Synthesis of versatile chemical tools toward a structure/properties relationships study onto targeting colloids

As part of a drug delivery project, four aldehydes of the type Pam-Lys(Pam)-spacer-CO-CHO were synthesized to be included in targeting colloids. Though amphiphilic, they were obtained within reasonable yields (18–55%) and with high RP-HPLC purity (∼90%). Parallely, six complementary targeting peptides of the type H2N-NH-CH2-CO-spacer-YGRGDSP-NH2 were prepared to be anchored onto colloids. Isolated yields are related to the spacer length and nature. To easily and rapidly modulate the distance between the peptide and the vesicle, every partners were elaborated on solid phase and the expected constructions were obtained by hydrazone ligation. One possible application is presented here with multilamellar vesicles targeting HUVEC cells. Preliminary results prove that the fine-tuning of the spacer length permits to optimize the recognition toward the target cells.

Graphical abstractIn a drug delivery project, four amphiphilic aldehydes and six hydrazinopeptides were synthesized to obtain targeting vesicles. The tuning of the spacer length influences the recognition toward the target cells.Figure optionsDownload full-size imageDownload as PowerPoint slide