Laboratory of Organic Synthesis, HPLC , NMR
Responsible Prof. Samuele Rinaldi
Q165-091, Q165-084, Q165-256
Research activity
- Synthesis of bioactive compounds
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The group is involved in the synthesis of small polyfunctionalized molecules, mainly containing α-hydrazido acids and α- or β-amino acids, together with suitable hydrophobic moieties, with the aim of obtaining compounds with a specific biological activity. In particular, we are developing the synthesis of peptidomimetics based on α-hydrazido acids, which are analogues of natural amino acids, in order to find new bioactive structures that can lead to antibacterial drugs having as a target the phospholipid components of bacterial membrane, with also additional potential applications as carriers for lipophilic conventional drugs or as adjuvants that act synergistically with common antibiotics. The structures synthesized, in which natural amino acids are partly or completely replaced by synthetic residues with conformational restrictions favoring the formation of amphiphilic structures, are also resistant to proteolytic degradation. The group is also involved in the evaluation of the biological activity of the synthesized compounds, especially regarding the antimicrobial activity, the hemolytic and/or cytotoxic activity, and the resulting therapeutic index, exploiting the collaboration with other research groups with renowned experience in these fields. 
Ongoing research projects
- Synthesis of more active and less hemolytic amphiphilic α-hydrazido acids
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We are studying the bi- and tricharged cationic amphiphilic α-hydrazido acids containing the lipophilic R1 and R2 groups already used in the corresponding monocharged versions, with the aim of increasing their activity toward either Gram-(+) or Gram-(-) bacteria, as well as their selectivity toward eukaryotic cells. 
- Sinergy with common antibiotics
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The study of the effect of amphiphilic α-hydrazido acids together with common antibiotics, in order to increase their activity or restore it in the case of resistant strains, is already ongoing and it will continue with the evaluation of combinations of antibiotics with new differently functionalized α-hydrazido acids. 
- Synthesis of new compounds specific toward Gram-negative bacteria
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With the purpose of contrasting the insurgence of drug resistance in Gram-negative bacteria caused by LPS modifications, a few α-hydrazido acids that have already shown antimicrobial activity toward these strains will be conveniently functionalized, with the aim of obtaining more active and safer derivatives. 
Equipment
In addition to the equipment necessary for the organic synthesis, the following instruments are available
- HPLC HP 1100, with diversion valve and analytical/semipreparative reverse phase columns
- POLAX D polarimeter
- Beckmann OLIGO 1000 DNA/RNA synthesizer
- Additional facilities available at the SIMAU department
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- Benchtop NMR Bruker Fourier 80
- FT-IR spectrometer Perkin Elmer Spectrum GX
- LC-MS Shimadzu LCMS-2050, with single quadrupole mass spectrometer
- Perkin Elmer LS 50 spectrofluorometer
- BioTek Synergy HT microplate reader spectrophotometer
Staff
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Prof. Samuele Rinaldi tel. 071 2204233 |
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