Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins

Torre, Marı́a H.; Gambino, Dinorah; Araujo, Jeannette; Cerecetto, Hugo; González, Mercedes; Lavaggi, María Laura; Azqueta, Amaya; Ceráin, Adela López de; Vega, Antonio Monge; Abram, Ulrich; Costa-Filho, Antonio J.

doi:10.1016/j.ejmech.2004.11.012

Cited by 58 publications

(52 citation statements)

References 21 publications

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“…In the case of Fe-L2 the disappearance of the strong ν(N → O) band in the characteristic range was probably due to the fact that the uncoordinated N → O groups have additional interactions with other atoms from neighboring molecules, which form intermolecular bonds in the solid state. This behavior was previously observed in related copper complexes [9]. In addition changes in the ν(CN → O) bands were observed due to complexation.…”

Section: Ir Spectrasupporting

confidence: 64%

“…This is in accordance with the presence of a secondary amine formed by deprotonation of the primary amine as a consequence of the coordination with iron ion. This behavior was previously observed for vanadyl, palladium and copper complexes with this family of ligands, and for metal chelates with aromatic ligands involving the amino group in ortho position to the N-oxide [5][6][7][8][9][10]17,28]. Besides, the strong ν(N → O) band for the free ligands turned weak upon complexation indicating the coordination of one N → O group per ligand molecule keeping the other uncoordinated as shown in Fig.…”

Section: Ir Spectramentioning

confidence: 54%

“…Unfortunately, it was impossible to obtain single crystals adequate for a crystallographic study. Nevertheless, complexes could be adequately characterized in the same way as previously done for the reported copper, vanadium, palladium and iron compounds of this family of ligands by using a combination of several physicochemical methods [5][6][7][8][9][10]. Both complexes are neutral non conducting compounds in DMSO.…”

Section: Citotoxicity Assaymentioning

confidence: 66%

“…The IR spectra of both new complexes were compared with those of the free ligands and the previously reported Cu, V, Pd and Fe complexes [5][6][7][8][9][10]17]. So, taking into account our previous knowledge on vibrational behavior of 3-aminoquinoxaline-2-carbonitrile N 1 ,N 4 -dioxide derivatives metal complexes, vibration bands related with the ligand's coordination mode were tentatively assigned.…”

Section: Ir Spectramentioning

confidence: 99%

“…Part of our group has been involved in the synthesis and biological assessment of a large amount of quinoxaline 1,4-di-N-oxide derivatives, including some of their metal complexes [5][6][7][8][9][10]. Some of these organic derivatives have shown excellent M. tuberculosis growth inhibition values.…”

Section: Introductionmentioning

confidence: 99%

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Design of novel iron compounds as potential therapeutic agents against tuberculosis

Tarallo¹,

Urquiola²,

Monge³

et al. 2010

Journal of Inorganic Biochemistry

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Section: Ir Spectrasupporting

confidence: 64%

Section: Ir Spectramentioning

confidence: 54%

Section: Citotoxicity Assaymentioning

confidence: 66%

Section: Ir Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Design of novel iron compounds as potential therapeutic agents against tuberculosis

Tarallo¹,

Urquiola²,

Monge³

et al. 2010

Journal of Inorganic Biochemistry

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Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

Hassan

Sumrra

Raza

et al. 2020

Applied Organom Chemis

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Sulfonamide core‐based new ligands 4‐{[(2,4‐dihydroxyphenyl)methylidene]amino}benzene‐1‐sulfonamide as (L1) and 4‐[(2,4‐dihydroxyphenyl)methylidene]amino‐N‐(5‐methyl‐1,2‐oxazol‐3‐yl)benzene‐1‐sulfonamide as (L2) have been synthesized through condensation response and were characterized by their UV–Vis, FT‐IR, 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. The ligands were reacted with transition metals (V, Fe, Co, Ni, Cu, and Zn) to synthesize the metal complexes (1)–(12). The metal complexes were also characterized, based on their physical (color, solubility, yield and melting point, conductance, magnetic), spectral (UV–Vis, FT‐IR, LC–MS), and microanalytical (elemental) data. The bidentate ligands were coordinated with transition metal salts by exploiting the azomethine nitrogen and the hydroxyl group oxygen. The electronic spectra for the metal complexes suggested them to have square‐pyramidal geometry for their vanadyl complexes whereas all the remaining complexes to be octahedral. The optimized geometries of the ligands at their ground state energies were studied through density functional approach at the B3LYP/6‐31G** level. The electronic, molecular electrostatic potential (MEP), and chemical descriptive properties were also explored by first‐principle insights. A clear intramolecular charge transfer was witnessed by occupied molecular orbitals (HOMO) to unoccupied molecular orbitals (LUMO). In addition, all the products were then tested for their antimicrobial potential against four bacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae) and two fungal (Aspergillus flavus and Aspergillus niger) species. The synthetic products were also tested for their antioxidant and enzyme inhibition properties that gave the excellent results implying their bioactive nature. The screening results revealed the metal complexes to have enhanced bioactive actions in comparison with their respective ligands.

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Synthesis and Characterization of Thiol Containing Furoxan Derivatives as Coligands for the Preparation of Potential Bioreductive Radiopharmaceuticals

Cerecetto

González

Onetto

et al. 2006

Archiv der Pharmazie

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The synthesis and characterization of thiol-containing 1,2,5-oxadiazole N-oxide (TONO) derivatives and their use as monodentate coligands for the preparation of (99m)Tc complexes is presented. 3-Mercaptomethyl-4-phenyl-1,2,5-oxadiazol N(2)-oxide and 3-(4-mercaptophenylmethylidenhydrazinocarbonyloxymethyl)-4-phenyl-1,2,5-oxadiazol N(2)-oxide were successfully synthesized and combined with the tridentate ligand N,N-bis(2-mercaptoethyl)-N',N'-diethylethylenediamine (BMEDA) to prepare "3+1 mixed ligand" technetium complexes. The( 99m)Tc complexes were obtained in high yield and radiochemical purity using low concentration of ligand and coligand. An alternative procedure using a xantate and a disulphide precursor of 3-mercaptomethyl-4-phenyl-1,2,5-oxadiazol N(2)-oxide yielded the same complex. Biological evaluation of the potentiality of the( 99m)Tc complexes as bioreductive radiopharmaceuticals was performed in normal CD1 mice and in mice bearing induced sarcoma. Tumour uptake was moderate but tumour/soft tissue ratio was favourable. Although these results are encouraging, further development is still necessary in order to achieve higher tumour uptake and lower gastrointestinal activity.

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Novel Cu(II) quinoxaline N1,N4-dioxide complexes as selective hypoxic cytotoxins

Cited by 58 publications

References 21 publications

Design of novel iron compounds as potential therapeutic agents against tuberculosis

Design of novel iron compounds as potential therapeutic agents against tuberculosis

Design, facile synthesis, spectroscopic characterization, and medicinal probing of metal‐based new sulfonamide drugs: A theoretical and spectral study

Synthesis and Characterization of Thiol Containing Furoxan Derivatives as Coligands for the Preparation of Potential Bioreductive Radiopharmaceuticals

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