Coordination Compounds of M(II) Biometal Ions with Acid- Type Anti-inflammatory Drugs as Ligands – A Review

Krstić, Nebojša; Nikolic, RS; Stankovic, MN; Nikolic, NG; Dordevic, DM

doi:10.4314/tjpr.v14i2.21

Cited by 29 publications

(49 citation statements)

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“…The study of the interaction of bio-metal ion M(II) and O-donor ligand (used as a drug) is interesting for several important reasons: in order to achieve a uniform drug dosage and bio-distribution, monitoring its pharmacokinetic and excretion, better antimicrobial, antitumor and antiulcer activity, and reduction of undesirable effects of the drug. 1,2,3 According to the literature data, products of the interaction of M(II) ions with N-donor ligands were studied by the spectroscopic methods in order to obtain a pharmaceutical product with better pharmacological and antitumor effects. 4,5 In this paper, the interactions of Fe(II) and Mn(II) ions with an antitumor drug named capecitabine (CPC) were studied by FT-IR and UV/Vis spectroscopy and obtained products were closely defined.…”

Section: Introductionmentioning

confidence: 99%

"SYNTHESIS AND SPECTRAL CHARACTERIZATION OF Fe(II) AND Mn(II) COMPLEXES WITH ORAL FLUOROURACIL PRO-DRUG CAPECITABINE "

2017

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Malignant neoplasms are today one of the leading causes of death in the world. Their treatment is extremely complex and requires the application of various chemical compounds which leads to disruption of homeostasis in the human body. During a treatment, there is a possibility of complex formation with important bioelements, such as copper, iron, cobalt, manganese, and others in the biological system. This paper presents the results of possible formation of complexes between Fe(II) and Mn(II) ions and capecitabine (IUPAC name: pentyl 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetra-hydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl carbamate). This chemotherapeutic agent is often used for the treatment of different solid tumors including breast, colon, prostate, liver and gastrointestinal tract carcinoma. Spectroscopic methods (UV/Vis and FT-IR spectroscopy) were used in order to research specific compounds between CPC and metal ions that may be formed in human body under physiological and approximately physiological conditions. In addition, microscopic characterization and comparison of solid samples of capecitabine and products of interactions of CPC as a ligand with Fe(II) and Mn(II) ions have been performed. FT-IR spectra indicate the existence of interaction of these two divalent bio cations with CPC, i.e. their coordination through nitrogen and oxygen atoms of CPC. When UV spectra of pure ligand and model systems M(II)-CPC were compared, similar absorption bands were observed with absorption maxima at the same wavenumbers but lower absorbance values for model systems M(II)-CPC.

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Section: Introductionmentioning

confidence: 99%

"SYNTHESIS AND SPECTRAL CHARACTERIZATION OF Fe(II) AND Mn(II) COMPLEXES WITH ORAL FLUOROURACIL PRO-DRUG CAPECITABINE "

2017

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“…Thus, if a given NSAIDs-metal complex remains intact in the biological medium its biological target is [a] She is now a Postdoctoral Fellow of the National Scholarships Foundation of Greece-Siemens program with a fellowship of excellence. [11,14] Scheme 12.The anti-inflammatory effects of 9 {[Cu(asp) 2 ] 2 , Scheme 12} were also tested. Sotiris K. Hadjikakou was born in Famagusta, Cyprus.…”

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confidence: 99%

“…[11] The structural characteristics, medicinal/veterinary properties, superoxide dismutase (SOD) activity [SOD is an enzyme that catalyzes the dismutation of the superoxide (O 2 -) radical into both ordinary molecular oxygen (O 2 ) and hydrogen peroxide (H 2 O 2 ), thus being involved in the inflammation mechanism], anti-inflammatory, and ulcerogenic effects of Cu-NSAIDs have also been reviewed. [11] The structural characteristics, medicinal/veterinary properties, superoxide dismutase (SOD) activity [SOD is an enzyme that catalyzes the dismutation of the superoxide (O 2 -) radical into both ordinary molecular oxygen (O 2 ) and hydrogen peroxide (H 2 O 2 ), thus being involved in the inflammation mechanism], anti-inflammatory, and ulcerogenic effects of Cu-NSAIDs have also been reviewed.…”

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confidence: 99%

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Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

2016

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The nonsteroidal anti-inflammatory drugs (NSAIDs) make up a great group of drugs that provide benefits in the prevention of cancers. Coordinated metal ions with NSAIDs provide advantages over the drugs themselves. The metal complexes of NSAIDs display a range of biological activities quite often inaccessible to the original NSAID ligands. NSAIDs-metal complexes have molecular properties different from those of the parent drugs. Thus, if a given NSAIDs-metal complex remains intact in the biological medium its biological target is [a] She is now a Postdoctoral Fellow of the National Scholarships Foundation of Greece-Siemens program with a fellowship of excellence. Her research interests are mainly focused on bioinorganic chemistry and particularly on the evaluation of the anticancer properties of metal complexes by studying their interaction with intracellular molecules. Sotiris K. Hadjikakou was born in Famagusta, Cyprus. He graduated from the Chemistry 3049 dentate, bidentate, or bridge ligands in polynuclear complexes.Compounds of NSAIDs with biometals exhibit better pharmacological activity than free NSAIDs. [11] The structural characteristics, medicinal/veterinary properties, superoxide dismutase (SOD) activity [SOD is an enzyme that catalyzes the dismutation of the superoxide (O 2 -) radical into both ordinary molecular oxygen (O 2 ) and hydrogen peroxide (H 2 O 2 ), thus being involved in the inflammation mechanism], anti-inflammatory, and ulcerogenic effects of Cu-NSAIDs have also been reviewed. [5] The review concluded that the mode of action of the Cu-NSAIDs is similar to that of the traditional NSAIDs and the complexes reduced gastrointestinal toxicity. Moreover, the stabilities of Cu-NSAIDs complexes are a critical determinant of their activity and toxicity. [5] This review summarizes the complexes of NSAIDs: (i) acetylsalicylic acid, diflunisal, salicylic acid (salicylic acid derivatives, Scheme 1), (ii) diclofenac, indometacin, sulindac, tolmetin (arylalkanoic acid derivatives, Scheme 2), (iii) ibuprofen, ketoprofen, Scheme 1. Salicylic acid derivatives.Scheme 2. Arylalkanoic acid derivatives. MicroreviewScheme 3. Arylpropionic acid derivatives (profens).Scheme 4. N-Arylanthranilic acid (fenamic acids). 3050Scheme 5. Other acid derivatives.Scheme 6. Oxicams. MicroreviewScheme 7. Aniline and p-aminophenol derivatives.Scheme 8. Sulfonamides. Discussion Metal Complexes of NSAIDs Exhibiting Anti-Inflammatory or Analgesic ActivityMn II -, Fe II -, Co II -, Ni II -, and Zn II -Schiff base complexes that contain anthranilic acid and aldoses in the Schiff base component are four-coordinate in the anhydrous state with the general formula ML 2 [M = Mn II (1), Fe II (2), Co II (3), Ni II (4), and Zn II (5), Scheme 9]. They were tested for their in vivo biological activities. The stability of the complexes in DMSO solution was confirmed by 1 H NMR spectroscopy. The relative toxicities of the metal complexes were determined with albino Wistar male rats; the LD 50 values followed the trend Ni < Mn < Co < Fe < Zn, w...

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“…Encouragingly, some metal-NSAID complexes exhibit greater cytotoxicity than cisplatin. A recent comprehensive review It should be noted that several metal-NSAIDs have been previously reported, and their binding to biomolecules such as DNA and human serum albumin (HSA) has been well characterized using spectroscopic methods [48][49][50][51][52]. In general, metal-NSAID complexes display stronger binding to biomolecules than the corresponding free NSAID.…”

Section: Introductionmentioning

confidence: 99%

A Cancer Stem Cell Potent Cobalt(III)–Cyclam Complex Bearing Two Tolfenamic Acid Moieties

2017

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Cancer stem cells (CSCs) are thought to be responsible for cancer relapse. CSCs are a subtype of cancer cells with the ability to differentiate, self-renew, and form secondary or tertiary tumors. Current cancer treatments-including chemotherapy, radiation, and surgery-effectively remove bulk cancer cells but are unable to eliminate CSCs. Here, we present the synthesis, characterization, and anti-CSC properties of a cobalt(III)-cyclam complex bearing two tolfenamic acid moieties, 3. Notably, 3 displays sub-micromolar potency towards breast CSCs and bulk breast cancer cells. Detailed mechanistic studies show that 3 is taken up readily by breast CSCs, enters the nucleus, causes DNA damage, and induces caspase-dependent apoptosis. Furthermore, 3 inhibits cyclooxygenase-2 (COX-2) expression in CSCs. The mechanism of action of 3 is similar to that of a naproxen-appended cobalt(III)-cyclam complex, 1 recently reported by our group. The advantage of 3 over 1 is that it has the potential to remove whole tumor populations (bulk cancer cells and CSCs) with a single dose.

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Coordination Compounds of M(II) Biometal Ions with Acid- Type Anti-inflammatory Drugs as Ligands – A Review

Cited by 29 publications

References 57 publications

"SYNTHESIS AND SPECTRAL CHARACTERIZATION OF Fe(II) AND Mn(II) COMPLEXES WITH ORAL FLUOROURACIL PRO-DRUG CAPECITABINE "

"SYNTHESIS AND SPECTRAL CHARACTERIZATION OF Fe(II) AND Mn(II) COMPLEXES WITH ORAL FLUOROURACIL PRO-DRUG CAPECITABINE "

Non‐Steroidal Anti‐Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level

A Cancer Stem Cell Potent Cobalt(III)–Cyclam Complex Bearing Two Tolfenamic Acid Moieties

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