Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues.
Overproduction of reactive oxygen species results in oxidative stress that can cause fatal damage to vital cell structures. It is known that the use of antioxidants could be beneficial in the prevention or delay of numerous diseases associated with oxidative stress. Melatonin (MLT) is known as a powerful free-radical scavenger and antioxidant. It was found that indole ring of MLT can be employed by bioisosteric replacement by other aromatic rings. Quinoline derivatives constitute an important class of compounds for new drug development. Owing to quinoline and hydrazones appealing physiological properties and are mostly found in numerous biologically active compounds a series of quinoline-2-carbaldehyde hydrazone derivatives were synthesized as bioisosteric analogues of MLT, characterized and in vitro antioxidant activity was investigated by evaluating their reducing effect against oxidation of a redox-sensitive fluorescent probe. Cytotoxicity potential of all compounds was investigated both by lactate dehydrogenase leakage assay and by MTT assay.
a Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Erciyes University , Melikgazi , Kayseri , Turkey .
M Orhan
MO
Puskullu
b Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Erzincan University , Yalnizbag Yerleskesi , Erzincan , Turkey .
Hanif
H
Shirinzadeh
c Department of Pharmaceutical Toxicology, Faculty of Pharmacy , Ege University , Izmir , Turkey , and.
Merve
M
Nenni
c Department of Pharmaceutical Toxicology, Faculty of Pharmacy , Ege University , Izmir , Turkey , and.
Hande
H
Gurer-Orhan
d Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Ankara University , Tandogan , Ankara , Turkey.
Sibel
S
Suzen
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016466:CHO Cells; D002470:Cell Survival / Q000187:drug effects; D003412:Cricetulus; D004305:Dose-Response Relationship, Drug; D005456:Fluorescent Dyes / Q000737:chemistry / Q000378:metabolism; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008550:Melatonin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D018384:Oxidative Stress / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000037:antagonists & inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship
D000975:Antioxidants; D005456:Fluorescent Dyes; D006835:Hydrazones; D011804:Quinolines; D017382:Reactive Oxygen Species; C000611337:quinoline-2-carbaldehyde hydrazone; D008550:Melatonin
Antioxidant; MTT; hydrazone; lactate dehydrogenase leakage; melatonin; quinoline