Natural and Synthetic Halogenated Amino Acids-Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics.
Anti-Bacterial Agents
/ chemistry
Antimicrobial Peptides
/ chemistry
Gram-Negative Bacteria
/ drug effects
Gram-Positive Bacteria
/ drug effects
Halogenation
Halogens
/ chemistry
Humans
Microbial Sensitivity Tests
Peptidomimetics
/ chemistry
Peptoids
/ chemistry
Proline
/ analogs & derivatives
Structure-Activity Relationship
antimicrobial peptides (AMPs)
bromo-tryptophan
fluoro amino acids
fluoro-proline
halogenation
peptides
structure-activity relationship
α- and β-peptoids
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
06 Dec 2021
06 Dec 2021
Historique:
received:
10
09
2021
revised:
16
11
2021
accepted:
26
11
2021
entrez:
10
12
2021
pubmed:
11
12
2021
medline:
15
2
2022
Statut:
epublish
Résumé
The 3D structure and surface characteristics of proteins and peptides are crucial for interactions with receptors or ligands and can be modified to some extent to modulate their biological roles and pharmacological activities. The introduction of halogen atoms on the side-chains of amino acids is a powerful tool for effecting this type of tuning, influencing both the physico-chemical and structural properties of the modified polypeptides, helping to first dissect and then rationally modify features that affect their mode of action. This review provides examples of the influence of different types of halogenation in amino acids that replace native residues in proteins and peptides. Examples of synthetic strategies for obtaining halogenated amino acids are also provided, focusing on some representative compounds and their biological effects. The role of halogenation in native and designed antimicrobial peptides (AMPs) and their mimetics is then discussed. These are in the spotlight for the development of new antimicrobial drugs to counter the rise of antibiotic-resistant pathogens. AMPs represent an interesting model to study the role that natural halogenation has on their mode of action and also to understand how artificially halogenated residues can be used to rationally modify and optimize AMPs for pharmaceutical purposes.
Identifiants
pubmed: 34885985
pii: molecules26237401
doi: 10.3390/molecules26237401
pmc: PMC8659048
pii:
doi:
Substances chimiques
Anti-Bacterial Agents
0
Antimicrobial Peptides
0
Halogens
0
Peptidomimetics
0
Peptoids
0
fluoro-proline
0
Proline
9DLQ4CIU6V
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
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