title: 9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII.
abstract: N-substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4-Dibromo-dibenzo[e,h]bicyclo-[2,2,2]octane-2,3-dicarboximide derivatives (4a-f) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N-substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with Ki values in the range of 117.73-232.87 nM against hCA I and of 69.74-111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII.
authors.affiliation: Kaynasli Vocational College, Düzce University, Düzce, Turkey.|Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
authors.forename: Haydar
authors.initials: H
authors.lastname: Göksu
authors.affiliation: Department of Medical Services and Techniques, Vocational School of Health Services, Gumushane University, Gumushane, Turkey.
authors.forename: Meryem
authors.initials: M
authors.lastname: Topal
authors.affiliation: Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
authors.forename: Ali
authors.initials: A
authors.lastname: Keskin
authors.affiliation: Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
authors.forename: Mehmet S
authors.initials: MS
authors.lastname: Gültekin
authors.affiliation: Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.
authors.forename: Murat
authors.initials: M
authors.lastname: Çelik
authors.affiliation: Faculty of Science, Department of Chemistry, Atatürk University, Erzurum, Turkey.|Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.
authors.forename: İlhami
authors.initials: İ
authors.lastname: Gülçin
authors.affiliation: Dipartimento NEUROFARBA, Università degli Studi di Firenze, Sezione di Scienze Farmaceutiche, Sesto Fiorentino (Firenze), Italy.
authors.forename: Muhammet
authors.initials: M
authors.lastname: Tanc
authors.affiliation: Dipartimento NEUROFARBA, Università degli Studi di Firenze, Sezione di Scienze Farmaceutiche, Sesto Fiorentino (Firenze), Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
chemical_list: D000873:Anthracenes; D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D002256:Carbonic Anhydrases
keywords: Carbonic anhydrase; Enzyme inhibition; Enzyme purification; Isoenzyme