Design and synthesi̇s of lisine based novel organogelators as a drug carrier

Novel diamide- peptide derivatives, combination of L-lisine amide derivatives with n-alkanoyl-L-amino acids (alanine leusine, phenylalanine) were synthesised on the basis of peptide linker as a biocompatible drug carrier materials. Nε-palmitoyl-L-lisine ethyl and hexyl esters and Nε-myristoyl-L-lisine ethyl esters as a basic components and n-alkanoyl-L-amino acids derivatives of alanine, leusine, phenylalanine as acid components were used to acquire two component salt, as a precursor of diamide-peptide derivative.We used different amino acids (alanine leusine, phenylalanine), to make diversification of its acidic component in order to obtained diversified diamide-peptide derivatives. And also to understand the effect of lipophilicity of alkanoyl moieties various alkanoyl groups were used in the combinations of Lys/Ala, Lys/Leu, Lys/Phe peptidic backbone. For this purpose, diamide-peptide functionalized, D1, D2, D3, D4, D5, D6, D7 gelators, having three hydrogen-bonding sites were synthesised, respectively, from following salt combinations: Nε-palmitoil-L-lizin ethil ester-N-lauroil-L-alanine (PL/LA); Nε-palmitoyl-L-lisine ethyl ester-N-lauroyl-L-leusine (PL/LL); Nε-palmitoyl-L-lisine ethyl ester-N-lauroyl-L-phenylalanine (PL/ LFA); Nε-myristoyl-L-lisine ethyl ester-N-lauroyl-L-phenylalanine (ML/LFA); Nε-palmitoyl-L-lisine ethyl ester-N-myristoyl-L-phenylalanine (PL/MFA); Nε-palmitoyl-L-lisine hexyl ester-N-lauroyl-L-alanine (PLH/LA); Nε-myristoyl-L-lisine ethyl ester-N-lauroyl-L-alanine (ML/LA). In this way, seven novel diamide-peptide organogelator structures explored gelation ability in different pharmaceutical fluids, such as liquid paraffin and ethyl laurate, ethyl myristate and ethyl palmitate, and 1,2-propanediol (oils used widely in pharmaceutical formulation and tested for regulate termal behaviour of materials. FTIR was employed to see the effect of hydrogen bonding in the formation of gel network.Thermodynamic parameters regarding gel-to-sol transition were collected with van't Hoff relationships. Key Words:. Organogel, LMWGs ( low molecular wait organogelators), L-Lysine, diamde-peptide, SEM, self assembly, soft materials.