Structure and biological evaluation of pyridine-2-carboxamidine copper(II) complex resulting from N′-(4-nitrophenylsulfonyloxy)2-pyridine-carboxamidoxime

Perontsis, Spyros; Geromichalos, George D.; Pekou, Anna; Hatzidimitriou, Antonios G.; Pantazaki, Αnastasia A.; Fylaktakidou, Konstantina C.; Psomas, George

doi:10.1016/j.jinorgbio.2020.111085

Cited by 13 publications

(6 citation statements)

References 87 publications

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“…The most prevalent protein in the body‘s plasma is called human serum albumin (HSA), and it regulates the fluid transport among different bodily organelles and determines the plasma oncotic pressure. Human serum albumin (HSA) and Bovine serum albumin (BSA) plays a vital role in drug transport, [65–67] metabolism and toxicity. Due to its structural similarity to human serum albumin, the interaction of metal complexes with the plasma protein BSA has been thoroughly investigated in the past [68–70] …”

Section: Resultsmentioning

confidence: 99%

1‐Benzyl‐1H‐indazol‐3‐ol Copper(II) Derivatives as Anticancer Agents: In‐vitro Interaction with DNA/BSA, DFT, Molecular Docking and Cytotoxicity on MCF7 Cells

Salimath,

Pathak

2024

ChemistrySelect

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A set of three copper(II) complexes C28H24CuN4O2 [CuL1], C24H22CuN4O [CuL2] and C26H22CuN4O [CuL3] incorporated with ligands 1‐benzyl‐1H‐indazol‐3‐ol, 2,2′‐bipyridyl and 1,10‐phenanthroline have been synthesized, characterized and subjected for biomedical applications. New copper(II) derivatives were characterized by FTIR, EPR and HRMS spectral tools. Cyclic voltammograms were recorded to ascertain redox potential and UV‐Vis and Fluorometer were employed to establish photophysical properties of all the new copper(II) complexes. Further, these derivatives of Cu(II) were subjected for DNA and BSA binding studies by using absorption‐emission spectral methods and viscosity measurements as well as by molecular docking. DFT studies of the above‐mentioned derivatives suggested square planar geometry along with other relevant molecular investigations. Eventually, these new Cu(II) complexes have been tested with DPPH and MTT assay to determine the cytotoxicity against MCF7 cell lines to observe remarkable potency with IC50 values 80.68 μg/ml, 49.40 μg/ml and 45.91 μg/ml, respectively.

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Section: Resultsmentioning

confidence: 99%

1‐Benzyl‐1H‐indazol‐3‐ol Copper(II) Derivatives as Anticancer Agents: In‐vitro Interaction with DNA/BSA, DFT, Molecular Docking and Cytotoxicity on MCF7 Cells

Salimath,

Pathak

2024

ChemistrySelect

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“…[93b,115] The Cu(I) based complex, 203 with 2-aminopyridine is a stable complex owing to the chelating behaviour of two similar ligands attached to the metal ion. [116] Copper complexes of nicotinic acid and 2-substituted py 204 exhibits promising superoxide dismutase (SOD) activity with IC 50 49.07 μM. Additionally the compound shows greater antimicrobial activity against B. subtilis and C. albicans, at concentration level 256 μgmL À 1 (ampicillin as standard was used with inhibitory efficiency of 25 μgmL À 1 ) [117] In the same report other derivatives showed mild efficiency against the [a]Activity of compound is expressed as ZI [mm] [b] Activity is shown for complexes bearing X=O and counter ion ClO 4 À and OTf.…”

Section: Coordination Compounds For Biological Applicationsmentioning

confidence: 99%

“…A cationic complex of bidentate py derived ligand, 207 was found very active against representative gram negative and positive strains (E. coli, X. campestris and S. aureus, B. cereus, B. subtilis). [116] The activity was compared with reference compound, enrofloxacin and it came out that these compounds exhibited selective efficiency against gram negative bacterial strains. The binding power of the compounds was explored and was found that they bind tightly and reversibly to serum albumins.…”

Section: Coordination Compounds For Biological Applicationsmentioning

confidence: 99%

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Khan

2021

ChemistrySelect

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Pyridine (py) is an important heterocyclic compound and is an integral part of various natural products. There are various medicines containing py ring system being available in the market to combat different human ailments. Observing the medicine market, Omeprazole, a widely used py-based drug in medicinal market since 1998. Netupitant (an antiemitic drug, since 2014) is used in combination with another drug to prevent acute and delayed vomiting and nausea associated with cancer chemotherapy led the run towards development of anticancer drugs. Several drugs have been approved by FDA for the treatment of cancer in recent years such as, Abemaciclib (2015), Lorlatinib (2018), Apalutamide (2018) and Ivosidenib (2019). Research on py on the bases of these advancements is an evergreen field and associated with greater hopes to address several disease related issues. Several compounds are in the process of clinical trials and are expected to serve various purposes in days to come. This review article deals with recent findings in py chemistry and its coordination complexes. The medicinal efficiency has been argued for organic and inorganic derivatives. Selected biological applications are hereby discussed as follow up study of our report in 2015. Suitable literature prior to 2015 has also been incorporated in appropriate places in order to cover the scope in broader sense.

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“…These prototype materials can help us to figure out possibilities of the formation of similar metal complexes with other metals utilizing ligands which we used in this study. It is known that such ligands can form different types of chelate complexes using active N atoms in heterocycles and carboximidamide groups [16]. In addition, two different halogens, Cl and Br, were used for complex formation.…”

Section: Introductionmentioning

confidence: 99%

Interplay of Isomorphs and Polymorphs of Amidino-Copper(II) Complexes with Different Halides

Yamba,

Peoble,

Novikov

et al. 2024

Crystals

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To increase the number of potential materials for application as MRI contrast agents, several Cu(II) complexes were synthesized. Cu(II) complexes were chosen because they are less expensive in comparison with the presently used Gd(III), Mn(II) and other agents. Pyridine-2-carboximidamide (1), pyrimidine-2-carboximidamide (2) and pyrazole-2-carboximidamide (3) in the form of different salts along with CuCl2 and NaCl or CuBr2 and NaBr were used to obtain four Cu(II) complexes: dichloro-pyrimidine-2-carboximidamide copper(II) (4), dibromo-pyrimidine-2-carboximidamide copper(II) (5), dichloro-pirazole-2-carboximidamide copper(II) (6), and dibromo-pirazole-2-carboximidamide copper(II) (7). X-ray diffraction analysis revealed that molecular complexes 4–7 contain square planar coordinated Cu(II) atoms and their structures are very similar, as well as their packing in crystals, which allows us to consider them isomorphs. The same synthetic approach to complex preparation where NaCl or NaBr was not used brought us to the formation of dimeric complexes μ-chloro{chloro(pyridine-2-carboximidamide)copper(II)} (8) and μ-chloro{chloro(pyrimidine-2-carboximidamide)copper(II)} (9). In the dimeric complexes, two fragments which were the same as in monomeric complexes 4–7 are held together by bridging Cu-Cl bonds making the coordination of Cu equal to 5 (square pyramid). In dimeric complexes, axial Cu-Cl bonds are 2.7360 and 2.854 Å. These values are Cu-Cl bonds on the edge of existence according to statistical data from CSD. Synthesized complexes were characterized by IR spectroscopy, TGA, PXRD, EPR, and quantum chemical calculations. The higher thermal stability of monomer pyrimidine-based complexes with Cl and Br substituents makes them more prospective for further studies.

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Structure and biological evaluation of pyridine-2-carboxamidine copper(II) complex resulting from N′-(4-nitrophenylsulfonyloxy)2-pyridine-carboxamidoxime

Cited by 13 publications

References 87 publications

1‐Benzyl‐1H‐indazol‐3‐ol Copper(II) Derivatives as Anticancer Agents: In‐vitro Interaction with DNA/BSA, DFT, Molecular Docking and Cytotoxicity on MCF7 Cells

1‐Benzyl‐1H‐indazol‐3‐ol Copper(II) Derivatives as Anticancer Agents: In‐vitro Interaction with DNA/BSA, DFT, Molecular Docking and Cytotoxicity on MCF7 Cells

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Interplay of Isomorphs and Polymorphs of Amidino-Copper(II) Complexes with Different Halides

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