Calorimetry and Langmuir–Blodgett studies on the interaction of a lipophilic prodrug of LHRH with biomembrane models

• The amphiphilic properties of a LHRH prodrug with a lipoamino acid (LAA) were investigated.
• Its interaction with biomembrane models was studied, using phospholipid monolayers and liposomes.
• Differential Scanning Calorimetry (DSC) and Langmuir–Blodgett film techniques were applied.
• Conjugation with LAA improved the interaction of LHRH with the biomembrane models.
• The LAA moiety aided the transfer of the prodrug from an aqueous solution to the biomembrane model.

The interaction between an amphiphilic luteinizing hormone-releasing hormone (LHRH) prodrug that incorporated a lipoamino acid moiety (C12-LAA) with biological membrane models that consisted of multilamellar liposomes (MLVs) and phospholipid monolayers, was studied using Differential Scanning Calorimetry (DSC) and Langmuir–Blodgett film techniques. The effect of the prodrug C12[Q1]LHRH on the lipid layers was compared with the results obtained with the pure precursors, LHRH and C12-LAA.Conjugation of LHRH with a LAA promoiety showed to improve the peptide interaction with biomembrane models. Basing on the calorimetric findings, the LAA moiety aided the transfer of the prodrug from an aqueous solution to the biomembrane model.

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