| Conţinutul numărului revistei |
| Articolul precedent |
| Articolul urmator |
 |
 209 0 |
 SM ISO690:2012MILANESE, Alberto, GORINCIOI, Elena, RAJABI, Mehdi, VISTOLI, Giulio, SANTANIELLO, Enzo. New synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid and evaluation of the influence of adamantyl group on the DNA binding of a naphthoic retinoid. In: Nucleic Acid Therapeutics, 2011, vol. 21, nr. 5, pp. 151-158. ISSN 2159-3337. DOI: https://doi.org/10.1016/j.bioorg.2011.07.003 |
| EXPORT metadate: Google Scholar Crossref CERIF DataCite Dublin Core |
  Nucleic Acid Therapeutics |
||||||
| Volumul 21, Numărul 5 / 2011 / ISSN 2159-3337 /ISSNe 2159-3345 | ||||||
|
||||||
| DOI:https://doi.org/10.1016/j.bioorg.2011.07.003 | ||||||
| Pag. 151-158 | ||||||
|
||||||
| Vezi articolul | ||||||
| Rezumat | ||||||
6[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene®), a synthetic aromatic retinoid specific for RARβ and RARγ receptors, has been prepared utilizing a Pd/C-mediated Suzuki coupling between 6-bromo-2-naphthoic acid and 4-methoxyphenyl boronic acid, followed by introduction of an adamantyl group in the position 3 of the formed 6-(4-methoxyphenyl)-2-naphthoic acid. The interaction of 6-(4-methoxyphenyl)-2- naphthoic acid/ethyl ester and the 3-adamantyl analogs with DNA was studied in aqueous solution at physiological conditions by UV-vis spectroscopy. The calculated binding constants Kligand-DNA ranged between 1.1 × 104 M-1 and 1.1 × 105 M-1, the higher values corresponding to those of the adamantylated compounds. Molecular modeling studies have emphasized that the intercalative binding of adapalene and its derivatives to DNA is mainly stabilized by hydrophobic interactions related to the presence of the adamantyl group. |
||||||
| Cuvinte-cheie 6[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, DNA intercalative binding, Hydrophobic interactions, Naphthoic retinoids, Suzuki coupling |
||||||
|
|
|
|
