Rational Design, Synthesis and Evaluation of Coumarin Derivatives as Protein-protein Interaction Inhibitors

被引:6
作者
De Luca, Laura [1 ]
Agharbaoui, Fatima E. [1 ]
Gitto, Rosaria [1 ]
Buemi, Maria Rosa [1 ]
Christ, Frauke [2 ,3 ]
Debyser, Zeger [2 ,3 ]
Ferro, Stefania [1 ]
机构
[1] Univ Messina, Dipartimento Sci Chim Biol Farmaceut & Ambientali, I-98168 Messina, Italy
[2] Katholieke Univ Leuven, Mol Virol & Gene Therapy, Kapucijnenvoer 33, B-3000 Leuven, Flanders, Belgium
[3] IRC KULAK, Kapucijnenvoer 33, B-3000 Leuven, Flanders, Belgium
关键词
HIV-1; IN; LEDGF; p75; Docking; Molecular Dynamics; SMALL-MOLECULE INHIBITORS; LEDGF/P75; BINDING-SITE; HIV-1; INTEGRASE; COFACTOR LEDGF/P75; DRUG DISCOVERY; ANTIRETROVIRAL THERAPY; BIOLOGICAL EVALUATION; FORCE-FIELD; IN-VITRO; REPLICATION;
D O I
10.1002/minf.201501034
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Herein we describe the design and synthesis of a new series of coumarin derivatives searching for novel HIV-1 integrase (IN) allosteric inhibitors. All new obtained compounds were tested in order to evaluate their ability to inhibit the interaction between the HIV-1 IN enzyme and the nuclear protein lens epithelium growth factor LEDGF/p75. A combined approach of docking and molecular dynamic simulations has been applied to clarify the activity of the new compounds. Specifically, the binding free energies by using the method of molecular mechanics-generalized Born surface area (MM-GBSA) was calculated, whereas hydrogen bond occupancies were monitored throughout simulations methods.
引用
收藏
页码:460 / 473
页数:14
相关论文
共 55 条
[1]   Inhibitory profile of a LEDGF/p75 peptide against HIV-1 integrase: Insight into integrase-DNA complex formation and catalysis [J].
Al-Mawsawi, Laith Q. ;
Christ, Frauke ;
Dayam, Raveendra ;
Debyser, Zeger ;
Neamati, Nouri .
FEBS LETTERS, 2008, 582 (10) :1425-1430
[2]   Beyond virological suppression: the role of adherence in the late HAART era [J].
Ammassari, Adriana ;
Trotta, Maria Paola ;
Shalev, Noga ;
Marconi, Patrizia ;
Antinori, Andrea .
ANTIVIRAL THERAPY, 2012, 17 (05) :785-792
[3]  
[Anonymous], 2015, GLOB AIDS RRESPONSE
[4]  
[Anonymous], PYMOL MOL GRAPHICS S
[5]   Cardiovascular and cerebrovascular events in patients treated for human immunodeficiency virus infection [J].
Bozzette, SA ;
Ake, CF ;
Tam, HK ;
Chang, SW ;
Louis, TA .
NEW ENGLAND JOURNAL OF MEDICINE, 2003, 348 (08) :702-710
[6]   Identification of the LEDGF/p75 binding site in HIV-1 integrase [J].
Busschots, Katrien ;
Voet, Arnout ;
De Maeyer, Marc ;
Rain, Jean-Christophe ;
Emiliani, Stephane ;
Benarous, Richard ;
Desender, Linda ;
Debyser, Zeger ;
Christ, Frauke .
JOURNAL OF MOLECULAR BIOLOGY, 2007, 365 (05) :1480-1492
[7]   Structural basis for the recognition between HIV-1 integrase and transcriptional coactivator p75 [J].
Cherepanov, P ;
Ambrosio, ALB ;
Rahman, S ;
Ellenberger, T ;
Engelman, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (48) :17308-17313
[8]   Drug discovery from natural sources [J].
Chin, Young-Won ;
Balunas, Marcy J. ;
Chai, Hee Byung ;
Kinghorn, A. Douglas .
AAPS JOURNAL, 2006, 8 (02) :E239-E253
[9]   The LEDGF/p75 integrase interaction, a novel target for anti-HIV therapy [J].
Christ, Frauke ;
Debyser, Zeger .
VIROLOGY, 2013, 435 (01) :102-109
[10]   Small-Molecule Inhibitors of the LEDGF/p75 Binding Site of Integrase Block HIV Replication and Modulate Integrase Multimerization [J].
Christ, Frauke ;
Shaw, Stephen ;
Demeulemeester, Jonas ;
Desimmie, Belete A. ;
Marchand, Arnaud ;
Butler, Scott ;
Smets, Wim ;
Chaltin, Patrick ;
Westby, Mike ;
Debyser, Zeger ;
Pickford, Chris .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2012, 56 (08) :4365-4374