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      Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

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          Abstract

          Peptides have gained increased interest as therapeutics during recent years. More than 60 peptide drugs have reached the market for the benefit of patients and several hundreds of novel therapeutic peptides are in preclinical and clinical development. The key contributor to this success is the potent and specific, yet safe, mode of action of peptides. Among the wide range of biologically-active peptides, naturally-occurring marine-derived cyclopolypeptides exhibit a broad range of unusual and potent pharmacological activities. Because of their size and complexity, proline-rich cyclic peptides (PRCPs) occupy a crucial chemical space in drug discovery that may provide useful scaffolds for modulating more challenging biological targets, such as protein-protein interactions and allosteric binding sites. Diverse pharmacological activities of natural cyclic peptides from marine sponges, tunicates and cyanobacteria have encouraged efforts to develop cyclic peptides with well-known synthetic methods, including solid-phase and solution-phase techniques of peptide synthesis. The present review highlights the natural resources, unique structural features and the most relevant biological properties of proline-rich peptides of marine-origin, focusing on the potential therapeutic role that the PRCPs may play as a promising source of new peptide-based novel drugs.

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          Marine natural products as anticancer drugs.

          The chemical and biological diversity of the marine environment is immeasurable and therefore is an extraordinary resource for the discovery of new anticancer drugs. Recent technological and methodologic advances in structure elucidation, organic synthesis, and biological assay have resulted in the isolation and clinical evaluation of various novel anticancer agents. These compounds range in structural class from simple linear peptides, such as dolastatin 10, to complex macrocyclic polyethers, such as halichondrin B; equally as diverse are the molecular modes of action by which these molecules impart their biological activity. This review highlights several marine natural products and their synthetic derivatives that are currently undergoing clinical evaluation as anticancer drugs.
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            Proline cis-trans isomerization and protein folding.

            Proline cis-trans isomerization plays a key role in the rate-determining steps of protein folding. The energetic origin of this isomerization process is summarized, and the folding and unfolding of disulfide-intact bovine pancreatic ribonuclease A is used as an example to illustrate the kinetics and structural features of conformational changes from the heterogeneous unfolded state (consisting of cis and trans isomers of X-Pro peptide groups) to the native structure in which only one set of proline isomers is present.
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              Peptides and Peptidomimetics for Antimicrobial Drug Design

              The purpose of this paper is to introduce and highlight a few classes of traditional antimicrobial peptides with a focus on structure-activity relationship studies. After first dissecting the important physiochemical properties that influence the antimicrobial and toxic properties of antimicrobial peptides, the contributions of individual amino acids with respect to the peptides antibacterial properties are presented. A brief discussion of the mechanisms of action of different antimicrobials as well as the development of bacterial resistance towards antimicrobial peptides follows. Finally, current efforts on novel design strategies and peptidomimetics are introduced to illustrate the importance of antimicrobial peptide research in the development of future antibiotics.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Mar Drugs
                Mar Drugs
                marinedrugs
                Marine Drugs
                MDPI
                1660-3397
                26 October 2016
                November 2016
                : 14
                : 11
                : 194
                Affiliations
                [1 ]School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China; wanyinfang@ 123456whut.edu.cn
                [2 ]Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, Saint Augustine, Trinidad and Tobago, West Indies; Sandeep.Maharaj@ 123456sta.uwi.edu
                [3 ]School of Pharmacy, College of Medicine and Health Sciences, University of Gondar, Gondar 196, Ethiopia; ritz_pharma@ 123456yahoo.co.in
                Author notes
                [* ]Correspondence: Rajiv.Dahiya@ 123456sta.uwi.edu (R.D.); qinhuali@ 123456whut.edu.cn (H.-L.Q.); Tel.: +1868-493-5655 (R.D.); +86-27-8774-9379 (H.-L.Q.)
                [†]

                These authors contribute equally to this work.

                Article
                marinedrugs-14-00194
                10.3390/md14110194
                5128737
                27792168
                f89396fa-dc97-4fcd-bcb7-cb49ff192ee1
                © 2016 by the authors; licensee MDPI, Basel, Switzerland.

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 11 September 2016
                : 15 October 2016
                Categories
                Review

                Pharmacology & Pharmaceutical medicine
                proline-rich cyclic peptide,marine sponge,marine tunicate,peptide synthesis,stereochemistry,lipophilicity parameter,pharmacological activity

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