Matches in SemOpenAlex for { <https://semopenalex.org/work/W1966536447> ?p ?o ?g. }
- W1966536447 endingPage "2422" @default.
- W1966536447 startingPage "2413" @default.
- W1966536447 abstract "We report the synthesis and X-ray crystal structures of three acyclic CB[n]-type molecular containers (2a, 2h, 2f) that differ in the charge on their solubilizing groups (SO3(−), OH, NH3(+)). The X-ray crystal structures of compounds 2h and 2f reveal a self-folding of the ArOCH2CH2X wall into the cavity driven by π–π interactions, H-bonds and ion–dipole interactions. The need to reverse this self-folding phenomenon upon guest binding decreases the affinity of 2h and 2f toward cationic guests in water relative to 2a as revealed by direct (1)H NMR and UV/Vis titrations as well as UV/Vis competition experiments. We determined the pKa of 6-aminocoumarin 7 (pKa = 3.6) on its own and in the presence anionic, neutral, and cationic hosts (2a: pKa = 4.9; 2h: pKa = 4.1; 2f, pKa = 3.4) which reflect in part the relevance of direct ion–ion interactions between the arms of the host and the guest toward the recognition properties of acyclic CB[n]-type containers. Finally, we showed that the weaker binding affinities measured for neutral and positively charged hosts 2h and 2f compared to anionic 2a results in a decreased ability to act as solubilizing agents for either cationic (tamoxifen), neutral (17α-ethynylestradiol), or anionic (indomethacin) drugs in water. The results establish that acyclic CB[n] compounds that bear anionic solubilizing groups are most suitable for development as general purpose solubilizing excipients for insoluble pharmaceutical agents." @default.
- W1966536447 created "2016-06-24" @default.
- W1966536447 creator A5031106218 @default.
- W1966536447 creator A5049280385 @default.
- W1966536447 creator A5068678304 @default.
- W1966536447 date "2014-01-01" @default.
- W1966536447 modified "2023-09-30" @default.
- W1966536447 title "Acyclic CB[n]-type molecular containers: effect of solubilizing group on their function as solubilizing excipients" @default.
- W1966536447 cites W1965122895 @default.
- W1966536447 cites W1976723967 @default.
- W1966536447 cites W1978713499 @default.
- W1966536447 cites W1978926557 @default.
- W1966536447 cites W1979657535 @default.
- W1966536447 cites W1981019220 @default.
- W1966536447 cites W1982810365 @default.
- W1966536447 cites W1983344857 @default.
- W1966536447 cites W1983899252 @default.
- W1966536447 cites W1987252409 @default.
- W1966536447 cites W1988733774 @default.
- W1966536447 cites W1992434579 @default.
- W1966536447 cites W1994384674 @default.
- W1966536447 cites W1995008519 @default.
- W1966536447 cites W1997260045 @default.
- W1966536447 cites W1997502039 @default.
- W1966536447 cites W2000513559 @default.
- W1966536447 cites W2004253819 @default.
- W1966536447 cites W2004590198 @default.
- W1966536447 cites W2006011959 @default.
- W1966536447 cites W2006568020 @default.
- W1966536447 cites W2007499283 @default.
- W1966536447 cites W2016144279 @default.
- W1966536447 cites W2017108099 @default.
- W1966536447 cites W2017871235 @default.
- W1966536447 cites W2020337784 @default.
- W1966536447 cites W2021891281 @default.
- W1966536447 cites W2022148362 @default.
- W1966536447 cites W2025688309 @default.
- W1966536447 cites W2026085713 @default.
- W1966536447 cites W2026562094 @default.
- W1966536447 cites W2028794342 @default.
- W1966536447 cites W2029611399 @default.
- W1966536447 cites W2033560751 @default.
- W1966536447 cites W2034961303 @default.
- W1966536447 cites W2039104539 @default.
- W1966536447 cites W2040437294 @default.
- W1966536447 cites W2044578454 @default.
- W1966536447 cites W2044594845 @default.
- W1966536447 cites W2048987916 @default.
- W1966536447 cites W2052384642 @default.
- W1966536447 cites W2054125712 @default.
- W1966536447 cites W2056434768 @default.
- W1966536447 cites W2057940109 @default.
- W1966536447 cites W2061119072 @default.
- W1966536447 cites W2067841092 @default.
- W1966536447 cites W2068017438 @default.
- W1966536447 cites W2069506489 @default.
- W1966536447 cites W2069635793 @default.
- W1966536447 cites W2074984060 @default.
- W1966536447 cites W2077534391 @default.
- W1966536447 cites W2087571702 @default.
- W1966536447 cites W2088252867 @default.
- W1966536447 cites W2089260204 @default.
- W1966536447 cites W2091068412 @default.
- W1966536447 cites W2095422424 @default.
- W1966536447 cites W2099677859 @default.
- W1966536447 cites W2101479143 @default.
- W1966536447 cites W2106346416 @default.
- W1966536447 cites W2117508948 @default.
- W1966536447 cites W2119418976 @default.
- W1966536447 cites W2124860710 @default.
- W1966536447 cites W2124905988 @default.
- W1966536447 cites W2131910659 @default.
- W1966536447 cites W2133297073 @default.
- W1966536447 cites W2135129422 @default.
- W1966536447 cites W2136284957 @default.
- W1966536447 cites W2139902274 @default.
- W1966536447 cites W2144901490 @default.
- W1966536447 cites W2145010618 @default.
- W1966536447 cites W2145271930 @default.
- W1966536447 cites W215025240 @default.
- W1966536447 cites W2152380893 @default.
- W1966536447 cites W2160134664 @default.
- W1966536447 cites W2161030462 @default.
- W1966536447 cites W2162250373 @default.
- W1966536447 cites W2163153095 @default.
- W1966536447 cites W2164227888 @default.
- W1966536447 cites W2164283535 @default.
- W1966536447 cites W2166414534 @default.
- W1966536447 cites W2169594520 @default.
- W1966536447 cites W2173353533 @default.
- W1966536447 cites W2318316507 @default.
- W1966536447 cites W2809722643 @default.
- W1966536447 cites W2952528349 @default.
- W1966536447 cites W4243838097 @default.
- W1966536447 doi "https://doi.org/10.1039/c3ob42603c" @default.
- W1966536447 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4035228" @default.
- W1966536447 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24595500" @default.
- W1966536447 hasPublicationYear "2014" @default.