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DNA Recognition with Polycyclic‐Aromatic‐Hydrocarbon‐Presenting Calixarene Conjugates
Author(s) -
Rescifina Antonio,
Zagni Chiara,
Mineo Placido G.,
Giofrè Salvatore V.,
Chiacchio Ugo,
Tommasone Stefano,
Talotta Carmen,
Gaeta Carmine,
Neri Placido
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403050
Subject(s) - chemistry , calixarene , circular dichroism , dna , intercalation (chemistry) , stereochemistry , conjugate , polycyclic aromatic hydrocarbon , porphyrin , combinatorial chemistry , organic chemistry , molecule , biochemistry , mathematical analysis , mathematics
New calix[4]arene conjugates that present polycyclic aromatic hydrocarbons (PAHs) at their exo rims have been synthesized by esterification of a cone‐shaped calix[4]arenedicarboxylic acid with trans ‐ or cis ‐pyrenylisoxazolidinyl alcohols prepared by a 1,3‐dipolar cycloaddition methodology. The in vitro cytotoxic activities of all compounds were evaluated with three different human tumor cell lines, and the most potent one reached an IC 50 of 95 n M . The different biological activities of the synthesized compounds were explained by docking and circular dichroism studies, which evidenced their intercalating abilities from the DNA minor groove.