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DRUG-PEPTIDE CONJUGATES: SOLID PHASE SYNTHESIS AND MASS SPECTROMETRIC CHARACTERIZATION
Abstract
Peptide-drug conjugates are therapeutic agents that combine one or more drug molecules with a peptide through a biodegradable linker. Even if the peptides used in synthesis of such conjugates have a smaller pharmacological action than the small molecule of organic drug, they easily penetrate the membranes and then bind to receptors. Peptide-drug conjugates are used in various fields, such as: (i) anticancer therapy; (ii) antimicrobial application; (iii) anti-inflammatory application. In the last decades, researchers have proposed the concept of prodrug, which has shown great potential in diverse conditions with starting point from peptides. Furthermore, solid phase organic chemistry continues to play a powerful role in the synthesis of combinatorial libraries either through a mix-and-split or a multiple parallel synthesis strategy. Here, we also report on the use of ultrasound, which allows a drastic reduction in reaction time and provides better selectivity. In addition, ultrasound may induce deacetylation of acetylsalicylic acid to salicylic acid or its derivative in the synthesis of a so called ASA-NAP conjugate, where ASA is acetylsalicylic acid and NAP, an anti-Alzheimer peptide (sequence: 1NAPVSIPQ8-NH2). After synthesis, the resulting drug peptides were purified by high performance liquid chromatography (HPLC) and characterized by MALDI-ToF mass spectrometry.
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