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Zn(II) complexes of (E)-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline in combination with non-steroidal anti-inflammatory drug sodium diclofenac: Structure, DNA binding and photo-cleavage studies, antioxidant activity and interaction with albumin.
Journal of Inorganic Biochemistry ( IF 3.9 ) Pub Date : 2020-07-18 , DOI: 10.1016/j.jinorgbio.2020.111194
Chrisoula Kakoulidou 1 , Panagiotis S Gritzapis 2 , Antonios G Hatzidimitriou 1 , Konstantina C Fylaktakidou 3 , George Psomas 1
Affiliation  

The interaction of the novel quinazoline (E)-4-(2-(pyridin-2-ylmethylene)hydrazinyl)quinazoline (L) with Zn2+ was performed in the absence or presence of the non-steroidal anti-inflammatory drug sodium diclofenac (Nadicl) and resulted in the formation of complexes [Zn(L)2](NO3)2·MeOH (1·MeOH) and [Zn(L)(dicl-O)2]·MeOH (2·MeOH), respectively. The two complexes were characterized by IR and 1H NMR spectroscopy and by single-crystal X-ray crystallography. In these complexes, L was tridentately coordinated to Zn(II) via the quinazoline, hydrazone and pyridine nitrogen atoms. Further studies concerning the behavior of the compounds towards calf-thymus (CT) DNA and supercoiled circular pBluescript KS II plasmid DNA (pDNA) have been performed. The complexes may bind to CT DNA via intercalation, with complex 1 showing higher binding affinity than 2. The complexes may cleave pDNA in the absence or presence of irradiation with UVA, UVB or visible light and the most active pDNA-cleavager is compound 1. The binding constants of the compounds for bovine serum albumin were calculated and the subdomain of the albumin where the compounds prefer to bind was determined. The free radical scavenging ability of the compounds was evaluated towards 1,1-diphenyl-picrylhydrazyl and 2,2΄-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radicals with complex 2 being the most active compound. Thus, complex of type 1 maybe a lead compound for the development of novel DNA-binders and DNA-cleavers or photo-cleavers for medical and biotechnological “on demand” applications, whereas the structure of complex type 2 may provide novel antioxidants and radical scavengers.



中文翻译:

(E)-4-(2-(吡啶-2-基亚甲基)肼基)喹唑啉与非甾体抗炎药双氯芬酸钠的Zn(II)配合物:结构,DNA结合和光裂解研究,抗氧化活性和与白蛋白的相互作用。

在不存在或存在非甾体类抗炎药双氯芬酸钠的情况下,进行了新型喹唑啉(E)-4-(2-(吡啶-2-基亚甲基)肼基)喹唑啉(L)与Zn 2+的相互作用。(Nadicl)并形成络合物[Zn(L2 ](NO 32 ·MeOH(1 ·MeOH)和[Zn(L)(dicl-O)2 ]·MeOH(2 ·MeOH),分别。两种配合物通过IR和1 H NMR光谱以及单晶X射线晶体学表征。在这些复合物中,L通过喹唑啉,和吡啶氮原子三齿配位于Zn(II)。已经进行了有关化合物对小胸腺(CT)DNA和超螺旋环状pBluescript KS II质粒DNA(pDNA)行为的进一步研究。配合物可以通过嵌入与CT DNA结合,配合物1的结合亲和力比2高。复合物可在不存在或存在UVA,UVB或可见光照射的情况下切割pDNA,最活跃的pDNA裂解剂是化合物1。计算化合物对牛血清白蛋白的结合常数,并确定化合物较喜欢结合的白蛋白亚结构域。评价了化合物对1,1-二苯基-吡啶基肼基和2,2′-叠氮基双-(3-乙基苯并噻唑啉-6-磺酸)自由基的清除能力,其中配合物2是活性最高的化合物。因此,类型1的复合物可能是开发用于医学和生物技术“按需”应用的新型DNA粘合剂和DNA切割器或光切割器的先导化合物,而类型2的复合物的结构可能提供新型的抗氧化剂和自由基清除剂。

更新日期:2020-07-28
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