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Special Issue "Marine Organohalides"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 August 2016)

Special Issue Editor

Guest Editor
Dr. Miguel O. Mitchell

American Institutes for Research, 1000 Thomas Jefferson St NW, Washington, DC 20007, USA
Website | E-Mail
Interests: antibacterial agents; cation-pi and sigma hole-based protein–ligand complex investigations; the interface of chemistry and art; improving low-income accessibility of hands-on chemical instrumentation-based experiments in analytical chemistry and biochemistry

Special Issue Information

Dear Colleagues,

This Special Issue will encompass research pertaining to halogenated marine natural products, their biosynthesis, total synthesis, biological and pharmacological profiles, and halogen bonding to receptors. Articles submitted may be full research papers or reviews covering the past five years (2010–2015). Full research papers claiming to have ascertained molecular structures of natural products or intermediates and final products in the total synthesis of natural products must at a minimum provide IR spectra, proton and carbon NMR spectra, and HRMS as supporting data; HMBC and NOESY specta may be required for compounds of sufficient stereochemical complexity. Syntheses must also contain as supplement detailed, experimental procedures, including isolated yields.

Prof. Dr. Miguel O. Mitchell
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. Marine Drugs 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

  • halogenated
  • marine
  • natural product
  • biosynthesis
  • halogen bonding
  • pharmacology
  • synthesis
  • receptor binding

Published Papers (4 papers)

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Research

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Open AccessArticle Determination of the Halogenated Skeleton Constituents of the Marine Demosponge Ianthella basta
Mar. Drugs 2017, 15(2), 34; doi:10.3390/md15020034
Received: 10 October 2016 / Revised: 19 January 2017 / Accepted: 3 February 2017 / Published: 10 February 2017
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Abstract
Demosponges of the order Verongida such as Ianthella basta exhibit skeletons containing spongin, a collagenous protein, and chitin. Moreover, Verongida sponges are well known to produce bioactive brominated tyrosine derivatives. We recently demonstrated that brominated compounds do not only occur in the cellular
[...] Read more.
Demosponges of the order Verongida such as Ianthella basta exhibit skeletons containing spongin, a collagenous protein, and chitin. Moreover, Verongida sponges are well known to produce bioactive brominated tyrosine derivatives. We recently demonstrated that brominated compounds do not only occur in the cellular matrix but also in the skeletons of the marine sponges Aplysina cavernicola and I. basta. Further investigations revealed the amino acid composition of the skeletons of A. cavernicola including the presence of several halogenated amino acids. In the present work, we investigated the skeletal amino acid composition of the demosponge I. basta, which belongs to the Ianthellidae family, and compared it with that of A. cavernicola from the Aplysinidae family. Seventeen proteinogenic and five non-proteinogenic amino acids were detected in I. basta. Abundantly occurring amino acids like glycine and hydroxyproline show the similarity of I. basta and A. cavernicola and confirm the collagenous nature of their sponging fibers. We also detected nine halogenated tyrosines as an integral part of I. basta skeletons. Since both sponges contain a broad variety of halogenated amino acids, this seems to be characteristic for Verongida sponges. The observed differences of the amino acid composition confirm that spongin exhibits a certain degree of variability even among the members of the order Verongida. Full article
(This article belongs to the Special Issue Marine Organohalides)
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Open AccessArticle The Sequestration of Oxy-Polybrominated Diphenyl Ethers in the Nudibranchs Miamira magnifica and Miamira miamirana
Mar. Drugs 2016, 14(11), 198; doi:10.3390/md14110198
Received: 25 August 2016 / Revised: 16 October 2016 / Accepted: 18 October 2016 / Published: 27 October 2016
PDF Full-text (760 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of oxy-polybrominated diphenyl ethers (O-PBDEs) has been isolated from the extracts of Miamira magnifica and Miamira miamirana collected from Queensland, Australia. M. magnifica sequesters the new OH-PBDE 1 and six known OH-PBDEs containing four to six bromines (27
[...] Read more.
A series of oxy-polybrominated diphenyl ethers (O-PBDEs) has been isolated from the extracts of Miamira magnifica and Miamira miamirana collected from Queensland, Australia. M. magnifica sequesters the new OH-PBDE 1 and six known OH-PBDEs containing four to six bromines (27). M. miamirana also accumulates known tribromo- and tetrabromo OMe-PBDEs 810 in both mantle and viscera tissues. To date, Miamira is the only genus of the family Chromodorididae that is known to incorporate O-PBDEs, rather than terpenes, in the mantle where the metabolites may play a putative role in chemical defense. The extract of M. magnifica was tested in a brine shrimp lethality assay and exhibited an LD50 of 58 μg/mL. Full article
(This article belongs to the Special Issue Marine Organohalides)
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Figure 1

Open AccessArticle MDN-0170, a New Napyradiomycin from Streptomyces sp. Strain CA-271078
Mar. Drugs 2016, 14(10), 188; doi:10.3390/md14100188
Received: 11 August 2016 / Revised: 29 September 2016 / Accepted: 13 October 2016 / Published: 18 October 2016
Cited by 1 | PDF Full-text (1392 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new napyradiomycin, MDN-0170 (1), was isolated from the culture broth of the marine-derived actinomycete strain CA-271078, together with three known related compounds identified as 4-dehydro-4a-dechloronapyradiomycin A1 (2), napyradiomycin A1 (3) and 3-chloro-6,8-dihydroxy-8-α-lapachone (4). The
[...] Read more.
A new napyradiomycin, MDN-0170 (1), was isolated from the culture broth of the marine-derived actinomycete strain CA-271078, together with three known related compounds identified as 4-dehydro-4a-dechloronapyradiomycin A1 (2), napyradiomycin A1 (3) and 3-chloro-6,8-dihydroxy-8-α-lapachone (4). The structure of the new compound was determined using a combination of spectroscopic techniques, including 1D and 2D NMR and electrospray-time of flight mass spectrometry (ESI-TOF MS). The relative configuration of compound 1, which contains two independent stereoclusters, has been established by molecular modelling in combination with nOe and coupling constant analyses. Biosynthetic arguments also allowed us to propose its absolute stereochemistry. The antimicrobial properties of the compounds isolated were evaluated against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, Aspergillus fumigatus, and Candida albicans. The potent bioactivity previously reported for compounds 2 and 3 against methicillin-sensitive S. aureus has been extended to methicillin-resistant strains in this report. Full article
(This article belongs to the Special Issue Marine Organohalides)
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Review

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Open AccessReview Chiral Alkyl Halides: Underexplored Motifs in Medicine
Mar. Drugs 2016, 14(11), 206; doi:10.3390/md14110206
Received: 24 September 2016 / Revised: 21 October 2016 / Accepted: 31 October 2016 / Published: 4 November 2016
Cited by 2 | PDF Full-text (2501 KB) | HTML Full-text | XML Full-text
Abstract
While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems.
[...] Read more.
While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems. A number of chlorinated compounds in the pharmaceutical and food industries, as well as a growing number of halogenated marine natural products showing unique bioactivity, illustrate the role that chiral alkyl halides can play in drug discovery. Through a series of case studies, we demonstrate in this review that these motifs can indeed be stable under physiological conditions, and that halogenation can enhance bioactivity through both steric and electronic effects. Our hope is that, by placing such compounds in the minds of the chemical community, they may gain more traction in drug discovery and inspire more synthetic chemists to develop methods for selective halogenation. Full article
(This article belongs to the Special Issue Marine Organohalides)
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Figure 1

Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Polybrominated diphenyl ethers (PBDE) revisited: Evidence of the sequestration of PBDE in nudibranch
Authors: Ariyanti S. Dewi 1, Holly E. Urquhart 2, Karen L. Cheney 2, Mary J. Garson 1
Affiliations: 1 School of Chemistry and Molecula Biosciences, University of Queensland, Australia; 2 School of Biological Sciences, University of Queensland, Australia
Abstract: Investigation of the chemistry of the Chromodorid nudibranch, Miamira magnifica is described for the first time. A series of polybrominated diphenyl ethers has been isolated from the extracts of M. magnifica collected in North Stradbroke Island, Australia. A new compound, namely 1-hydroxy-3,4,2’,4’-tetrabromodiphenyl ether, was isolated from the mantle and digestive tissues of the nudibranch. There is an evidence that M. magnifica selectively incorporate tetrabromo- and pentabromo diphenyl ethers in the mantle—but not hexabromo diphenylether—from the sponge diet. The extract of M. miamira was tested in a brine shrimp lethality assay and exhibited a strong activity with an LD50 of 0.05 mg/mL.

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