Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases

被引:31
作者
Karali, Nilgun [1 ]
Akdemir, Atilla [2 ]
Goktas, Fusun [1 ]
Elma, Pinar Eraslan [1 ]
Angeli, Andrea [3 ]
Kizilirmak, Merih [1 ]
Supuran, Claudiu T. [3 ]
机构
[1] Istanbul Univ, Dept Pharmaceut Chem, Fac Pharm, TR-34116 Istanbul, Turkey
[2] Bezmialem Vakif Univ, Dept Pharmacol, Comp Aided Drug Discovery Lab, Fac Pharm, TR-34093 Istanbul, Turkey
[3] Univ Firenze, Sez Sci Farmaceut, Dept NEUROFARBA, I-50019 Florence, Italy
关键词
Carbonic anhydrase; Isatin; 2-Indolinone; Docking; IN-VITRO ANTICANCER; ISATIN-BETA-THIOSEMICARBAZONES; MULTIDRUG-RESISTANT CELLS; ANTITUBERCULOSIS ACTIVITY; DERIVATIVES; ANALOGS; AGENTS; CYTOTOXICITY; COMPLEXES; LIGANDS;
D O I
10.1016/j.bmc.2017.05.029
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Human carbonic anhydrases IX and XII are upregulated in many tumors and form a novel target for new generation anticancer drugs. Here we report the synthesis of novel 2-indolinone derivatives with the sulfonamide group as a zinc binding moiety. Enzyme inhibition assays confirmed that the compounds showed selectivity against hCA IX and XII over the widely distributed off-targets hCA I and II. Molecular modelling studies were performed to suggest modes of binding for these compounds. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3714 / 3718
页数:5
相关论文
共 31 条
[1]   Synthesis of Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease-Part II [J].
Abdel-Rahman, Reda M. ;
Makki, Mohammad Saleh I. T. ;
Bawazir, Wafa A. Baker .
E-JOURNAL OF CHEMISTRY, 2010, 7 :S93-S102
[2]   Isatin analogs as novel inhibitors of Candida spp. β-carbonic anhydrase enzymes [J].
Akdemir, Atilla ;
Guzel-Akdemir, Ozlen ;
Karali, Nilgun ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (08) :1648-1652
[3]   Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage. activities [J].
Ali, Amna Qasem ;
Teoh, Siang Guan ;
Salhin, Abdussalam ;
Eltayeb, Naser Eltaher ;
Ahamed, Mohamed B. Khadeer ;
Majid, A. M. S. Abdul .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 125 :440-448
[4]   Anti-infective carbonic anhydrase inhibitors: a patent and literature review [J].
Capasso, Clemente ;
Supuran, Claudiu T. .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (06) :693-704
[5]   Reactions of diorganotin(IV) oxides with isatin 3-and 2-thiosemicarbazones and with isatin 2,3-bis(thiosemicarbazone): influence of diphenyldithiophosphinic acid (isatin=1H-indole-2,3-dione) [J].
Casas, JS ;
Castiñeiras, A ;
Rodríguez-Argüelles, MC ;
Sánchez, A ;
Sordo, J ;
Vázquez-López, A ;
Vázquez-López, EM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (22) :4056-4063
[6]   Carbonic anhydrase inhibitors. Zonisamide is an effective inhibitor of the cytosolic isozyme II and mitochondrial isozyme V: solution and X-ray crystallographic studies [J].
De Simone, G ;
Di Fiore, A ;
Menchise, V ;
Pedone, C ;
Antel, J ;
Casini, A ;
Scozzafava, A ;
Wurl, M ;
Supuran, CT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (09) :2315-2320
[7]   Antiobesity carbonic anhydrase inhibitors [J].
De Simone, Giuseppina ;
Supuran, Claudiu T. .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2007, 7 (09) :879-884
[8]   Synthesis, characterization and antimicrobial activities of mixed ligand transition metal complexes with isatin monohydrazone Schiff base ligands and heterocyclic nitrogen base [J].
Devi, Jai ;
Batra, Nisha .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 135 :710-719
[9]   Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies [J].
Eldehna, Wagdy M. ;
Al-Ansary, Ghada H. ;
Bua, Silvia ;
Nocentini, Alessio ;
Gratteri, Paola ;
Altoukhy, Ayman ;
Ghabbour, Hazem ;
Ahmed, Hanaa Y. ;
Supuran, Claudiu T. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 127 :521-530
[10]   Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII [J].
Eldehna, Wagdy M. ;
Fares, Mohamed ;
Ceruso, Mariangela ;
Ghabbour, Hazem A. ;
Abou-Seri, Sahar M. ;
Abdel-Aziz, Hatem A. ;
Abou El Ella, Dalal A. ;
Supuran, Claudiu T. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 110 :259-266