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Synthesis and Toxicology of p ‐Phosphonic Acid Calixarenes and O‐Alkylated Analogues as Potential Calixarene‐Based Phospholipids
Author(s) -
Martin Adam D.,
Houlihan Emma,
Morellini Natalie,
Eggers Paul K.,
James Eliza,
Stubbs Keith A.,
Harvey Alan R.,
Fitzgerald Melinda,
Raston Colin L.,
Dunlop Sarah A.
Publication year - 2012
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201100081
Subject(s) - calixarene , alkylation , chemistry , micelle , curcumin , alkyl , stereochemistry , in vitro , aqueous solution , organic chemistry , biochemistry , molecule , catalysis
A series of p ‐phosphonic acid calix[ n ]arenes 1 a–g bearing hydroxy groups, n =4 and 5, or alkyl chains of varying lengths at their lower rim, n =4, were synthesised, and in vitro assessments of their effect on cell viability in rat PC12 cells and primary cultures of mixed retinal cells were conducted. Compounds 1 a and 1 g , bearing hydroxy groups at their lower rim, displayed lower toxicity towards PC12 cells than their alkylated counterparts; concentrations of up to 1 mg mL −1 did not affect the number of viable cells. Mixed retinal cultures showed a higher susceptibility towards toxic effects for all calixarenes tested. Compound 1 b self‐assembles into nanofibres from a toluene solution, and 1 c assembles into micelles from an aqueous solution, with these nanoscale architectures showing potential applications for various biological roles, such as solubilising p‐ nitrophenol and curcumin.