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Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
Published on: September 19, 2022
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Synthesis of Cyclic Peptides as Potential Anti-Malarials
Catherine Fagundez1, Diver Sellanes1, Gloria Serra1
1Cátedra de Química Farmacéutica, (DQO), Facultad de Química , Universidad de la República , Gral. Flores 2124 , CP 11800 , Montevideo , Uruguay.
ACS Combinatorial Science
|February 16, 2018
Summary
Researchers synthesized cyclopeptides using Fmoc/solid-phase peptide synthesis (SPPS) and lactamization. One cyclopeptide demonstrated potent activity against a drug-resistant malaria parasite strain.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Parasitology
Background:
- Cyclopeptides are cyclic peptides with diverse biological activities.
- Drug-resistant strains of Plasmodium falciparum pose a significant threat to malaria control.
- Developing novel antimalarial agents is crucial.
Purpose of the Study:
- To synthesize cyclopeptides using Fmoc/SPPS and evaluate their antimalarial activity.
- To compare solution-phase and solid-phase lactamization methods for cyclopeptide synthesis.
- To identify potent cyclopeptides against chloroquine-resistant malaria.
Main Methods:
- Peptide synthesis utilizing 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) on a 2-chlorotrityl chloride (2-CTC) resin.
- Lactamization of peptides in solution or on solid phase to form cyclopeptides.
- In vitro evaluation of cyclopeptide activity against the chloroquine-resistant K1 strain of Plasmodium falciparum.
Main Results:
- Both solution-phase and solid-phase lactamization yielded desired cyclopeptides in good to very good yields.
- High cyclization efficiency was achieved, particularly for on-resin macrocyclization.
- Cyclo-Cys(Trt)-Gly-Thr(tBu)-Gly-Cys(Trt)-Gly exhibited potent and selective in vitro activity against Plasmodium falciparum K1 (EC50 = 28 nM).
Conclusions:
- Fmoc/SPPS combined with lactamization is an effective strategy for cyclopeptide synthesis.
- On-resin macrocyclization offers high cyclization efficiency.
- The synthesized cyclopeptide demonstrates significant potential as a novel antimalarial agent against resistant strains.
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