DNA Recognition with Polycyclic‐Aromatic‐Hydrocarbon‐Presenting Calixarene Conjugates1. Issue 34 (21st October 2014)

• Record Type: Journal Article
• Authors: Rescifina, Antonio; Zagni, Chiara; Mineo, Placido G.; Giofrè, Salvatore V.; Chiacchio, Ugo; Tommasone, Stefano; Talotta, Carmen; Gaeta, Carmine; Neri, Placido
• Is Part Of: European journal of organic chemistry. Issue 34(2014)
• Page Start: 7605
• Page End: 7613
• Publication Date: 2014-10-21
• Subjects: Intercalations -- Calixarenes -- Heterocycles -- Polycycles -- DNA recognition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403050
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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 IC50 of 95 nM . 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. Abstract : We have synthesized polycyclic‐aromatic‐hydrocarbon‐presenting (PAH‐presenting) calix[4]arene conjugates with pyrenylisoxazolidine moieties linked to the calix[4]arene exo rim as DNA‐intercalating agents. The most potent one showed an IC50 of 95 nM for FTC133 cells; circular dichroism and docking studies suggest that it acts as a monointercalator that penetrates from the minor groove.