Metal based biologically active compounds: Design, synthesis, DNA binding and antidiabetic activity of 6-methyl-3-formyl chromone derived hydrazones and their metal (II) complexes

Philip, Jessica Elizabeth; Shahid, Muhammad; Kurup, M.R. Prathapachandra; Velayudhan, Mohanan Puzhavoorparambil

doi:10.1016/j.jphotobiol.2017.09.003

Cited by 57 publications

(20 citation statements)

References 52 publications

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“…For example, 2-[2-bromoethyliminomethyl]-4-[ethoxymethyl]phenol derivative Zn-derivative manifests a higher binding constant than copper and nickel derivatives ( Lee et al, 2016 ). Similarly, 6-methyl-3-formyl chromone-derived hydrazine complexes with Ni have a higher binding constant to DNA than Zn and Cu complexes ( Philip et al, 2017 ). Zn and Co phthalocyanine complexes bind to DNA in different ways; the former is an intercalator and the latter a groove binder ( Özen, Günel & Baran, 2018 ).…”

Section: Discussionmentioning

confidence: 99%

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Ļeonova

Shvirksts

Borisovs

et al. 2020

PeerJ

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1,4-dihydropyridines (1,4-DHP) possess important biochemical and pharmacological properties, including antimutagenic and DNA-binding activity. The latter activity was first described for water-soluble 1,4-DHP with carboxylic group in position 4, the sodium salt of the 1,4-DHP derivative AV-153 among others. Some data show the modification of physicochemical properties and biological activities of organic compounds by metal ions that form the salts. We demonstrated the different affinity to DNA and DNA-protecting capacity of AV-153 salts, depending on the salt-forming ion (Na, K, Li, Rb, Ca, Mg). This study aimed to use different approaches to collate data on the DNA-binding mode of AV-153-Na and five other AV-153 salts. All the AV-153 salts in this study quenched the ethidium bromide and DNA complex fluorescence, which points to an intercalation binding mode. For some of them, the intercalation binding was confirmed using cyclic voltammetry and circular dichroism spectroscopy. It was shown that in vitro all AV-153 salts can interact with four DNA bases. The FTIR spectroscopy data showed the interaction of AV-153 salts with both DNA bases and phosphate groups. A preference for base interaction was observed as the AV-153 salts interacted mostly with G and C bases. However, the highest differences were detected in the spectral region assigned to phosphate groups, which might indicate either conformational changes of DNA molecule (B form to A or H form) or partial denaturation of the molecule. According to the UV/VIS spectroscopy data, the salts also interact with the human telomere repeat, both in guanine quadruplex (G4) and single-stranded form; Na and K salts manifested higher affinity to G4, Li and Rb –to single-stranded DNA.

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Section: Discussionmentioning

confidence: 99%

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Ļeonova

Shvirksts

Borisovs

et al. 2020

PeerJ

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“…The results show that TTTMB and polymer 2 exhibit no inhibitory effect on -amylase. The result of 2 is different to that of reported zinc complexes which indicates the preference for mild -amylase inhibitory activity (Sneha Jose et al, 2018;Philip et al, 2017). The -amylase inhibition percentages of polymer 1 and the standard are presented in Fig.…”

Section: A-amylase Inhibitory Assaymentioning

confidence: 74%

“…Compared with polymer 2, the Cd II polymer possesses better inhibitory activity than the Zn II polymer. This may be because different metal ions affect their ability to bind to the O atoms of enzymes (Philip et al, 2017;Wang et al, 2019). Polymers 1 and 2 are isostructural, however, their different inhibition efficiency on -amylase indicates that the metal ions play important roles in the biological activity of CPs.…”

Section: A-amylase Inhibitory Assaymentioning

confidence: 99%

Synthesis, crystal structure and biological properties of Cd and Zn coordination polymers based on a flexible tripodal ligand

Wang

Ling

et al. 2019

Acta Crystallogr C

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Two new coordination polymers, namely poly[[hexathiocyanatotetrakis{μ3‐2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene}tricadmium(II)] 3.5‐hydrate], {[Cd3(SCN)6(C18H21N9)4]·3.5H2O}n (1), and poly[[hexathiocyanatotetrakis{μ3‐2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene}trizinc(II)] 3.5‐hydrate], {[Zn3(SCN)6(C18H21N9)4]·3.5H2O}n (2), have been synthesized under hydrothermal conditions and characterized by elemental analysis, IR spectroscopy and single‐crystal X‐ray diffraction analysis. From the X‐ray analysis, it is noteworthy that polymers 1 and 2 are isostructural, with their three‐dimensional structures composed of three kinds of four‐connection metal ions and two kinds of three‐connection 2,4,6‐trimethyl‐1,3,5‐tris[(triazol‐1‐yl)methyl]benzene (TTTMB) ligand nodes. Each metal ion is six‐coordinated in a slightly distorted octahedral geometry. The antioxidant activity against DPPH (2,2‐diphenyl‐1‐picrylhydrazyl) and the antidiabetic activity against α‐amylase of the synthesized compounds were evaluated in vitro. The results of the DPPH free‐radical scavenging assay showed that polymers 1 and 2 exhibited strong antioxidant effects, with IC50 values of 3.81 and 2.56 mg ml−1, respectively. The IC50 value in the antidiabetic studies of polymer 1 was 3.94 mg ml−1, while polymer 2 exhibited no antidiabetic activity. Polymers 1 and 2 revealed different inhibitory activities on DPPH and α‐amylase, which indicated that the metal ions play important roles in the biological activity of coordination polymers. In addition, the solid‐state photoluminescence properties and thermal stability of 1 and 2 have been investigated.

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“…Chromones represent one of the most common naturally occurring oxygen heterocyclic systems appearing promising biological activities such as anti‐tobacco mosaic virus (TMV), [ 1 ] anticancer, [ 2,3 ] antitumor, [ 4 ] anti‐inflammatory, [ 5,6 ] antioxidant, [ 7 ] antimicrobial, [ 8 ] anti‐nematicidal, [ 9 ] antiproliferative, [ 10 ] antidiabetic, [ 11 ] neuroprotective, [ 12 ] anti‐HIV, [ 13 ] as well as inhibitors for potential Alzheimer's disease. [ 14 ] In addition, chromones are used as corrosion inhibitors for steel in hydrochloric acid.…”

Section: Introductionmentioning

confidence: 99%

Construction, characterization, and antimicrobial evaluation of the novel heteroannulated chromeno[2′′,3′′:6′,5′]pyrido[2′,3′‐d] [1,3] thiazolo[3,2‐a]pyrimidines

Ibrahim

Al‐Harbi

Allehyani

2020

Journal of Heterocyclic Chem

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The reaction of chromone‐3‐carbonitrile with thiobarbituric acid afforded 2‐thioxochromeno[3′,2′:5,6]pyrido[2,3‐d]pyrimidine‐4,6(1H,3H)‐dione, which utilized as a building block for construction of a novel heteroannulated compounds containing chromenopyridothiazolopyrimidine moiety. Reactions of the starting compound with a variety of bielectrophilic reagents namely; chloroacetonitrile, bromomalononitrile, 3‐chloropentanedione, ethyl 2‐chloro‐3‐oxobutanoate, phenacyl bromide, chloroacetic acid, dibromoethane, and oxalyl chloride afforded the first known chromenopyridothiazolopyrimidines. Cyclization of the starting compound with 2,3‐dichloroquinoxaline gave the linear hepta‐annulated chromenopyridopyrimidothiazoloquinoxaline. In addition, chromenopyridopyrimido thiazolopyrimidines were efficiently synthesized. The antimicrobial activity was evaluated for the prepared compounds and some of them seemed notable activity against the tested microorganisms. Analytical and spectral data confirmed the structures of the new products.

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Metal based biologically active compounds: Design, synthesis, DNA binding and antidiabetic activity of 6-methyl-3-formyl chromone derived hydrazones and their metal (II) complexes

Cited by 57 publications

References 52 publications

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Synthesis, crystal structure and biological properties of Cd and Zn coordination polymers based on a flexible tripodal ligand

Construction, characterization, and antimicrobial evaluation of the novel heteroannulated chromeno[2′′,3′′:6′,5′]pyrido[2′,3′‐d] [1,3] thiazolo[3,2‐a]pyrimidines

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