Next Article in Journal / Special Issue
Advances in Drug Discovery of New Antitubercular Multidrug-Resistant Compounds
Previous Article in Journal
Syntheses of Radioiodinated Pyrimidine-2,4,6-Triones as Potential Agents for Non-Invasive Imaging of Matrix Metalloproteinases
Previous Article in Special Issue
Synthesis and Pharmacological Properties of Novel Esters Based on Monoterpenoids and Glycine
Open AccessArticle

Chiral Derivatives of Xanthones: Investigation of the Effect of Enantioselectivity on Inhibition of Cyclooxygenases (COX-1 and COX-2) and Binding Interaction with Human Serum Albumin

1
Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira nº 228, 4050-313 Porto, Portugal
2
Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal
3
CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde, Rua Central de Gandra 1317, 4585-116 Gandra PRD, Portugal
4
REQUIMTE, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050‑313 Porto, Portugal
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Pharmaceuticals 2017, 10(2), 50; https://doi.org/10.3390/ph10020050
Received: 22 April 2017 / Revised: 25 May 2017 / Accepted: 27 May 2017 / Published: 31 May 2017
Searching of new enantiomerically pure chiral derivatives of xanthones (CDXs) with potential pharmacological properties, particularly those with anti-inflammatory activity, has remained an area of interest of our group. Herein, we describe in silico studies and in vitro inhibitory assays of cyclooxygenases (COX-1 and COX-2) for different enantiomeric pairs of CDXs. The evaluation of the inhibitory activities was performed by using the COX Inhibitor Screening Assay Kit. Docking simulations between the small molecules (CDXs; known ligands and decoys) and the enzyme targets were undertaken with AutoDock Vina embedded in PyRx—Virtual Screening Tool software. All the CDXs evaluated exhibited COX-1 and COX-2 inhibition potential as predicted. Considering that the (S)-(−)-enantiomer of the nonsteroidal anti-inflammatory drug ketoprofen preferentially binds to albumin, resulting in lower free plasma concentration than (R)-(+)-enantiomer, protein binding affinity for CDXs was also evaluated by spectrofluorimetry as well as in in silico. For some CDXs enantioselectivity was observed. View Full-Text
Keywords: chiral derivatives of xanthones; cyclooxygenase; albumin; enantioselectivity; docking chiral derivatives of xanthones; cyclooxygenase; albumin; enantioselectivity; docking
Show Figures

Figure 1

MDPI and ACS Style

Fernandes, C.; Palmeira, A.; Ramos, I.I.; Carneiro, C.; Afonso, C.; Tiritan, M.E.; Cidade, H.; Pinto, P.C.A.G.; Saraiva, M.L.M.F.S.; Reis, S.; Pinto, M.M.M. Chiral Derivatives of Xanthones: Investigation of the Effect of Enantioselectivity on Inhibition of Cyclooxygenases (COX-1 and COX-2) and Binding Interaction with Human Serum Albumin. Pharmaceuticals 2017, 10, 50. https://doi.org/10.3390/ph10020050

AMA Style

Fernandes C, Palmeira A, Ramos II, Carneiro C, Afonso C, Tiritan ME, Cidade H, Pinto PCAG, Saraiva MLMFS, Reis S, Pinto MMM. Chiral Derivatives of Xanthones: Investigation of the Effect of Enantioselectivity on Inhibition of Cyclooxygenases (COX-1 and COX-2) and Binding Interaction with Human Serum Albumin. Pharmaceuticals. 2017; 10(2):50. https://doi.org/10.3390/ph10020050

Chicago/Turabian Style

Fernandes, Carla; Palmeira, Andreia; Ramos, Inês I.; Carneiro, Carlos; Afonso, Carlos; Tiritan, Maria E.; Cidade, Honorina; Pinto, Paula C.A.G.; Saraiva, M. L.M.F.S.; Reis, Salette; Pinto, Madalena M.M. 2017. "Chiral Derivatives of Xanthones: Investigation of the Effect of Enantioselectivity on Inhibition of Cyclooxygenases (COX-1 and COX-2) and Binding Interaction with Human Serum Albumin" Pharmaceuticals 10, no. 2: 50. https://doi.org/10.3390/ph10020050

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop