TY - JOUR
T1 - Synthesis of new porphyrin/4-quinolone conjugates and evaluation of their efficiency in the photoinactivation of Staphylococcus aureus
AU - Batalha, Pedro N.
AU - Gomes, Ana T.P.C.
AU - Forezi, Luana S.M.
AU - Costa, Liliana
AU - De Souza, Maria Cecília B.V.
AU - Boechat, Fernanda Da C.S.
AU - Ferreira, Vitor F.
AU - Almeida, Adelaide
AU - Faustino, Maria A.F.
AU - Neves, Maria G.P.M.S.
AU - Cavaleiro, José A.S.
N1 - Publisher Copyright:
© The Royal Society of Chemistry 2015.
PY - 2015/8/14
Y1 - 2015/8/14
N2 - Simple methodologies giving access to a new series of pophyrin/4-quinolone conjugates 6 and to the corresponding intra-cyclized derivatives 8 are described. The key steps to obtain 6 involved palladium-catalyzed amination reactions of 6-bromo-4-quinolones containing N-ethyl, N-pentyl and N-ribofuransyl substituents with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(ii) followed by demetallation. Compounds 8 were obtained from compounds 4, the nickel(ii) complexes of 6, by an oxidative intracylization approach. The new conjugates were fully characterized and the evaluation of singlet oxygen production showed that these compounds possess good to high capability to generate singlet oxygen. The efficacy of these derivatives to photoinactivate Staphylococcus aureus, a Gram-positive bacteria, was evaluated and the best results were obtained with the N-ethyl derivatives 8a and 6a.
AB - Simple methodologies giving access to a new series of pophyrin/4-quinolone conjugates 6 and to the corresponding intra-cyclized derivatives 8 are described. The key steps to obtain 6 involved palladium-catalyzed amination reactions of 6-bromo-4-quinolones containing N-ethyl, N-pentyl and N-ribofuransyl substituents with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(ii) followed by demetallation. Compounds 8 were obtained from compounds 4, the nickel(ii) complexes of 6, by an oxidative intracylization approach. The new conjugates were fully characterized and the evaluation of singlet oxygen production showed that these compounds possess good to high capability to generate singlet oxygen. The efficacy of these derivatives to photoinactivate Staphylococcus aureus, a Gram-positive bacteria, was evaluated and the best results were obtained with the N-ethyl derivatives 8a and 6a.
UR - http://www.scopus.com/inward/record.url?scp=84940470708&partnerID=8YFLogxK
U2 - 10.1039/c5ra11070j
DO - 10.1039/c5ra11070j
M3 - Article
AN - SCOPUS:84940470708
SN - 2046-2069
VL - 5
SP - 71228
EP - 71239
JO - RSC Advances
JF - RSC Advances
IS - 87
ER -