin E, 13) halofantrine, 14) and cyclosporin A. 15) However, very few reports are available of SEDDS of water insoluble or poorly soluble hydrophobic compounds. Therefore the concept of using griseofulvin in SEDDS was considered for the present study, where the drug is present in solution form.Griseofulvin is an antifungal agent first isolated from a Penicillium spp. in 1939. It is effective after oral ingestion and reaches the skin and hair. It is deposited primarily in keratin precursor cells. Ingestion with a heavy meal and reduction in particle size enhances the absorption of griseofulvin.16) Griseofulvin systematic (IUPAC) name is (2S,6ЈR)-7-chloro-2Ј,4,6-trimethoxy-6Ј-methyl-3H,4ЈH-spiro[1-benzofuran-2,1Ј-cyclohex[2]ene]-3,4Ј-dione (Fig. 1), and its formula is C 17 H 17 ClO 6 with molecular weight 352.766 g/mol. The compound is insoluble in water (8.64 mg/l). It has a logP/hydrophobicity 2.15 (partition system octanol/water), and its pK a /isoelectric point is not available.17) Griseofulvin inhibits fungal mitosis by disrupting the mitotic spindle through interaction with polymerized microtubules. 18)Griseofulvin is administered orally. Its microcrystalline and ultramicrocrystalline forms are available as tablets. The microcrystalline form also comes in a pediatric suspension form. The typical dose of microcrystalline form is 500-1000 mg/d. Ultramicrocrystalline form is administered at doses of 330-990 mg/d. 19) Since the bioavailability of poorly water-soluble drugs can be influenced by interactions with food or by the physicochemical conditions in the gastrointestinal (GI) tract, 20) oral preparation of griseofulvin is commonly prescribed to be administered according to a fixed dosing schedule. The oral bioavailability of griseofulvin is highly varia...

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Interactions of a Fungistatic Antibiotic, Griseofulvin, with Phospholipid Monolayers Used as Models of Biological Membranes

Cited by 44 publications

References 44 publications

Langmuir films containing ibuprofen and phospholipids

Langmuir films containing ibuprofen and phospholipids

Biophysical Interactions with Model Lipid Membranes: Applications in Drug Discovery and Drug Delivery

Improving the High Variable Bioavailability of Griseofulvin by SEDDS

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