Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery

被引:134
作者
Nocentini, Alessio [1 ]
Supuran, Claudiu T. [1 ]
机构
[1] Univ Florence, Sect Pharmaceut & Nutraceut Sci, Dept Neurosci Psychol Drug Res & Childs Hlth NEUR, Florence, Italy
关键词
Carbonic anhydrase; inhibitor; activator; sulfonamide; coumarin; SLC-0111; inhibition mechanism; X-ray crystallography; AFFINITY ISOZYMES I; ZINC-BINDING GROUP; RAY CRYSTALLOGRAPHIC STRUCTURE; ISOFORM-SELECTIVE INHIBITORS; CRYSTAL-STRUCTURE; ACTIVE-SITE; CA-I; AROMATIC/HETEROCYCLIC SULFONAMIDES; EXTRACELLULAR DOMAIN; WATER-MOLECULES;
D O I
10.1080/17460441.2019.1651289
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Introduction: Of the 15 human carbonic anhydrase (CA, EC 4.2.1.1) isoforms known to date, for 11 the crystal structure is known. Many different classes of CA inhibitors (CAIs) were reported in the last decade, with a wealth of inhibition mechanisms, where apart from the classical one, the inhibitors do not bind to the zinc ion from the active site. The zinc binders (sulfonamides, dithiocarbamates and their isosteres, thiols, selenols, carboxylates, hydroxamates, carbamates) are not isoform-selective inhibitors, but the specificity of action may be achieved by decorating their scaffolds with tails that interact with amino acids at the entrance of the active site. Areas covered: Herein, the authors review the advances in the structural annotation of human CAs. Furthermore, the authors look at the impact on drug discovery efforts as well as providing their expert perspectives. Expert opinion: CAs are a unique example among metalloenzymes for which all regions of their spacious active sites may be used for inhibitor/activator binding, leading to a variety of inhibition mechanisms and profiles for the many chemotypes modulating their activity. This is exploited for the drug design of increasingly efficient and isoform-selective inhibitors, useful for many pharmacological applications.
引用
收藏
页码:1175 / 1197
页数:23
相关论文
共 177 条
[1]   Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride [J].
Abbate, F ;
Coetzee, A ;
Casini, A ;
Ciattini, S ;
Scozzafava, A ;
Supuran, CT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :337-341
[2]   Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide [J].
Abbate, F ;
Casini, A ;
Scozzafava, A ;
Supuran, CT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2357-2361
[3]   Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: a patent review [J].
Aggarwal, Mayank ;
Kondeti, Bhargav ;
McKenna, Robert .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (06) :717-724
[4]   Structural annotation of human carbonic anhydrases [J].
Aggarwal, Mayank ;
Boone, Christopher D. ;
Kondeti, Bhargav ;
McKenna, Robert .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (02) :267-277
[5]   Discovery of Novel Nonsteroidal Anti-Inflammatory Drugs and Carbonic Anhydrase Inhibitors Hybrids (NSAIDs-CAIs) for the Management of Rheumatoid Arthritis [J].
Akgul, Ozlem ;
Mannelli, Lorenzo Di Cesare ;
Vullo, Daniela ;
Angeli, Andrea ;
Ghelardini, Carla ;
Bartolucci, Gianluca ;
Altamimi, Abdulmalik Saleh Alfawaz ;
Scozzafava, Andrea ;
Supuran, Claudiu T. ;
Carta, Fabrizio .
JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (11) :4961-4977
[6]   Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2,4,6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor [J].
Alterio, Vincenzo ;
Esposito, Davide ;
Monti, Simona Maria ;
Supuran, Claudiu T. ;
De Simone, Giuseppina .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2017, 33 (01) :151-157
[7]   Benzoxaborole as a new chemotype for carbonic anhydrase inhibition [J].
Alterio, Vincenzo ;
Cadoni, Roberta ;
Esposito, Davide ;
Vullo, Daniela ;
Di Fiore, Anna ;
Monti, Simona Maria ;
Caporale, Andrea ;
Ruvo, Menotti ;
Sechi, Mario ;
Dumy, Pascal ;
Supuran, Claudiu T. ;
De Simone, Giuseppina ;
Winum, Jean-Yves .
CHEMICAL COMMUNICATIONS, 2016, 52 (80) :11983-11986
[8]   The Structural Comparison Between Membrane-Associated Human Carbonic Anhydrases Provides Insights into Drug Design of Selective Inhibitors [J].
Alterio, Vincenzo ;
Pan, Peiwen ;
Parkkila, Seppo ;
Buonanno, Martina ;
Supuran, Claudiu T. ;
Monti, Simona M. ;
De Simone, Giuseppina .
BIOPOLYMERS, 2014, 101 (07) :769-778
[9]   Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms? [J].
Alterio, Vincenzo ;
Di Fiore, Anna ;
D'Ambrosio, Katia ;
Supuran, Claudiu T. ;
De Simone, Giuseppina .
CHEMICAL REVIEWS, 2012, 112 (08) :4421-4468
[10]   Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX [J].
Alterio, Vincenzo ;
Hilvo, Mika ;
Di Fiore, Anna ;
Supuran, Claudiu T. ;
Pan, Peiwen ;
Parkkila, Seppo ;
Scaloni, Andrea ;
Pastorek, Jaromir ;
Pastorekova, Silvia ;
Pedone, Carlo ;
Scozzafava, Andrea ;
Monti, Simona Maria ;
De Simone, Giuseppina .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (38) :16233-16238