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Special Issue "Cyclic Peptides"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Bioorganic Chemistry".

Deadline for manuscript submissions: 31 July 2018

Special Issue Editor

Guest Editor
Prof. Irene Izzo

Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi,di Salerno, 84084 Fisciano (SA), Italy
Website | E-Mail
Interests: organic synthesis; asymmetric synthesis; marine natural products; peptido mimetics; peptides; cyclopeptoids

Special Issue Information

Dear Colleagues,

In recent decades, considerable efforts have been devoted to the isolation, characterization and synthesis of peptide macrocycles. Natural compounds and synthetic analogues have found applications that range from therapeutics to bionanomaterials. This is due to their functional and structural properties, good bioavailability and enzymatic stability, when compared to their linear counterparts. From a therapeutic point of view, though cyclopeptides show a wide range of biological activities (anti-cancer, cytotoxic, antimicrobial, anthelmintic, anti-HIV and anti-insecticidal), to date few mechanisms of action and molecular receptors are known. This explains the growing interest of academia and pharmaceutical companies for peptide-based macrocycles. Considering that isolation from natural sources is expensive and time consuming, synthetic organic chemistry plays a crucial role for the preparation of these macrocyclic targets. However, the presence of unusual amino acids, heterocyclic building blocks and ester linkages still represent a challenge for synthetic chemists (as much as the macrocyclization step itself). The present Special Issue is aimed at covering recent isolated cyclopeptides, new synthetic strategies, as well as novel applications in different areas of this intriguing class of compounds, being that the research on macrocycles is promising, exciting and still underexplored.

Prof. Irene  Izzo
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • natural products
  • peptides
  • depsipeptides
  • macrocyclization
  • therapeutic agents
  • bionanomaterials

Published Papers (3 papers)

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Research

Open AccessArticle Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides
Molecules 2018, 23(7), 1779; https://doi.org/10.3390/molecules23071779
Received: 6 July 2018 / Revised: 13 July 2018 / Accepted: 14 July 2018 / Published: 19 July 2018
PDF Full-text (2952 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Cyclic peptoids have recently emerged as an important class of bioactive scaffolds with unique conformational properties and excellent metabolic stabilities. In this paper, we describe the design and synthesis of novel cyclic octamer peptoids as simplified isosters of mycotoxin depsipeptides bassianolide, verticilide A1,
[...] Read more.
Cyclic peptoids have recently emerged as an important class of bioactive scaffolds with unique conformational properties and excellent metabolic stabilities. In this paper, we describe the design and synthesis of novel cyclic octamer peptoids as simplified isosters of mycotoxin depsipeptides bassianolide, verticilide A1, PF1022A and PF1022B. We also examine their complexing abilities in the presence of sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB) salt and explore their general insecticidal activity. Finally, we discuss the possible relationship between structural features of free and Na+-complexed cyclic octamer peptoids and bioactivities in light of conformational isomerism, a crucial factor affecting cyclic peptoids’ biomimetic potentials. Full article
(This article belongs to the Special Issue Cyclic Peptides)
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Graphical abstract

Open AccessArticle Identification of Peptides in Flowers of Sambucus nigra with Antimicrobial Activity against Aquaculture Pathogens
Molecules 2018, 23(5), 1033; https://doi.org/10.3390/molecules23051033
Received: 27 March 2018 / Revised: 25 April 2018 / Accepted: 26 April 2018 / Published: 27 April 2018
PDF Full-text (1550 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The elder (Sambucus spp.) tree has a number of uses in traditional medicine. Previous studies have demonstrated the antimicrobial properties of elderberry liquid extract against human pathogenic bacteria and also influenza viruses. These properties have been mainly attributed to phenolic compounds. However,
[...] Read more.
The elder (Sambucus spp.) tree has a number of uses in traditional medicine. Previous studies have demonstrated the antimicrobial properties of elderberry liquid extract against human pathogenic bacteria and also influenza viruses. These properties have been mainly attributed to phenolic compounds. However, other plant defense molecules, such as antimicrobial peptides (AMPs), may be present. Here, we studied peptide extracts from flowers of Sambucus nigra L. The mass spectrometry analyses determined peptides of 3 to 3.6 kDa, among them, cysteine-rich peptides were identified with antimicrobial activity against various Gram-negative bacteria, including recurrent pathogens of Chilean aquaculture. In addition, membrane blebbing on the bacterial surface after exposure to the cyclotide was visualized by SEM microscopy and SYTOX Green permeabilization assay showed the ability to disrupt the bacterial membrane. We postulate that these peptides exert their action by destroying the bacterial membrane. Full article
(This article belongs to the Special Issue Cyclic Peptides)
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Figure 1

Open AccessFeature PaperArticle Chemical Synthesis and Functional Analysis of VarvA Cyclotide
Molecules 2018, 23(4), 952; https://doi.org/10.3390/molecules23040952
Received: 29 March 2018 / Revised: 14 April 2018 / Accepted: 17 April 2018 / Published: 19 April 2018
PDF Full-text (2415 KB) | HTML Full-text | XML Full-text
Abstract
Cyclotides are circular peptides found in various plant families. A cyclized backbone, together with multiple disulfide bonds, confers the peptides’ exceptional stability against protease digestion and thermal denaturation. In addition, the features of these antimicrobial molecules make them suitable for use in animal
[...] Read more.
Cyclotides are circular peptides found in various plant families. A cyclized backbone, together with multiple disulfide bonds, confers the peptides’ exceptional stability against protease digestion and thermal denaturation. In addition, the features of these antimicrobial molecules make them suitable for use in animal farming, such as aquaculture. Fmoc solid phase peptide synthesis on 2-chlorotrityl chlorine (CTC) resin using the “tea-bag” approach was conducted to generate the VarvA cyclotide identified previously from Viola arvensis. MALDI-TOF mass spectrometry determined the correct peptide amino acid sequence and the cyclization sites-critical in this multicyclic compound. The cyclotide showed antimicrobial activity against various Gram-negative bacteria, including recurrent pathogens present in Chilean aquaculture. The highest antimicrobial activity was found to be against Flavobacterium psychrophilum. In addition, membrane blebbing on the bacterial surface after exposure to the cyclotide was visualized by SEM microscopy and the Sytox Green permeabilization assay showed the ability to disrupt the bacterial membrane. We postulate that this compound can be proposed for the control of fish farming infections. Full article
(This article belongs to the Special Issue Cyclic Peptides)
Figures

Figure 1

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