Cyclic hydroxamic acids are innate compounds associated with pest resistance in several grass species. The major cyclic hydroxamic acids of com, 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-3H-1,4-benzoxazin-3-one (DIBOA), were measured in seedlings after exposure to various water stress treatments. Both DIMBOA and DIBOA were found in greater quantities in plants experiencing a water deficit stress than in nonstressed plants. The increased cyclic hydroxamic acid coincided with a reduction in seedling growth, suggesting that cyclic hydroxamic acids are stress metabolites. Plants grown under conditions that restrict growth, such as water deficit stress, contain higher cyclic hydroxamic acids, which should make them more resistant to herbivorous pests and pathogenic microorganisms.
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http://dx.doi.org/10.1007/BF00982296 | DOI Listing |
Invest Ophthalmol Vis Sci
January 2025
Department of Ophthalmology, Duke Eye Center, Duke University, Durham, North Carolina, United States.
Purpose: To study the roles of tubulin acetylation and cyclic mechanical stretch (CMS) in trabecular meshwork (TM) cells and their impact on outflow pathway physiology and pathology.
Methods: Primary TM cell cultures were subjected to CMS (8% elongation, 24 hours), and acetylated α-tubulin at lysine 40 (Ac-TUBA4) was assessed by western blotting and immunofluorescence. Enzymes regulating tubulin acetylation were identified via siRNA-mediated knockdowns of ATAT1, HDAC6, and SIRT2.
Mar Drugs
October 2024
Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia.
The first total synthesis of the Australian marine tunicate fungus-derived cyclic peptide talarolide A () has confirmed the structure previously proposed on the basis of spectroscopic and chemical analyses and re-affirmed the importance of the unique hydroxamate H-bond bridge in ring conformer stabilization. The unexpected co-synthesis of -talarolide A () revealed, for the first time, that hydroxamate H-bond bridging in the talarolide framework invokes non-canonical atropisomerism and that talarolides A (), C (), and D () all exist naturally as atropisomers. These discoveries raise the intriguing prospect that comparable functionalisation of other cyclic peptides, including those with commercial value, could provide ready access to new "unnatural atropisomeric" chemical space, with new and/or improved chemical and biological properties.
View Article and Find Full Text PDFJ Org Chem
July 2024
Department of Chemistry, UNC College of Arts and Sciences, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
Bifunctional thiourea-based organocatalysts facilitate an enantioselective desymmetrization and Lossen rearrangement cascade reaction of -sulfoxy -succinimides, resulting in the synthesis of cyclic β-amino acid derivatives. This catalytic system was optimized for bicyclic and tricyclic succinimide substrates affording yields from 61-91% and up to 96:4 er. This reaction proceeds via the group selective addition of the primary alcohol nucleophile to an enantiotopic carbonyl group with sequential rearrangement of the intermediate -sulfonyl hydroxamate ester.
View Article and Find Full Text PDFChem Commun (Camb)
July 2024
Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2,4-4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method was demonstrated on a gram-scale.
View Article and Find Full Text PDFChemistry
August 2024
School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, 1142, New Zealand.
The clinical use of many potent anticancer agents is limited by their non-selective toxicity to healthy tissue. One of these examples is vorinostat (SAHA), a pan histone deacetylase inhibitor, which shows high cytotoxicity with limited discrimination for cancerous over healthy cells. In an attempt to improve tumor selectivity, we exploited the properties of cobalt(III) as a redox-active metal center through stabilization with cyclen and cyclam tetraazamacrocycles, masking the anticancer activity of SAHA and other hydroxamic acid derivatives to allow for the complex to reach the hypoxic microenvironment of the tumor.
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