Silver(I) complexes with hydantoins and allantoin

Puszyńska-Tuszkanow, Mariola; Grabowski, Tomasz; Daszkiewicz, Marek; Wietrzyk, Joanna; Filip, Beata; Maciejewska, Gabriela; Cieślak‐Golonka, Maria

doi:10.1016/j.jinorgbio.2010.09.013

Cited by 52 publications

(25 citation statements)

References 30 publications

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“…[21] C Data derived from separate experiment. [38] The inhibitory activities of PC with CLA isomer residues at sn-2 and stearoyl at sn-1 (4c-e) and PC with CLA isomer residues at sn-1 and stearoyl at sn-2 (5c-e) were not significantly different to each other towards HL-60 and MCF-7. The HT-29 line showed greater sensitivity to mixed-chain PC with trans-10, cis-12 (4e, 4d) than cis-9,trans-11 CLA (5e, 5d) residues.…”

Section: Cytotoxic Studymentioning

confidence: 94%

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

et al. 2015

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Novel phosphatidylcholines and lysophosphatidylcholines with cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acid (CLA) were synthesized in high yields (75-99 %). The in vitro cytotoxic activities of these compounds against three human cancer cell lines (HL-60, MCF-7, and HT-29) were evaluated. The results revealed that there are differences in the activity between phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 CLA acyl groups. 1,2-Di(9Z,11E)octadecadienoyl-sn-glycero-3-phosphocholine was the most potent cytotoxic agent among all tested CLA derivatives and its IC 50 (concentration of a compound that inhibits the proliferation of 50 % of the cancer cell population) was 29.4 mM against HL-60. Moreover, phosphatidylcholines with CLA acyls exhibited much lower cytotoxicity against non-cancer cells (Balb/3T3) than free CLA isomers.

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Section: Cytotoxic Studymentioning

confidence: 94%

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

et al. 2015

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“…= 8500 cm -1 [46] and D[Ni(H 2 O) 2 L 2 ] = 10,160 cm -1 (this work, Table 4), a hypothetical D[Ni(sar) 6 ] 4-was found to be 10,990 cm -1 . This value locates sarcosine ligand in the spectrochemical series as follows: H 2 O (8500) \ py (10,150) \ NH 3 (10,750) \ 1-mhyd (10,750) \ sar (10,990) \ en (11,700) \ bpy (12,650).…”

Section: Electronic Spectramentioning

confidence: 71%

“…4b), the ring pattern R 2 2 (12) is created. It is connected to the relation 2ÁE 1 1 (6) HONiOCO = R 2 2 (12). It is worth noting that R 2 2 (12) ring and the second R 2 2 (8) ring result from doubling E 1 1 (6) HONiOCO and E 1 1 (4) HONiO pathways, respectively, due to inversion center located in both ring patterns.…”

Section: Crystal Structurementioning

confidence: 73%

“…1). Hydantoin and its derivatives at moderate temperature and pH form complexes with metal ions [10][11][12][13]. However, when elevated temperature and extreme pH are applied, hydantoins hydrolyze, forming in the most cases, amino acids [14].…”

Section: Introductionmentioning

confidence: 99%

“…Selected experimental frequencies in the IR and Raman spectra and the theoretical wavenumbers, m (cm -1 ), IR intensities, I IR (km mol -1 ), I R Raman intensities (arbitrary units) of [Ni(sar) 2 (H 2 O) 2 ] calculated at the PBE0 density functional NiO (41), dH-N-CH 3 (13), dC=O (12), m a NiN (11) NiO (31), dH-N-CH 3 (24), m s NiN(22), dC=O(12) …”

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confidence: 99%

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Ni(II) complex with sarcosine derived from in situ generated ligand: structural, spectroscopic, and DFT studies

et al. 2015

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Nickel(II) complex with sarcosine [Ni(sar) 2 (H 2 O) 2 ] (1) has been obtained as a reaction product of a system: Ni(II)Cl 2 -1-methylhydantoin. Basic hydrolysis of the organic substrate leads to in situ formation of sarcosine ligand, which coordinates to the metal ion. The isolated complex has been characterized by means of single crystal X-ray diffraction and spectroscopic studies (IR, Raman, and NIR-UV-Vis) supported with DFT calculations. Single crystal X-ray diffraction revealed that the nickel environment in [NiN 2 O 4 ] chromophore exhibited the geometry of a tetragonally elongated octahedron. Hydrogen bonds create two chain patterns which propagate along the main crystallographic directions a and b. It leads to the formation of a 2D network. Electronic spectra analysis showed that the nickel surroundings can be described as pseudooctahedral in solution and tetragonal in the solid state. Based on the calculated 10Dq parameter (10,990 cm -1 ), sarcosine ligand was located in the spectrochemical series close to ammonia. Comprehensive studies of the molecular structure and vibrational spectra of the title complex have been performed using UPBE0, unrestricted density functional method. The clear-cut assignment of the bands in FT-IR and Raman spectra of studied complex has been made on the basis of the calculated potential energy distribution. The Ni-L(sarcosine) stretching vibrations were assigned in Raman spectrum to the medium intensity band at 442 cm -1 .

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Ag(I)‐mediated hydrolysis of hydrazone to azine: Synthesis, X‐ray structure, and biological investigations of two new Ag(I)‐azine complexes

Elbadawy

Khalil

Al-Wahaib

et al. 2022

Applied Organom Chemis

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Reactions of 2‐(1‐hydrazonoethyl)pyridine with silver salts AgX (X = NO3¯ or ClO4¯) proceeded via the hydrolysis of the pyridine ligand and the formation of the dinuclear [AgL1]2(ClO4)2 (1) and [AgL1(NO3)]2 (2) complexes of the azine ligand, 1,2‐bis(1‐(pyridin‐2‐yl)ethylidene)hydrazine (L1). The structures of the obtained complexes were determined by single crystal X‐ray diffraction. The azine ligand (L1) is acting as a bidentate ligand and connects the two Ag‐sites via the pyridine and the azine nitrogen atoms. In complex 1, the Ag(I) ion is tetra‐coordinated, while in complex 2 the Ag(I) ion is penta‐coordinated due to the presence of additional interaction with one of the oxygen atoms of the nitrate ion. As a result, the azine ligand is significantly twisted in complex 2 compared to complex 1. The optimized geometries of three conformers of L1 were calculated using DFT calculations, and their kinetic and thermodynamic stability were analyzed. It was found that a free rotation of L1 is required prior to the chelation of the Ag(I) ion. The packing in complex 1 is controlled by H…H, O…H, and Ag…O interactions, but in complex 2, the O…H and N…H interactions are the most significant. Complex 2 has better antifungal activity against Aspergillus fumigatus and Candida albicans than the antifungal drug Ketoconazole. Also, the nitrato complex 2 has a promising antioxidant activity compared to the perchlorate complex 1. The cytotoxicity against colon carcinoma HCT‐116 cell line is higher for complex 1 (IC50 = 19.72 ± 0.94 μg/ml) than complex 2 (IC50 = 68.31 ± 2.97 μg/ml).

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Silver(I) complexes with hydantoins and allantoin

Cited by 52 publications

References 30 publications

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies

Ni(II) complex with sarcosine derived from in situ generated ligand: structural, spectroscopic, and DFT studies

Ag(I)‐mediated hydrolysis of hydrazone to azine: Synthesis, X‐ray structure, and biological investigations of two new Ag(I)‐azine complexes

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