Novel Co III complexes containing fluorescent coumarin-N-acylhydrazone hybrid ligands: Synthesis, crystal structures, solution studies and DFT calculations

Areas, Esther S.; Bronsato, Bruna J. da S.; Pereira, Thiago Moreira; Guedes, Guilherme P.; Miranda, Fabio S.; Kümmerle, Arthur Eugen; Cruz, Antonio Gerson Bernardo da; Neves, Adriana Freitas

doi:10.1016/j.saa.2017.06.031

Cited by 18 publications

(6 citation statements)

References 65 publications

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“…HL exhibited irreversible anodic (Ia*) and cathodic (Ic*) processes at –0.196 V and –1.82 V vs. Fc/Fc + , respectively, which were found within similar ranges reported for related compounds , . In the literature, reduction processes exhibited by coumarin and 1,3‐diketone compounds are frequently assigned to carbonyl reduction, which in our case would refer to lactone or β‐keto ester sub‐units.…”

Section: Resultssupporting

confidence: 83%

“…Coumarin derivatives containing the 7–N(Et) 2 and 7‐OH groups displayed absorptions around 350–430 nm, attributed to π → π* . Previous studies of coumarin–N–acylhydrazone hybrids and their corresponding Co III complexes showed the same type of transition in the region of 405–470 nm in phosphate buffer. Indeed, DFT calculations performed for the compounds confirmed that the band at 450 nm is related to the π → π* transition centered on the ligand (SI, Table S2).…”

Section: Resultsmentioning

confidence: 68%

“…The most unshielded hydrogen atom corresponded to H4 from the coumarin ring at δ = 8.78, which appeared at δ = 8.56 in the free ligand (SI, Figure S3). This downfield displacement is characteristic of coumarin‐metal complexes, while other aromatic hydrogen atoms from the coumarin ring (H5/H6/H8) did not move appreciably. Evidence of deprotonation and coordination as L –1 was observed by the large shift of the H11 signal from δ = 3.94 to δ = 6.31 in the spectrum, as reported previously for analogous complexes .…”

Section: Resultsmentioning

confidence: 90%

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Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

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The search for new Co III -based drug delivery systems has attracted considerable attention in recent years. In this work, two cobalt complexes with general formula [Co(L)Am](ClO 4 ) n were synthesized, in which L -= (ethyl-3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate), a coumarin--keto ester ligand, and Am is the auxiliary amine TPA (tris-(2-pyridylmethyl)amine) or Py 2 en (2-pyridylmethyl)-1,2diamine). Complexation reactions yielded [Co II (L)TPA]ClO 4 (1) and [Co III (L)Py 2 en](ClO 4 ) 2 (2), and the Co III complex (2) was investigated as a potential hypoxia-activated prodrug prototype.[a]

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Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 68%

Section: Resultsmentioning

confidence: 90%

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Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

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“…Likewise, the d-d bands observed for the Zn(II) complexes 4 and 8 at about 28 089-28 490 cm −1 and 32 154-32 679 cm −1 show that they belong to the intra-ligand charge transfer interactions. [40][41][42][43][44][45] The empirical formulae of the complexes suggest that the Zn(II) complexes also exhibit octahedral geometry.…”

Section: Electronic Spectra and Magnetic Properties Of The Complexesmentioning

confidence: 99%

DNA fastening and scission actions of Cu(II), Co(II), Ni(II) and Zn(II) complexes: synthesis, spectral characterization and cytotoxic study

Kumaravel¹,

Utthra²,

Raman³

2017

Applied Organom Chemis

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A heterocyclic compound, 2‐(aminomethyl)benzimidazole dihydrohydrochloride, was treated with nitrobenzaldehyde to form a Schiff base that was made to react with divalent metals. A co‐ligand, either 1,10‐phenanthroline or 2,2′‐bipyridine, was added to this mixture to obtain metal chelators of type [ML(co‐L)2]Cl2. They were in 1:1:2 stoichiometry ratio, which was characterized by various spectroscopic techniques that suggested an octahedral geometry around the central metal ions. These complexes were investigated for their binding affinities with calf thymus (CT) DNA, using various techniques, such as UV–Vis, viscosity, cyclic voltammetry (CV), etc. The binding interaction studies revealed intercalation as the possible binding mode of the complexes with the CT DNA. In addition, these complexes were screened for their antimicrobial potential and DNA denaturing tendencies using gel electrophoretic assay. The antimicrobial screening investigation showed that the complexes behaved as better antimicrobial agents than the ligand, especially, complex 5 shows exceptional activity even in the electrophoretic assay along with the antimicrobial efficacy. Moreover, complex 5 was able to denature the plasmid DNA better than the other compounds. All the compounds were screened for cytotoxic efficacy, and the IC50 values suggest that the compounds possess cytotoxic activity to some extent that is almost the same as the activity of cisplatin.

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“…Hydrazone-based molecular structures are ubiquitous in many research fields, such as medicinal chemistry [1], organic synthesis [2], supramolecular chemistry [3], metal-organic coordination [4], dyes [5], fluorescent sensors, and molecular machines [6], besides others applications [7]. Over the last decades, the popularity of hydrazone group has increased due to its easy and direct-obtaining synthesis, stability toward hydrolysis in comparison with imines, modularity, and mainly, functional diversity of C═N▬N useful in several fields (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Hydrazone-Based Small-Molecule Chemosensors

Pereira¹,

Kümmerle²

2020

Computational Biology and Chemistry

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The hydrazone functional group is widely applied in several fields. The versatility and large use of this chemotype are attributed to its easy and straightforward synthesis and unique structural characteristics which is useful for different chemical and biological purposes. Recently hydrazone scaffold has been widely adopted in the design of small-molecule fluorescent and colorimetric chemosensors for detecting metals and anions because of its corresponding non-covalent interactions. This chapter provides an overview of hydrazone-based fluorescent and colorimetric chemosensors for anions and metals of biological interest, with their representative rational designs in the last 15 years. We hope this chapter inspires the development of novel and powerful fluorescent and colorimetric chemosensors for a broad range of applications.

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Novel Co III complexes containing fluorescent coumarin-N-acylhydrazone hybrid ligands: Synthesis, crystal structures, solution studies and DFT calculations

Cited by 18 publications

References 65 publications

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

DNA fastening and scission actions of Cu(II), Co(II), Ni(II) and Zn(II) complexes: synthesis, spectral characterization and cytotoxic study

Hydrazone-Based Small-Molecule Chemosensors

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