Cytostatic, mutagenic, antineoplastic activities and preliminar toxicity of copper (II) new drugs: Casiopeinas I, II, III.

Ruiz-Ramirez, Lena; Gracia-Mora, Isabel; Rosa, Ma.Esther de la; López, Héctor Sumano; Gomez, Celedonio; Arenas, Francisco; Gomez, Eusebio; Pimentel, Emilio; Cruces, M.P.

doi:10.1016/0162-0134(93)85435-b

Cited by 12 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, the Casiopeínas and Casiopeína-like compounds have a more reversible behavior than the one observed in our systems. This is in agreement with the higher flexibility of these ternary complexes where the phen and amino acid units are an independent set of ligands. − ,− …”

Section: Resultssupporting

confidence: 78%

“…Within these complexes, some combine the phen unit with amino acids as independent units forming ternary complexes. Namely, the copper complexes known as Casiopeínas, developed by Ruiz-Azuara and co-workers, − and Casiopeína-like compounds. − These complexes have the general formulas [Cu(N–N)(N–O)] + and [Cu(N–N)(O–O)] + , where N–N is an aromatic substituted diamine (phen, bipyridine and extended planar heterocyclic bases), N–O is an α- l -amino acidato and O–O is acetylacetonate or salicyaldehydate. Different amino acids have been tested, among them l -glycine, l -alanine, l -valine, l -leucine, l -isoleucine, l -proline, l -phenylalanine, l -tryptophan, l -tyrosine, l -threonine, l -methionine, l -ornitine, and l -arginine.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copper(II) Complexes of Phenanthroline and Histidine Containing Ligands: Synthesis, Characterization and Evaluation of their DNA Cleavage and Cytotoxic Activity

et al. 2016

View full text Add to dashboard Cite

Copper(II) complexes have been intensely investigated in a variety of diseases and pathological conditions due to their therapeutic potential. The development of these complexes requires a good knowledge of metal coordination chemistry and ligand design to control species distribution in solution and tailor the copper(II) centers in the right environment for the desired biological activity. Herein we present the synthesis and characterization of two ligands HL1 and HL2 containing a phenanthroline unit (phen) attached to the amino group of histidine (His). Their copper(II) coordination properties were studied using potentiometry, spectroscopy techniques (UV-vis and EPR), mass spectrometry (ESI-MS) and DFT calculations. The data showed the formation of single copper complexes, [CuL1] and [CuL2], with high stability within a large pH range (from 3.0 to 9.0 for [CuL1] and from 4.5 to 10.0 for [CuL2]). In both complexes the Cu ion is bound to the phen unit, the imidazole ring and the deprotonated amide group, and displays a distorted square pyramidal geometry as confirmed by single crystal X-ray crystallography. Interestingly, despite having similar structures, these copper complexes show different redox potentials, DNA cleavage properties and cytotoxic activity against different cancer cell lines (human ovarian (A2780), its cisplatin-resistant variant (A2780cisR) and human breast (MCF7) cancer cell lines). The [CuL2] complex has lower reduction potential (E= -0.722 V vs -0.452 V for [CuL1]) but higher biological activity. These results highlight the effect of different pendant functional groups (carboxylate vs amide), placed out of the coordination sphere, in the properties of these copper complexes.

show abstract

Section: Resultssupporting

confidence: 78%

Section: Introductionmentioning

confidence: 99%

Copper(II) Complexes of Phenanthroline and Histidine Containing Ligands: Synthesis, Characterization and Evaluation of their DNA Cleavage and Cytotoxic Activity

et al. 2016

View full text Add to dashboard Cite

show abstract

“…A preliminary report of antineoplastic activity was presented (7), also SOD like activity and the induction of apoptosis has been reported (8,9). Casiopefnas have shown cytotoxicity in several munne tumoral cell lines and strong in vivo antitumor activity in routine tumoral models in our preliminar results (10). qqae present study was designed to evaluate the in vitro antitumor activity of several Casiopeinas against various human and routine tumoral cell lines and to observe a correlation of activity as a function of the peripherical substituents on the ligands.…”

Section: Introductionmentioning

confidence: 58%

Knigth′s Move in the Periodic Table, From Copper to Platinum,Novel Antitumor Mixed Chelate Copper Compounds, Casiopeinas,Evaluated by an in Vitro Human and Murine Cancer Cell Line Panel

et al. 2001

Self Cite

View full text Add to dashboard Cite

We synthesized a novel anticancer agents based on mixed chelate copper (II) complexes, named Casiopeínas® has of general formula [Cu(N-N)(N-O)H2O]NO3 (where, N-N = diimines as 1,10- phenanthroline, 2,2-bipyridine, or substituted and N-O=aminoeidate or [Cu(N-N)(O-O)H2O]NO3 (where NN= diimines as 10-phenanthroline, 2,2-bipyridine or substituted Casiopeínas I, II, IV, V, VI, VII VIII and O-O=acetylacetonate, salicylaldehidate Casiopínas III). We evaluated the in vitro antitumor activity using a human cancer cell panel and some nurine cancer cells. Eleven Casiopeinas are evaluated in order to acquire some structure-activity correlations and some monodentated Casiopeinäs analogues; cisplatinum was used as control drug. The 50% growth inhibition observed is, in all cases reach with concentrations of Casiopeina's 10 or 100 times lower than cisplatinum. In a previous work we reported the induction of apoptosis by Casiopeina II. The results indicate that Casiopeinass are a promising new anticancer drug candidates to be developed further toward clinical trials.

show abstract

“…The electron donor-acceptor capacity of these compounds is compared with the electron donor-acceptor properties of other molecules which might be important in terms of cancer disease. These are the DNA nitrogen bases, the DNA nitrogen base pairs, certain free radicals which are responsible for oxidative stress and GSH which is apparently important as it is involved in the genotoxic activity of copper compounds [52][53][54][55][56][57][58]. The results are shown in Table 2.…”

Section: Resultsmentioning

confidence: 99%

“…For over two decades [50][51][52][53][54][55][56][57][58], new antineoplastic and genotoxic compounds were synthesized and reported. These substances are metal-based drugs named Casiopeínas ® and they are a series of mixed chelate copper complexes which are being evaluated as possible anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Do Casiopeinas® Prevent Cancer Disease by Acting as Antiradicals? A Chemical Reactivity Study Applying Density Functional Theory

Avelar

Martínez

2017

J. Mex. Chem. Soc.

View full text Add to dashboard Cite

The main goal of this investigation is to study the possible mechanisms of Casiopeinas® as anticancer agents. Electrodonating (χ-) and electroaccepting (χ+) electronegativity were calculated applying Density Functional Theory. Two different anticancer mechanisms of Casiopeínas® are proposed. There might be antiradical molecules preventing the formation of cancer cells or these molecules could reduce the amount of GSH and as a result over-produce free radicals, increasing the oxidative stress which in turn kills the cancer cells.

show abstract

Cytostatic, mutagenic, antineoplastic activities and preliminar toxicity of copper (II) new drugs: Casiopeinas I, II, III.

Cited by 12 publications

References 0 publications

Copper(II) Complexes of Phenanthroline and Histidine Containing Ligands: Synthesis, Characterization and Evaluation of their DNA Cleavage and Cytotoxic Activity

Copper(II) Complexes of Phenanthroline and Histidine Containing Ligands: Synthesis, Characterization and Evaluation of their DNA Cleavage and Cytotoxic Activity

Knigth′s Move in the Periodic Table, From Copper to Platinum,Novel Antitumor Mixed Chelate Copper Compounds, Casiopeinas,Evaluated by an in Vitro Human and Murine Cancer Cell Line Panel

Do Casiopeinas® Prevent Cancer Disease by Acting as Antiradicals? A Chemical Reactivity Study Applying Density Functional Theory

Contact Info

Product

Resources

About