Marine Metabolites

Gallimore, Winklet A.

doi:10.1016/b978-0-12-802104-0.00018-4

Cited by 14 publications

(5 citation statements)

References 82 publications

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“…Encouraged by the applicability of our mild conditions in derivatizing relatively complex halogenated molecules containing sensitive functionalities, we explored their application as a method of late-stage functionalization for halogenated natural products. Marine metabolites have evolved to perform a series of roles, especially in signaling inter and intra species . Produced in the oceans, where they could be readily washed away, certain metabolites are often highly lipophilic, , potentially promoting their uptake and retention within various biological systems.…”

Section: Resultsmentioning

confidence: 99%

“…Marine metabolites have evolved to perform a series of roles, especially in signaling inter and intra species. 47 Produced in the oceans, where they could be readily washed away, certain metabolites are often highly lipophilic, 48 , 49 potentially promoting their uptake and retention within various biological systems. Their interplay between organic and aqueous environments is critical, and the possibility to tag and track or immobilize these metabolites has the potential to open new horizons in the chemical ecology.…”

Section: Resultsmentioning

confidence: 99%

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Fully Aqueous and Air-Compatible Cross-Coupling of Primary Alkyl Halides with Aryl Boronic Species: A Possible and Facile Method

Molyneux

Goss

2023

ACS Catal.

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Aqueous transformations confer many advantages, including decreased environmental impact and increased opportunity for biomolecule modulation. Although several studies have been conducted to enable the cross-coupling of aryl halides in aqueous conditions, until now a process for the cross-coupling of primary alkyl halides in aqueous conditions was missing from the catalytic toolbox and considered impossible. Alkyl halide coupling in water suffers from severe problems. The reasons for this include the strong propensity for β-hydride elimination, the need for highly air-and water-sensitive catalysts and reagents, and the intolerance of many hydrophilic groups to cross-coupling conditions. Here, we report a broadly applicable and readily accessible process for the cross-coupling of water-soluble alkyl halides in water and air by using simple and commercially available bench-stable reagents. The trisulfonated aryl phosphine TXPTS in combination with a water-soluble palladium salt Na 2 PdCl 4 allowed for the Suzuki−Miyaura coupling of water-soluble alkyl halides with aryl boronic acids, boronic esters, and borofluorate salts in mild, fully aqueous conditions. Multiple challenging functionalities, including unprotected amino acids, an unnatural halogenated amino acid within a peptide, and herbicides can be diversified in water. Structurally complex natural products were used as testbeds to showcase the late-stage tagging methodology of marine natural products to enable liquid chromatography−mass spectrometry (LC−MS) detection. This enabling methodology therefore provides a general method for the environmentally friendly and biocompatible derivatization of sp 3 alkyl halide bonds.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Fully Aqueous and Air-Compatible Cross-Coupling of Primary Alkyl Halides with Aryl Boronic Species: A Possible and Facile Method

Molyneux

Goss

2023

ACS Catal.

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“…Mycalamides A and B, protein synthesis inhibitors and antiviral compounds isolated from a sponge Mycale incrustans Burton, also inhibited coronavirus A59 (Laport et al 2009). In vivo activity against coronavirus A59 was observed in mice treated with a 2% mycalamide mixture at a dosage of 0.2 μg/kg daily with 100% survival over a 2-week period (Gallimore 2017). Triterpenes (thyrsiferol, thyrsiferol acetate, venustatriol) isolated from the red alga Laurencia venusta Yamada inhibit coronaviruses, and orthosterol disodium sulfates from the sponge Petrosia weinbergi Van Soest inhibit coronavirus A59 (El Sayed 2000).…”

Section: Marine Algae and Spongesmentioning

confidence: 97%

Coronaviruses and Nature’s Pharmacy for the Relief of Coronavirus Disease 2019

Chinsembu

2020

Rev. Bras. Farmacogn.

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Current challenges to the treatment of coronavirus disease 2019 should open new prospects in the search for novel drugs from medicinal plants and other natural products. This paper provides details of natural agents that inhibit human coronavirus entry into cells, general replication, and specific chymotrypsin-like protease (3CL pro)-mediated replication. Medicinal plants, fungi, and marine organisms as remedies for human coronaviruses in China, Lebanon, Malaysia, Singapore, and South Africa are described. Common species include Alnus japonica (Thunb.

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“…For several decades, virtual screening has been used to identify the best lead compounds with a range of structural features for usage with a specific biological target [ 15 ]. Furthermore, computer-aided drug design has been used to identify, validate and explore various biological properties of marine metabolites including anti-inflammatory, anti-infectious, anti-cancer, antiviral, and anti-microbial effects via virtual screening, molecular docking, and dynamics modelling [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%