Investigation of Antioxidant, Anticholinesterase Inhibitory, Tyrosinase Inhibitory and Urease Inhibitory Activities of Some Hydrazone Derivatives

Abstract

In this study was aimed to investigate antioxidant, anticholinesterase inhibitory, tyrosinase inhibitory and urease inhibitory activities of the synthesized fifteen hydrazone compounds (1-15). According to the antioxidant activity assay results, compound 8 (IC50= 22.40±0.87 μM) and 6 (IC50= 29.48±0.71 μM) showed the best lipid peroxidation inhibitory activity. The compound 6 and 8 exhibited better activity IC50 value of 21.34±0.11 and 25.33±0.27 μM, respectively, than standard BHT (IC50= 54.97±0.99 μM) in DPPH free scavenging activity. Among the tested compound, compound 6 (IC50= 11.71±0.28 μM) and 8 (IC50= 16.45±0.31 μM) showed the best cation radical scavenging activity. Compound 6, 11, 10, 8, 1, 7, and 14 indicated the best CUPRAC capacity activity with an A0.5 value of 15.12±0.00, 17.91±0.01, 21.18±0.00, 23.25±0.03, 24.29±0.01, 26.83±0.01, and 32.35±0.02 μM, respectively, than the standard antioxidants, α-tocopherol (A0.5=40.55±0.04 μM) and BHA (A0.5=32.71±0.02 μM) using as standards. Compound 14 (IC50=11.38±0.44 μM) and 6 (IC50=18.77±0.61 μM) showed the highest acetylcholinesterase inhibitory activity. Among them, compound 2, 14, 6, 3, 13, 8, 10, 11, and 12 were determined to have butyrylcholinesterase inhibitory activity IC50 value of 24.12±0.65, 27.46±0.44, 29.33±0.21, 30.26±0.05, 35.60±0.53, 37.42±0.48, 39.44±0.74, 42.75±0.22, and 45.40±0.76 μM, respectively, than the standard galantamine (IC50=44.03±0.14 μM). According to the tyrosinase assay results, compound 3 (IC50=12.20±0.44 mM), 4 (IC50=14.76±0.90 mM), 15 (IC50=16.28±0.41 mM), 5 (IC50=18.39±0.87 mM), and 2 (IC50=20.12±0.33 mM) exhibited the best tyrosinase inhibitory activity. Compound 6 (IC50=19.20±0.48 mM) and 14 (IC50=22.62±0.38 μM) founded that the urease inhibitory activity are significant when compared with the thiourea (IC50=23.08±0.19 μM).

Keywords

• Hydrazone
• antioxidant activity
• tyrosinase inhibitory activity
• urease inhibitory activity
• anticholinesterase inhibitory activity

Bazı Hidrazon Türevlerinin Antioksidan, Antikolinesteraz İnhibisyon, Tirozinaz İnhibisyon ve Üreaz İnnhibisyon Aktivitelerinin Araştırılması

Öz

Bu çalışmada, 15 hidrazon molekülünün (1-15) antioksidan, antikolinesteraz inhibisyon, tirozinaz inhibisyon ve üreaz inhibisyon aktivitelerinin araştırılması amaçlandı. Antioksidan aktivite test sonuçlarına göre, 8 (IC50=22.40±0.87 μM) ve 6 (IC50=29.48±0.71 μM) numaralı moleküller en iyi lipit peroksidaz inhibisyon aktivitesine sahip olduğunu gösterdi. 6 ve 8 numaralı moleküllerin DPPH serbest radikal giderim aktivitesi, standart BHT’ya (IC50=54.97±0.99 μM) göre sırasıyla 21.34±0.11 ve 25.33±0.27 μM’lik IC50 değerleri ile test edilen moleküllere istinaden daha iyi aktivite sergilediği saptandı. Test edilen moleküller arasında 6 (IC50=11.71±0.28 μM) ve 8 (IC50=16.45±0.31 μM) numaralı moleküllerin en iyi katyon radikal giderim aktivitesine sahip olduğunu bulundu. 6, 11, 10, 8, 1, 7 ve 14 numaralı moleküller α-tokoferol (A0.5=40.55±0.04 μM) ve BHA (A0.5=32.71±0.02 μM) antioksidan standartlarına göre 15.12±0.00, 17.91±0.01, 21.18±0.00, 23.25±0.03, 24.29±0.01, 26.83±0.01 ve 32.35±0.02 μM’lik A0.5 değerleriyle en iyi CUPRAC kapasite aktivitesine sahip olduğu saptandı. 14 (IC50=11.38±0.44 μM) ve 6 (IC50=18.77±0.61 μM) numaralı moleküller en iyi asetilkolinesteraz inhibisyon aktivitesi sergilerken, 2, 14, 6, 3, 13, 8, 10, 11 ve 12 numaralı moleküllerin ise BChE standardı olarak kullanılan galantamine (IC50=44.03±0.14 μM) göre sırasıyla 24.12±0.65, 27.46±0.44, 29.33±0.21, 30.26±0.05, 35.60±0.53, 37.42±0.48, 39.44±0.74, 42.75±0.22, and 45.40±0.76 μM’lik IC50 değerleriyle en iyi butirilkolinesteraz inhibisyon aktivitesine sahip oldukları belirlendi. Tiroazinaz test sonuçlarına göre, 3 (IC50=12.20±0.44 mM), 4 (IC50=14.76±0.90 mM), 15 (IC50=16.28±0.41 mM), 5 (IC50=18.39±0.87 mM), ve 2 (IC50=20.12±0.33 mM) numaralı moleküllerin en iyi tirozinaz inhibisyon aktivitesi sergilendiği bulundu. Test edilen hidrazon moleküllerinin üreaz inhibisyon aktivitesi standart olarak kullanılan tiyoüre (IC50=23.08±0.19 μM) ile mukayese edilediğinde 6 (IC50=19.20±0.48 mM) ve 4 (IC50=22.62±0.38 μM) numaralı hidrazon moleküllerinin daha iyi olduğu tespit edildi.

Anahtar Kelimeler

• Hidrazon
• antioksidan aktivite
• antikolinesteraz inhibisyon aktivite
• tirozinaz inhibisyon aktivite
• üreaz inhibisyon aktivite

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