FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2904201130> ?p ?o ?g. }

• W2904201130 endingPage "583" @default.
• W2904201130 startingPage "573" @default.
• W2904201130 abstract "Boron containing polyhedra (carboranes) are three-dimensional delocalized aromatic systems. These structures have been shown to transport protons through lipid membranes and mitochondria. Conjugation of carboranes to various organic moieties is aimed at obtaining biologically active compounds with novel properties. Taking advantage of 1,2,3-triazoles as the scaffolds valuable in medicinal chemistry, we synthesized 1-(o-carboranylmethyl)-4-pentyl-1,2,3-triazole (c-triazole) and 1-(o-carboranylmethyl)-4-pentyl-1,2,3-triazolium iodide (c-triazolium). Both compounds interacted with model lipid membranes and exhibited a proton carrying activity in planar bilayers and liposomes in a concentration- and pH-dependent manner. Importantly, mechanisms of the protonophoric activity differed; namely, protonation-deprotonation reactions of the triazole and the o-carborane moieties were involved in the transport cycles of c-triazole and c-triazolium, respectively. At micromolar concentrations, c-triazole and c-triazolium stimulated respiration of isolated rat liver mitochondria and depolarized their membrane potential, with c-triazole being more potent. In living K562 (human chronic myelogenous leukemia) cells, both c-triazolium and c-triazole altered the mitochondrial membrane potential as determined by a decreased intracellular accumulation of the potential-dependent dye tetramethylrhodamine ethyl ester. Finally, cell viability testing demonstrated a cytotoxic potency of c-triazolium and, to a lesser extent, of c-triazole against K562 cells, whereas non-malignant fibroblasts were much less sensitive. In all tests, the reference boron-free benzyl-4-pentyl-1,2,3-triazole showed little-to-no effects. These results demonstrated that carboranyltriazoles carry protons across biological membranes, a property potentially important in anticancer drug design." @default.
• W2904201130 created "2018-12-22" @default.
• W2904201130 creator A5008481478 @default.
• W2904201130 creator A5022297907 @default.
• W2904201130 creator A5031442723 @default.
• W2904201130 creator A5045616453 @default.
• W2904201130 creator A5046033665 @default.
• W2904201130 creator A5051907923 @default.
• W2904201130 creator A5056155641 @default.
• W2904201130 creator A5068442652 @default.
• W2904201130 date "2019-03-01" @default.
• W2904201130 modified "2023-10-12" @default.
• W2904201130 title "Carborane derivatives of 1,2,3-triazole depolarize mitochondria by transferring protons through the lipid part of membranes" @default.
• W2904201130 cites W12343461 @default.
• W2904201130 cites W1490847753 @default.
• W2904201130 cites W1702491069 @default.
• W2904201130 cites W1812701728 @default.
• W2904201130 cites W1913353793 @default.
• W2904201130 cites W1964462507 @default.
• W2904201130 cites W1970881583 @default.
• W2904201130 cites W1972206172 @default.
• W2904201130 cites W1974677595 @default.
• W2904201130 cites W1980963182 @default.
• W2904201130 cites W1982334965 @default.
• W2904201130 cites W2002193947 @default.
• W2904201130 cites W2005037614 @default.
• W2904201130 cites W2006258627 @default.
• W2904201130 cites W2008486832 @default.
• W2904201130 cites W2014871571 @default.
• W2904201130 cites W2017004251 @default.
• W2904201130 cites W2021521297 @default.
• W2904201130 cites W2023046868 @default.
• W2904201130 cites W2029135335 @default.
• W2904201130 cites W2031447511 @default.
• W2904201130 cites W2043907233 @default.
• W2904201130 cites W2045597552 @default.
• W2904201130 cites W2045838525 @default.
• W2904201130 cites W2050995010 @default.
• W2904201130 cites W2064417516 @default.
• W2904201130 cites W2067529763 @default.
• W2904201130 cites W2068973847 @default.
• W2904201130 cites W2086198406 @default.
• W2904201130 cites W2088363546 @default.
• W2904201130 cites W2095229391 @default.
• W2904201130 cites W2111428753 @default.
• W2904201130 cites W2114388515 @default.
• W2904201130 cites W2121811699 @default.
• W2904201130 cites W2122608594 @default.
• W2904201130 cites W2122691360 @default.
• W2904201130 cites W2124952091 @default.
• W2904201130 cites W2127232885 @default.
• W2904201130 cites W2134595594 @default.
• W2904201130 cites W2142519216 @default.
• W2904201130 cites W2149434199 @default.
• W2904201130 cites W2164180767 @default.
• W2904201130 cites W2167601866 @default.
• W2904201130 cites W2191832297 @default.
• W2904201130 cites W2250820623 @default.
• W2904201130 cites W2275525580 @default.
• W2904201130 cites W2291903346 @default.
• W2904201130 cites W2342204273 @default.
• W2904201130 cites W2344037737 @default.
• W2904201130 cites W2345663368 @default.
• W2904201130 cites W2416416701 @default.
• W2904201130 cites W2418897773 @default.
• W2904201130 cites W2606333923 @default.
• W2904201130 cites W2607409185 @default.
• W2904201130 cites W2767100805 @default.
• W2904201130 cites W2771028705 @default.
• W2904201130 cites W2793431601 @default.
• W2904201130 cites W947635323 @default.
• W2904201130 doi "https://doi.org/10.1016/j.bbamem.2018.12.009" @default.
• W2904201130 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30562498" @default.
• W2904201130 hasPublicationYear "2019" @default.
• W2904201130 type Work @default.
• W2904201130 sameAs 2904201130 @default.
• W2904201130 citedByCount "17" @default.
• W2904201130 countsByYear W29042011302019 @default.
• W2904201130 countsByYear W29042011302020 @default.
• W2904201130 countsByYear W29042011302021 @default.
• W2904201130 countsByYear W29042011302022 @default.
• W2904201130 countsByYear W29042011302023 @default.
• W2904201130 crossrefType "journal-article" @default.
• W2904201130 hasAuthorship W2904201130A5008481478 @default.
• W2904201130 hasAuthorship W2904201130A5022297907 @default.
• W2904201130 hasAuthorship W2904201130A5031442723 @default.
• W2904201130 hasAuthorship W2904201130A5045616453 @default.
• W2904201130 hasAuthorship W2904201130A5046033665 @default.
• W2904201130 hasAuthorship W2904201130A5051907923 @default.
• W2904201130 hasAuthorship W2904201130A5056155641 @default.
• W2904201130 hasAuthorship W2904201130A5068442652 @default.
• W2904201130 hasConcept C12554922 @default.
• W2904201130 hasConcept C145148216 @default.
• W2904201130 hasConcept C1491633281 @default.
• W2904201130 hasConcept C171122931 @default.
• W2904201130 hasConcept C178790620 @default.
• W2904201130 hasConcept C181911157 @default.
• W2904201130 hasConcept C185592680 @default.

• next