Design, synthesis and biological evaluation of antipicornaviral pyrrole-containing peptidomimetics

Design, synthesis and biological evaluation of antipicornaviral pyrrole-containing peptidomimetics

A series of new peptidomimetics based on the tripeptide sequence Z-Leu-Phe-Gln-OH were synthesized, with ten of these including the alpha-nitrogen atom of the N-terminal amino acid incorporated into the pyrrole cycle. The synthesized compounds were tested for antiviral activity by agar-diffusion pla...

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Bibliographic Details
Published in:Protein and peptide letters Vol. 14; no. 9; p. 917
Main Authors: Minchev, I, Vladimirova, S, Vezenkova, L, Bijeva, A, Moussis, V, Nikolaeva-Glomb, L, Tsikaris, V, Czeuz, M, Galabov, A
Format: Journal Article
Language:English
Published: Netherlands 01-09-2007
Subjects:
Agar
Antiviral Agents - chemical synthesis
Antiviral Agents - chemistry
Antiviral Agents - pharmacology
Biomimetic Materials - chemical synthesis
Biomimetic Materials - chemistry
Biomimetic Materials - pharmacology
Cell Line
Drug Design
Enterovirus B, Human - drug effects
Enterovirus B, Human - growth & development
Glutamine - chemistry
Humans
Leucine - chemistry
Peptides - chemistry
Phenylalanine - chemistry
Picornaviridae - drug effects
Picornaviridae - growth & development
Structure-Activity Relationship
Viral Plaque Assay
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Summary:A series of new peptidomimetics based on the tripeptide sequence Z-Leu-Phe-Gln-OH were synthesized, with ten of these including the alpha-nitrogen atom of the N-terminal amino acid incorporated into the pyrrole cycle. The synthesized compounds were tested for antiviral activity by agar-diffusion plaque inhibition test against Coxsackievirus B1 replication in FL cell. Four of the products were observed to possess an antiviral activity, which was proven to be significant for one product. N-terminal pyrrole moiety and C-terminal free carboxyl function are available in all active compounds. On the other hand, their corresponding -OBzl and -Obu t esters are inactive.
ISSN:0929-8665
DOI:10.2174/092986607782110220