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

被引:137
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
[31]   Xanthates and Trithiocarbonates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Effects in Vivo [J].
Carta, Fabrizio ;
Akdemir, Atilla ;
Scozzafava, Andrea ;
Masini, Emanuela ;
Supuran, Claudiu T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (11) :4691-4700
[32]   Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005-2013) [J].
Carta, Fabrizio ;
Supuran, Claudiu T. .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (06) :681-691
[33]   Sulfonamides: a patent review (2008-2012) [J].
Carta, Fabrizio ;
Scozzafava, Andrea ;
Supuran, Claudiu T. .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2012, 22 (07) :747-758
[34]   Dithiocarbamates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Action in Vivo [J].
Carta, Fabrizio ;
Aggarwal, Mayank ;
Maresca, Alfonso ;
Scozzafava, Andrea ;
McKenna, Robert ;
Masin, Emanuela ;
Supuran, Claudiu T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (04) :1721-1730
[35]   Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations [J].
Carta, Fabrizio ;
Aggarwal, Mayank ;
Maresca, Alfonso ;
Scozzafava, Andrea ;
McKenna, Robert ;
Supuran, Claudiu T. .
CHEMICAL COMMUNICATIONS, 2012, 48 (13) :1868-1870
[36]   Novel therapies for glaucoma: a patent review 2007-2011 [J].
Carta, Fabrizio ;
Supuran, Claudiu T. ;
Scozzafava, Andrea .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2012, 22 (01) :79-88
[37]   5-and 6-Membered (thio)lactones are prodrug type carbonic anhydrase inhibitors [J].
Carta, Fabrizio ;
Maresca, Alfonso ;
Scozzafava, Andrea ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) :267-270
[38]   Polyamines Inhibit Carbonic Anhydrases by Anchoring to the Zinc-Coordinated Water Molecule [J].
Carta, Fabrizio ;
Temperini, Claudia ;
Innocenti, Alessio ;
Scozzafava, Andrea ;
Kaila, Kai ;
Supuran, Claudiu T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (15) :5511-5522
[39]   Carbonic anhydrase inhibitors:: SAR and x-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with Isozymes I, II and IV [J].
Casini, A ;
Antel, J ;
Abbate, F ;
Scozzafava, A ;
David, S ;
Waldeck, H ;
Schäfer, S ;
Supuran, CT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (05) :841-845
[40]   α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters [J].
Cavdar, Huseyin ;
Ekinci, Deniz ;
Talaz, Oktay ;
Saracoglu, Nurullah ;
Senturk, Murat ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2012, 27 (01) :148-154