Synthesis, structure and cytotoxicity studies on diorganotin (R = Me, Et) complexes of N-methylpyridoxine (MePN, PN = Vitamin B6) containing different anions

Casas, José S.; Couce, Marı́a D.; Sánchez, Agustı́n; Sordo, José; López, Esperanza

doi:10.1016/j.jorganchem.2011.09.022

Cited by 11 publications

(5 citation statements)

References 40 publications

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“…Considering the Gd-O bond lengths involving alc groups, they show an average value of 2.360(1) Å, which is somewhat shorter than th the Gd-O bond lengths of water molecules [2.424(1) Å] (Table S1). S1) [8][9][10][11][12][13][14][15][16][17][18][19] these crystallographic data agree with those reported for other similar compou [27,30,31].…”

Section: Description Of the Crystal Structuresupporting

confidence: 89%

“…Finally, the -NH groups of pyridoxine molecules and chloride anion S1) [8][9][10][11][12][13][14][15][16][17][18][19]. All these crystallographic data agree with those reported for other similar compounds [27,30,31].…”

Section: Description Of the Crystal Structuresupporting

confidence: 84%

“…17.7(1) • . The C-C, C-N, and C-O bond lengths agree with those found in the literature for the pyridoxine molecule coordinated to different metal ions (TableS1)[8][9][10][11][12][13][14][15][16][17][18][19]. All these crystallographic data agree with those reported for other similar compounds[27,30,31].In the crystal of 1, the cationic [Gd(pyr) 2 (H 2 O) 4 ] 3+ entities are connected by means of H-bonding interactions generated by coordinated-water molecules and chloride anions, thus generating a 1D motif that grows along the crystallographic a axis [O1w•••Cl2a = 3.133(1) Å and O4w•••Cl2a = 3.147(1) Å; (a) = x + 1, y, z] (Figure 2).…”

supporting

confidence: 88%

“…Over more than four decades, pyridoxine has also been investigated as a suitable ligand toward the preparation of metal complexes. Its pyridinic nitrogen atom and alcohols groups have been used to coordinate several metal ions (Scheme 1), such as Cd II [7], Fe III [8], Co III [9], Cu II [9][10][11], Sn IV [12][13][14], and U VI [15][16][17][18][19][20]. In most cases, pyridoxine molecule chelates or bridges through its alcohols groups, in the form of alkoxide, phenolate, or just as alcohol functional groups, and only in a few systems the pyridinic nitrogen atom is involved in metal coordination [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

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A Gadolinium(III) Complex Based on Pyridoxine Molecule with Single-Ion Magnet and Magnetic Resonance Imaging Properties

Orts-Arroyo,

Ten-Esteve,

Ginés-Cárdenas

et al. 2024

IJMS

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Pyridoxine (pyr) is a versatile molecule that forms part of the family of B vitamins. It is used to treat and prevent vitamin B6 deficiency and certain types of metabolic disorders. Moreover, the pyridoxine molecule has been investigated as a suitable ligand toward metal ions. Nevertheless, the study of the magnetic properties of metal complexes containing lanthanide(III) ions and this biomolecule is unexplored. We have synthesized and characterized a novel pyridoxine-based GdIII complex of formula [GdIII(pyr)2(H2O)4]Cl3 · 2 H2O (1) [pyr = pyridoxine]. 1 crystallizes in the triclinic system and space group Pī. In its crystal packing, cationic [Gd(pyr)2(H2O)4]3+ entities are connected through H-bonding interactions involving non-coordinating water molecules and chloride anions. In addition, Hirshfeld surfaces of 1 were calculated to further investigate their intermolecular interactions in the crystal lattice. Our investigation of the magnetic properties of 1, through ac magnetic susceptibility measurements, reveals the occurrence of a slow relaxation in magnetization in this mononuclear GdIII complex, indicating an unusual single-ion magnet (SIM) behavior for this pseudo-isotropic metal ion at very low temperatures. We also studied the relaxometric properties of 1, as a potential contrast agent for high-field magnetic resonance imaging (MRI), from solutions of 1 prepared in physiological serum (0.0–3.2 mM range) and measured at 3 T on a clinical MRI scanner. The values of relaxivity obtained for 1 are larger than those of some commercial MRI contrast agents based on mononuclear GdIII systems.

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Section: Description Of the Crystal Structuresupporting

confidence: 89%

Section: Description Of the Crystal Structuresupporting

confidence: 84%

supporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Gadolinium(III) Complex Based on Pyridoxine Molecule with Single-Ion Magnet and Magnetic Resonance Imaging Properties

Orts-Arroyo,

Ten-Esteve,

Ginés-Cárdenas

et al. 2024

IJMS

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“…[1][2][3][4][5][6][7][8][9][10][11][12] It is noteworthy that, for a long time, organotin(IV) complexes have been widely used in a variety of industrial and agricultural applications. [1][2][3][4][5][6][7][8][9][10][11][12] It is noteworthy that, for a long time, organotin(IV) complexes have been widely used in a variety of industrial and agricultural applications.…”

Section: Introductionmentioning

confidence: 99%

Reactions of tin- and triorganotin(IV) isopropoxides with thymol derivative: Synthesis, characterization and in vitro antimicrobial screening

et al. 2013

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A new series of diisopropyloxytin- and triorganotin(IV) complexes of H2hbgl (1) of the general formula Sn(OPri)2(hbgl) (2), Sn(OPri)2(Hhbgl)2 (3), Ph3Sn(Hhbgl) (4), Bu3Sn(Hhbgl) (5) and Me3Sn(Hhbgl) (6), [where H2hbgl= a ligand of thymol derivative namely, N-(2-hydroxy-3-isopropyl-6-methyl benzyl)Glycine] were synthesized by reacting tin- and triorganotin(IV) chloride with the ligand, with the aid of sodium iso-propoxide in appropriate stiochiometric ratios (1:1 and 1:2). These complexes were characterized by elemental analysis, IR, 1H nuclear magnetic resonance. The spectral data suggest that the carboxylate group, in complexes 2-5, was bonded in a bidentate manner, while a unidentate bonding was observed in complex 6. All five complexes were tested in vitro for their antibacterial activity against Gram-positive bacteria namely, Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121 and two Gram-negative bacteria namely, Escherichia coli MTCC 1652 and Pseudomonas aeruginosa MTCC 741. All the five complexes were also tested against three pathogenic fungal strains namely, Aspergillus niger, A. flavus and Penicillium sp

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3‐(2‐Furyl)‐2‐sulfanylpropenoic Acid as a Chelating Agent for Lead(II) and Diorganonolead(IV) Compounds – Chemical Behaviour and In Vitro Protective Effect against Dimethyllead(IV) Toxicity

et al. 2012

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The reaction of the title acid (H2fspa) with lead(II) acetate and dimethyl‐ or diphenyllead(IV) acetate in alcoholic medium gives the 1:1 complexes [Pb(fspa)] and [PbR2(fspa)] (R = Me, Ph). When the reaction was carried out in the presence of diisopropylamine (Q), the [HQ]2[Pb(fspa)2] and [HQ]2[PbPh2(fspa)2] derivatives formed in low yield. Additionally, the compounds Na[PbMe2(OAc)3], [PbPh2(fspa)(DMSO)] and [PbPh2(fspa)(DMSO)]·DMSO were also isolated as crystalline solids in subsequent crystallization processes. All these compounds were characterized by IR and NMR (1H and 13C) spectroscopy and, in some cases, by X‐ray diffractometry and 207Pb NMR spectroscopy. Pig renal proximal tubule LLC‐PK1 culture cells were used to determine in vitro the nephroprotective effect of H2fspa, [HQ]2[Zn(fspa)2], vitamin B1 and vitamin B6 against PbMe2(NO3)2 toxicity. The beneficial effects of the acid, the zinc(II) complex and/or their combinations with vitamin B1 (thiamine nitrate) are described.

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Synthesis, structure and cytotoxicity studies on diorganotin (R = Me, Et) complexes of N-methylpyridoxine (MePN, PN = Vitamin B6) containing different anions

Cited by 11 publications

References 40 publications

A Gadolinium(III) Complex Based on Pyridoxine Molecule with Single-Ion Magnet and Magnetic Resonance Imaging Properties

A Gadolinium(III) Complex Based on Pyridoxine Molecule with Single-Ion Magnet and Magnetic Resonance Imaging Properties

Reactions of tin- and triorganotin(IV) isopropoxides with thymol derivative: Synthesis, characterization and in vitro antimicrobial screening

3‐(2‐Furyl)‐2‐sulfanylpropenoic Acid as a Chelating Agent for Lead(II) and Diorganonolead(IV) Compounds – Chemical Behaviour and In Vitro Protective Effect against Dimethyllead(IV) Toxicity

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