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  • Interaction of naproxen amphiphilic derivatives with biomembrane models evaluated by differential scanning calorimetry and Langmuir-Blodgett studies.

Interaction of naproxen amphiphilic derivatives with biomembrane models evaluated by differential scanning calorimetry and Langmuir-Blodgett studies.

Journal of colloid and interface science (2011-05-24)
Dorotea Micieli, Maria Chiara Giuffrida, Rosario Pignatello, Francesco Castelli, Maria Grazia Sarpietro
ABSTRACT

Anti-inflammatory drugs represent a potential new strategy for the treatment of Alzheimer's disease (AD). The ability to cross the blood-brain barrier and to reach brain tissues is a critical point for these drugs and is strictly related to their lipophilicity. Naproxen (NAP) is a non-steroidal anti-inflammatory drug (NSAIDs) under active investigation for AD. To improve its lipophilic character, NAP was conjugated through a diethylamine spacer (EDA) to lipoamino acids (LAA), α-amino acids containing a long alkyl side chain, to obtain the NAP-EDA-LAA10 and NAP-EDA-LAA14 prodrugs. The interaction of NAP and prodrugs with dimyristoylphosphatidylcholine phospholipids, forming either multilamellar vesicles or monolayers (at the air/water interface) and used as biomembrane models, was studied by differential scanning calorimetry and Langmuir-Blodgett techniques. Experimental data showed that NAP conjugation with LAA residues was able to enhance the drug interaction with such biomembrane models.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diethylamine hydrobromide, 98%
Sigma-Aldrich
Diethylamine hydrochloride, ReagentPlus®, 99%
Sigma-Aldrich
Diethylamine, purified by redistillation, 99.5%
Sigma-Aldrich
Diethylamine, ≥99.5%
Sigma-Aldrich
Diethylamine, puriss. p.a., ≥99.5% (GC)