Activation and inhibition effects of some natural products on human cytosolic CAI and CAII

被引:17
作者
Adem, Sevki [1 ]
Akkemik, Ebru [2 ]
Aksit, Huseyin [3 ]
Guller, Pinar [4 ]
Tufekci, Ali Riza [1 ]
Demirtas, Ibrahim [1 ]
Ciftci, Mehmet [5 ]
机构
[1] Cankiri Karatekin Univ, Dept Chem, Fac Sci, TR-18100 Cankiri, Turkey
[2] Siirt Univ, Dept Engn & Architecture Food Engn, TR-56100 Siirt, Turkey
[3] Erzincan Univ, Fac Pharm, TR-24100 Erzincan, Turkey
[4] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey
[5] Bingol Univ, Dept Sci & Arts, Bingol, Turkey
关键词
Carbonic anhydrase; Natural product; Inhibition; Activation; Docking; CARBONIC-ANHYDRASE INHIBITORS; PHENOLIC-COMPOUNDS; FLAVONOIDS;
D O I
10.1007/s00044-019-02329-1
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Carbonic anhydrases (CAs) play a significant function in diverse pathological and physiological processes. Their inhibitors and activators are suitable molecules to use as a drug in the treatment of different disease. In the present study, seven natural compounds, namely didymin, retusin isoquercitrin, silymarin, verbascoside, teucroside, and 3'-O-methylhypolaetin 7-O-[6"'-O-acetyl-beta-D-allopyranosyl-(1 -> 2)]-6 ''-O-acetyl-beta-D-glucopyranoside were isolated from Mentha spicata, Sideritis libanotica linearis, Platanus orientalis, Teucrium chamaedrys subsp. chamaedrys, and Silybum marianum. The influences of compounds on the carbonic anhydrase I(hCAI) and II(hCAII) purified from human erythrocytes were tested. Five phenolic compounds acted as an inhibitor on the activity of hCAI, and IC50 values were computed between 18.16 and 172.5 mu M. Isozyme hCAII is only inhibited by silymarin with an IC50 value of 43.12 mu M. This isoenzyme was effectively activated by five natural compounds with AC(50) values in the range of 2.98-18.53 mu M. To understand the binding patterns of molecules that show activation effect against hCAII, molecular docking was done using Leadit 2.3.2 software, and calculated between -19.05 and -14.42 (kJ/mol) binding energies. Both in vitro and in silico results demonstrated that the best activators against hCAII were teucroside and isoquercitrin, with AC(50) values of 2.98 and 3.17 mu M, and binding energies -19.05 and -18.01 (kJ/mol), respectively. According to the ADME results, retusin demonstrated physicochemical and pharmacokinetic properties specific to the drug candidates.
引用
收藏
页码:711 / 722
页数:12
相关论文
共 40 条
  • [1] Inhibitory and Activating Effects of Some Flavonoid Derivatives on Human Pyruvate Kinase Isoenzyme M2
    Adem, Sevki
    Aslan, Abdulselam
    Ahmed, Ishtiaq
    Krohn, Karsten
    Guler, Caglar
    Comakli, Veysel
    Demirdag, Ramazan
    Kuzu, Muslum
    [J]. ARCHIV DER PHARMAZIE, 2016, 349 (02) : 132 - 136
  • [2] Accumulation of silymarin in milk thistle seeds under drought stress
    Afshar, Reza Keshavarz
    Chaichi, Mohammad Reza
    Jovini, Mahya Ansari
    Jahanzad, Emad
    Hashemi, Masoud
    [J]. PLANTA, 2015, 242 (03) : 539 - 543
  • [3] Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms?
    Alterio, Vincenzo
    Di Fiore, Anna
    D'Ambrosio, Katia
    Supuran, Claudiu T.
    De Simone, Giuseppina
    [J]. CHEMICAL REVIEWS, 2012, 112 (08) : 4421 - 4468
  • [4] Synthesis, characterization, antimicrobial activity and carbonic anhydrase enzyme inhibitor effects of salicilaldehyde-N-methyl p-toluenesulfonylhydrazone and its Palladium(II), Cobalt(II) complexes
    Alyar, Saliha
    Adem, Sevki
    [J]. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 131 : 294 - 302
  • [5] Investigation of the Effects of Some Drugs and Phenolic Compounds on Human Dihydrofolate Reductase Activity
    Aslan, Erdem
    Adem, Sevki
    [J]. JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2015, 29 (03) : 135 - 139
  • [6] Carbonic anhydrase activators. The first activation study of a coral secretory isoform with amino acids and amines
    Bertucci, Anthony
    Zoccola, Didier
    Tambutte, Sylvie
    Vullo, Daniela
    Supuran, Claudiu T.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (06) : 2300 - 2303
  • [7] Crystal Structure of Carbonic Anhydrase II in Complex with an Activating Ligand: Implications in Neuronal Function
    Bhatt, Avni
    Mondal, Utpal K.
    Supuran, Claudiu T.
    Ilies, Marc A.
    McKenna, Robert
    [J]. MOLECULAR NEUROBIOLOGY, 2018, 55 (09) : 7431 - 7437
  • [8] BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
  • [9] Flavonoids: Prospective Drug Candidates
    Cazarolli, Luisa Helena
    Zanatta, Leila
    Alberton, Elga Heloisa
    Reis Bonorino Figueiredo, Maria Santos
    Folador, Poliane
    Damazio, Rosangela Guollo
    Pizzolatti, Moacir Geraldo
    Mena Barreto Silva, Fatima Regina
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2008, 8 (13) : 1429 - 1440
  • [10] Chemopreventive Agents and Inhibitors of Cancer Hallmarks: May Citrus Offer New Perspectives?
    Cirmi, Santa
    Ferlazzo, Nadia
    Lombardo, Giovanni E.
    Maugeri, Alessandro
    Calapai, Gioacchino
    Gangemi, Sebastiano
    Navarra, Michele
    [J]. NUTRIENTS, 2016, 8 (11):