Metal complexes of anthranilic acid derivatives: A new class of non-competitive α-glucosidase inhibitors

Zheng, Jingwei; Ma, Lin

doi:10.1016/j.cclet.2016.01.052

Cited by 24 publications

(6 citation statements)

References 27 publications

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“…N and O electron-donor atoms and carbonyl group assembled to a cyclic system are considered suitable for efficient interactions with metal cations. These binding moieties are present in some biological relevant compounds such as the tetracycline, 28 3-hydroxy flavonoids, 29 and anthranilic acid, 30 all of which have chelating properties. Thus, we designed the APH compounds as bidentate ligands to interact with the metal anions guest via a potential metal-binding site formed by the lactam group and the exocyclic nitrogen atom, hypothesizing that the substituents R on the nitrogen atom at C-7 position could modulate the affinity of the nitrogen atom for metals ( Figure 1 ).…”

Section: Results and Discussionmentioning

confidence: 99%

Neuroprotective Action of Multitarget 7-Aminophenanthridin-6(5H)-one Derivatives against Metal-Induced Cell Death and Oxidative Stress in SN56 Cells

Moyano

Vicente-Zurdo

Blázquez-Barbadillo

et al. 2021

ACS Chem. Neurosci.

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Neurodegenerative diseases have been associated with brain metal accumulation, which produces oxidative stress (OS), matrix metalloproteinases (MMPs) induction, and neuronal cell death. Several metals have been reported to downregulate both the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway and the antioxidant enzymes regulated by it, mediating OS induction and neurodegeneration. Among a recently discovered family of multitarget 7-amino-phenanthridin-6-one derivatives ( APH ) the most promising compounds were tested against metal-induced cell death and OS in SN56 cells. These compounds, designed to have chelating activity, are known to inhibit some MMPs and to present antioxidant and neuroprotective effects against hydrogen peroxide treatment to SN56 neuronal cells. However, the mechanisms that mediate this protective effect are not fully understood. The obtained results show that compounds APH1 , APH2 , APH3 , APH4 , and APH5 were only able to chelate iron and copper ions among all metals studied and that APH3 , APH4 , and APH5 were also able to chelate mercury ion. However, none of them was able to chelate zinc, cadmium, and aluminum, thus exhibiting selective chelating activity that can be partly responsible for their neuroprotective action. Otherwise, our results indicate that their antioxidant effect is mediated through induction of the Nrf2 pathway that leads to overexpression of antioxidant enzymes. Finally, these compounds exhibited neuroprotective effects, reversing partially or completely the cytotoxic effects induced by the metals studied depending on the compound used. APH4 was the most effective and safe compound.

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Section: Results and Discussionmentioning

confidence: 99%

Neuroprotective Action of Multitarget 7-Aminophenanthridin-6(5H)-one Derivatives against Metal-Induced Cell Death and Oxidative Stress in SN56 Cells

Moyano

Vicente-Zurdo

Blázquez-Barbadillo

et al. 2021

ACS Chem. Neurosci.

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“…The regulation of the activity of α‐glucosidases by rationally designed compounds prove therapeutically efficient in the treatment of obesity, diabetes mellitus, metastatic cancers, and immunodeficiency virus infections (Hedrington & Davis, 2019). Zheng and Ma (2016) reported the metal complexes of the derivatives anthranilic acid 36–37 a–g (Figure 8) as a new class of non‐competitive inhibitors of α‐glucosidase. The in vitro analysis suggested a superior biological profile for the ligand complexes as compared to free ligands and metal ions.…”

Section: Antidiabetic Compounds Based On Anthranilic Acid Analoguesmentioning

confidence: 99%

Medicinal chemistry of anthranilic acid derivatives: A mini review

Prasher

Sharma

2021

Drug Development Research

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Anthranilic acid and its analogues present a privileged profile as pharmacophores for the rational development of pharmaceuticals deliberated for managing the pathophysiology and pathogenesis of various diseases. The substitution on anthranilic acid scaffold provides large compound libraries, which enable a comprehensive assessment of the structure activity relationship (SAR) analysis for the identification of hits and leads in a typical drug development paradigm. Besides, their widespread applications as anti‐inflammatory fenamates, the amide and anilide derivatives of anthranilic acid analogues play a central role in the management of several metabolic disorders. In addition, these derivatives of anthranilic acid exhibit interesting antimicrobial, antiviral and insecticidal properties, whereas the derivatives based on anthranilic diamide scaffold present applications as P‐glycoprotein inhibitors for managing the drug resistance in cancer cells. In addition, the anthranilic acid derivatives serve as the inducers of apoptosis, inhibitors of hedgehog signaling pathway, inhibitors of mitogen activated protein kinase pathway, and the inhibitors of aldo‐keto reductase enzymes. The antiviral derivatives of anthranilic acid focus on the inhibition of hepatitis C virus NS5B polymerase to manifest considerable antiviral properties. The anthranilic acid derivatives reportedly present neuroprotective applications by downregulating the key pathways responsible for the manifestation of neuropathological features and neurodegeneration. Nevertheless, the transition metal complexes of anthranilic acid derivatives offer therapeutic applications in diabetes mellitus, and obesity by regulating the activity of α‐glucosidase. The present review demonstrates a critical analysis of the therapeutic profile of the key derivatives of anthranilic acid and its analogues for the rational development of pharmaceuticals and therapeutic molecules.

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“…It has been reported that anthranilic acid derivatives exhibit anti-bacterial activities [ 26 ], and anti-inflammatory [ 27 ]. Some derivatives, such as N-phenylanthranilic acid, are employed as pharmacological precursor for the synthesis of anti-neoplastic, anti-inflammatory, anti-malarial [ 28 ] and α-glucosidase inhibitors [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of metal anthranilate complexes: catalytic and antipathogenic studies

et al. 2022

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Background Anthranilic acid is an active compound with diverse biological activities such as anti-inflammatory, antineoplastic, anti-malarial and α-glucosidase inhibitory properties. It can also chelate transition metals to form complexes with applications as antipathogens, photoluminescent materials, corrosion inhibitors, and catalysts. Results Anthranilic acid complexes (1–10) of Zn(II), Bi(III), Ag(I), Fe(II), Co(II), Cu(II), Mn(II), Al, Ni(II), and Cr(III) were synthesized and characterized using thermogravimetric (TGA), elemental analysis, FT-IR, UV–vis spectrometry, mass spectrometry and magnetic susceptibility. The morphology and size of metal complex (1–10) particles were determined by scanning electron microscope (SEM) and the surface area was determined by BET analysis. TGA and CHN analysis data indicated that the stoichiometries of complexes were 1:2 metal/ligand except for Ag(I), Al and Bi. Furthermore, DFT study was performed to optimize the structure of selected complexes. The complexes (1–10) were evaluated for their catalytic activity in the reduction of 4-nitrophenol (4-NP), antibacterial activity against S. aureus, P. aeroginosa and E. coli as well as their antifungal activity against F. solani and A. niger. The complexes were also tested against the second-stage juveniles (J2) root-knot nematodes. Conclusion Co(II) complex 5 and Cu(II) complex 6 showed high catalytic activity for the reduction of 4-NP to 4-aminophenol (4-AP). Ag(I) complex 3 showed the best activity against the pathogens that were tested namely clinically important bacteria S. aureus, P. aeroginosa and E. coli, commercially important fungi F. solani and A. niger and J2 root-knot nematodes M. javanica.

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Metal complexes of anthranilic acid derivatives: A new class of non-competitive α-glucosidase inhibitors

Cited by 24 publications

References 27 publications

Neuroprotective Action of Multitarget 7-Aminophenanthridin-6(5H)-one Derivatives against Metal-Induced Cell Death and Oxidative Stress in SN56 Cells

Neuroprotective Action of Multitarget 7-Aminophenanthridin-6(5H)-one Derivatives against Metal-Induced Cell Death and Oxidative Stress in SN56 Cells

Medicinal chemistry of anthranilic acid derivatives: A mini review

Synthesis of metal anthranilate complexes: catalytic and antipathogenic studies

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