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Chiral lipidic dialkynylcarbinols (DACs), recently highlighted as antitumoral pharmacophores, have been conjugated to difluoroboron-dipyrromethene (bodipy), 7-hydroxy-coumarine, and 7-nitro-benzoxadiazole (NBD) fluorophore motifs through triazole clips. The labeled lipids preserve cytotoxic activity against HCT116 cells, and fluorescence microscopy of the stained cells showed clear signals in the intra-cellular membrane system. While the bodipy conjugate also labels lipid droplets very brightly, as expected, the coumarine and NBD probes appear as promising specific tools for the identification of the intra-cellular targets of DACs' cytotoxicity.
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http://dx.doi.org/10.1016/j.bmcl.2015.08.029 | DOI Listing |
J Am Chem Soc
September 2025
Laboratory for Fundamental BioPhotonics (LBP), Institute of Bioengineering (IBI), School of Engineering (STI), École Polytechnique Fédérale de Lausanne (EPFL), Lausanne CH-1015, Switzerland.
Life requires chemical chiral specificity. The emergence of enantioselectivity is unknown but has been linked to diverse scenarios for the origin of life, ranging from an extraterrestrial origin to polarization-induced effects, and magnetic field-induced mineral templating. These scenarios require an originating mechanism and a subsequent enhancement step, leading to widespread chiral specificity.
View Article and Find Full Text PDFSci Rep
August 2025
School of Pharmacy and Medical Technology, Putian University, Putian, 351100, China.
The total synthesis of compound 1, a chiral diglyceride metabolite present in both humans and fungi, was achieved via a seven-step route, affording the target molecule in 2.33% overall yield. The synthetic strategy involved: (1) selective protection of the terminal hydroxyl group of chiral ketal 2 with a sterically hindered benzyl group, followed by ketal deprotection to yield benzyl ether 4; (2) protection of the terminal hydroxyl group of benzyl ether 4 with a bulky silyl protecting group, and subsequent esterification of the remaining hydroxyl with erucic acid to generate ester 6; (3) removal of the silyl protecting group from ester 6, followed by esterification of the liberated hydroxyl group with pentadecanoic acid to afford ester 8; and (4) selective deprotection of the benzyl group of ester 8 to furnish compound 1.
View Article and Find Full Text PDFTop Curr Chem (Cham)
August 2025
College of Chemical Engineering, Department of Pharmaceutical Engineering, Northwest University, 1 Xuefu Road, Xi'an, 710127, China.
Phytosphingosine, a type of sphingolipids, has gained significant attention due to their diverse biological activities, including anti-inflammatory, anticancer, and immunomodulatory properties. These bioactive lipids, predominantly found in plant sources, play crucial roles in cellular signaling and membrane structure. In recent years, the chemical synthesis of phytosphingosine and other sphingolipids have become a major focus in organic chemistry due to the increasing demand for these molecules in pharmacological research and drug development.
View Article and Find Full Text PDFAppl Environ Microbiol
August 2025
Department of Plant and Microbial Biology, North Carolina State University, Raleigh, North Carolina, USA.
Isobutylene (IB) is produced on a large scale by the petrochemical industry and is metabolized by the aerobic alkene-metabolizing bacterium sp. ELW1. The initial metabolite of IB catabolism by this bacterium is proposed to be 2-methyl-1,2-epoxypropane (isobutylene oxide [IBO]).
View Article and Find Full Text PDFChemistry
August 2025
Institut des Biomolécules Max Mousseron, IBMM, Univ. Montpellier, CNRS, ENSCM, 1919 route de Mende, Montpellier, 34293, France.
Neuroprostanes (NeuroPs) are bioactive oxylipins formed in vivo from docosahexaenoic acid (DHA), the main polyunsaturated fatty acid of the human brain, by a nonenzymatic auto-oxidative process as mixtures of regio- and diastereoisomers. Thus, synthetic material is necessary to unlock their potential as oxidative stress biomarkers as well as to investigate the biological properties of individual NeuroP molecules. Despite recent advances in the field, cyclopentenone-type NeuroPs have received limited attention.
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