Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions

被引：118
作者：
Ozbey, Fadime [1 ]
Taslimi, Parham [1 ]
Gulcin, Ilhami [1 ,2 ]
Maras, Ahmet [1 ]
Goksu, Sueleyman [1 ]
Supuran, Claudiu T. [3 ,4 ]
机构：
[1] Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey
[2] King Saud Univ, Dept Zool, Coll Sci, Riyadh, Saudi Arabia
[3] Univ Firenze, Dipartimento Chim Ugo Schiff, Florence, Italy
[4] Univ Firenze, Sect Pharmaceut & Nutriceut Sci, Neurofarba Dept, Florence, Italy
来源：
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2016年 / 31卷
关键词：
Acetylcholinesterase; butyrylcholinesterase; carbonic anhydrase; diaryl ethers; enzyme inhibition; TROUT ONCORHYNCHUS-MYKISS; ERYTHROCYTES IN-VITRO; ISOENZYMES HCA I; BIOLOGICAL EVALUATION; BROMOPHENOL DERIVATIVES; SULFONAMIDE DERIVATIVES; ENZYME-ACTIVITY; ISOZYMES I; VIVO; ANTIOXIDANT;
D O I：
10.1080/14756366.2016.1189422
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：
A series of diaryl ethers were synthesized and their human (h) carbonic anhydrase (CA) isoenzymes hCA I and II, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) inhibitory actions were investigated. The new compounds were synthesized from the corresponding phenols and bromobenzenes via the Ullmann reaction, by using dipicolinic acid as a copper (I) complexing ligand. hCA I and II were inhibited with K(i)s in the low nanomolar range of 102.01-127.13nM against hCA I, and of 73.71-113.40nM against hCA II, whereas the inhibition constants against AChE were of 15.35-18.34nM and against BChE in the range of 9.07-22.90nM. The CA inhibition mechanism with these ethers is unknown, but may be similar to that of aryl methyl ethers investigated earlier by computational approaches.
引用
收藏
页码：79 / 85
页数：7
相关论文
共 82 条
[21]   Synthesis and Carbonic Anhydrase Isoenzymes Inhibitory Effects of Brominated Diphenylmethanone and Its Derivatives [J].
Cetinkaya, Yasin ;
Gocer, Hulya ;
Gulcin, Ilhami ;
Menzek, Abdullah .
ARCHIV DER PHARMAZIE, 2014, 347 (05) :354-359
[22]   Synthesis and carbonic anhydrase isoenzymes I and II inhibitory effects of novel benzylamine derivatives [J].
Cetinkaya, Yasin ;
Gocer, Hulya ;
Goksu, Suleyman ;
Gulcin, Ilhami .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2014, 29 (02) :168-174
[23]   Inhibitory effect of obovatol on nitric oxide production and activation of NF-κB/MAP kinases in lipopolysaccharide-treated RAW 264.7 cells [J].
Choi, Myoung Suk ;
Lee, Seung Ho ;
Cho, Ho Seong ;
Kim, Youngsoo ;
Yun, Yeo Pyo ;
Jung, Hai Young ;
Jung, Jae Kyoung ;
Lee, Bum Chun ;
Pyo, Hyeong Bae ;
Hong, Jin Tae .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2007, 556 (1-3) :181-189
[24]  
Çoban TA, 2008, J ENZYM INHIB MED CH, V23, P266, DOI [10.1080/14756360701474780 , 10.1080/14756360701474780]
[25]   Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo [J].
Coban, Taha Abdulkadir ;
Beydemir, Suekrue ;
Guelcin, Ilhami ;
Ekinci, Deniz .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2007, 30 (12) :2257-2261
[26]   Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site [J].
Durdagi, Serdar ;
Senturk, Murat ;
Ekinci, Deniz ;
Balaydin, Halis Turker ;
Goksu, Suleyman ;
Kufrevioglu, O. Irfan ;
Innocenti, Alessio ;
Scozzafava, Andrea ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (04) :1381-1389
[27]   A NEW AND RAPID COLORIMETRIC DETERMINATION OF ACETYLCHOLINESTERASE ACTIVITY [J].
ELLMAN, GL ;
COURTNEY, KD ;
ANDRES, V ;
FEATHERSTONE, RM .
BIOCHEMICAL PHARMACOLOGY, 1961, 7 (02) :88-&
[28]   Thioxocoumarins Show an Alternative Carbonic Anhydrase Inhibition Mechanism Compared to Coumarins [J].
Ferraroni, Marta ;
Carta, Fabrizio ;
Scozzafava, Andrea ;
Supuran, Claudiu T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (01) :462-473
[29]   Design, synthesis, and biological evaluation of a series of alkoxy-3-indolylacetic acids as peroxisome proliferator-activated receptor γ/δ agonists [J].
Gim, Hyo Jin ;
Li, Hua ;
Jeong, Ji Hye ;
Lee, Su Jeong ;
Sung, Mi-Kyung ;
Song, Mi-Young ;
Park, Byung-Hyun ;
Oh, Soo Jin ;
Ryu, Jae-Ha ;
Jeon, Raok .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) :3322-3336
[30]   Spirobisnaphthalenes effectively inhibit carbonic anhydrase [J].
Gocer, Hulya ;
Aslan, Abdulselam ;
Gulcin, Ilhami ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 (03) :503-507
123456789