Ruthenium(III)–aminopolycarboxylato complexes active for the reduction of the N–N bond of hydrazine and phenylhydrazine in aqueous acidic media

Prakash, Raju; Ramachandraiah, G.

doi:10.1039/a908338c

Cited by 4 publications

(4 citation statements)

References 33 publications

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“…We therefore sought analogous ruthenium complexes that are less prone to oxidation/dimerization when in a formulated solution. This oxidation/dimerization does not appear to occur with AMD6221 probably because the pK a of the coordinated H 2 O molecule (pK a = 8.3) [40] is higher than that observed in AMD6245. Previously, we have shown that AMD6245 has a significantly higher plasma C max than AMD6221 (74.5 μg/mL vs. 11.6 μg/mL) accompanied by a slower plasma clearance (1.13 mL/h vs. 19.9 mL/h) when administered as a single intravenous injection (20 mg/kg) in rats.…”

Section: Introductionmentioning

confidence: 77%

Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Storr

Cameron²,

Gossage

et al. 2005

Eur J Inorg Chem

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In this study a series of Ru III complexes, chelated by analogues of ethylenediaminetetraacetic acid (edta) and diethylenetriaminepentaacetic acid (dtpa), were produced and tested for NO scavenging ability. Modifications to the edta and dtpa ligand frameworks were made in an effort to alter the reactivity, aqueous stability and pharmacokinetics of the resulting Ru III complexes. The X-ray structure of the nitrosyl complex 38 confirms that the Ru III complex 27 reacts with NO to form a linear {Ru-NO} [6] complex. The nitrosyl complex [C 15

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Section: Introductionmentioning

confidence: 77%

Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Storr

Cameron²,

Gossage

et al. 2005

Eur J Inorg Chem

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“…This complex has been prepared on up to a 150 g scale without encountering any problems, other than isolation of a higher yield. A similar complex, K[Ru(H 2 dtpa)Cl], was prepared previously; , however, as this is the potassium salt it was not suitable for pharmaceutical purposes. AMD6221 was characterized by standard analytical techniques including elemental analysis, IR spectroscopy, and electrospray ionization mass spectrometry.…”

Section: Synthesismentioning

confidence: 99%

“…AMD6221 was characterized by standard analytical techniques including elemental analysis, IR spectroscopy, and electrospray ionization mass spectrometry. Because the method of preparation is similar to that reported for K[Ru(H 2 dtpa)Cl], , a potassium analysis using inductively coupled plasma mass spectrometry (ICP-MS) was performed. The results of this test confirmed that neither potassium nor any other cation is present and that the formulation of AMD6221 is as suggested.…”

Section: Synthesismentioning

confidence: 99%

Ruthenium(III) Polyaminocarboxylate Complexes: Efficient and Effective Nitric Oxide Scavengers

et al. 2003

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The preparation of two Ru(III) polyaminocarboxylate complexes, AMD6245 and AMD6221, and their nitrosyl analogues, AMD6204, AMD6263, and AMD3689, is described. The compounds are characterized by IR, ES-MS, and (13)C and (15)N NMR spectroscopy where appropriate and cyclic voltammetry. The crystal structures for AMD6245, AMD6263, and AMD3689 are presented. AMD6245 (C(10)H(14)N(2)O(9)Ru) crystallized in the P2(1)/c space group with a = 8.4382(2) A, b = 8.8304(2) A, c = 17.6321(4) A, beta = 99.603(o), V = 1295.3(2) A(3), and Z = 4. AMD6263 (C(10)H(14)N(3)O(10)Ru) crystallized in the P2(1)/c space group with a = 9.9043(4) A, b = 13.1144(3) A, c = 12.0914(4) A, beta = 100.191(o), V = 1545.8(5) A(3), and Z = 4. AMD3689 (C(14)H(24.56)N(4)O(13.28)Ru) crystallized in the P1 space group with a = 8.838(2) A, b = 9.452(3) A, c = 13.419(4) A, alpha = 78.413(6)(o), beta = 75.804(6)(o), gamma = 73.562(6)(o), V = 1031.8(5) A(3), and Z = 2. The reaction of AMD6245 and AMD6221 with nitric oxide is investigated using EPR spectroscopy and stopped flow kinetics. Upon reaction with NO, a linear, diamagnetic [RuNO](6) complex is formed. The substitution reaction of AMD6245 with NO proceeds with a second-order rate constant of 2.24 x 10(7) M(-1) s(-1) at 7.3 degrees C (pH = 7.4; 50 mM phosphate buffer). The substitution reaction of AMD6221 with NO proceeds with a second-order rate constant of 3 x 10(5) M(-1) s(-1) at 20 degrees C (pH = 7.4; 50 mM phosphate buffered saline). The NO scavenging ability was assessed using a RAW264 murine macrophage assay by measuring the difference in nitrite produced between untreated control cells and treated cells. At 100 microM AMD6245 has [NO(2-)] = 12.5 microM less than the untreated cells and AMD6221 has [NO(2-)] = 37.6 microM less than the untreated cells. There is an insignificant difference in the amount of nitrite produced between AMD6263 or AMD3689 treated cells and untreated cells.

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“…The number of titratable protons in aqueous solutions of the examined complexes was determined on the basis of the moles of NaOH consumed per mole of the complex during potentiometric titration. 9 From the corresponding titration curves presented in Fig. 3, it can be concluded that within the pH range from 3.0?8.0, the examined complexes contain a single (complex 3), two (complex 4) or three (complexes 1 and 2) acidic groups.…”

Section: Resultsmentioning

confidence: 87%

Acid-base equilibria of the Zn(II) and Fe(III) complexes with condensation products of 2-acetylpyridine and the dihydrazide of oxalic and malonic acid

Dražić¹,

Popovic²,

Jelić

et al. 2009

JSCS

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Acid-base equilibria of Zn(II) and Fe(III) complexes with N',N'2-bis- [(1E)-1-(2-pyridyl)ethylidene]ethanedihydrazide (ligand L1) and N',N'2-bis[(1E)- -1-(2-pyridyl)ethylidene]propanedihydrazide (ligand L2), i.e., [Fe(L1)Cl2(H2O)], [Fe(L2)Cl(H2O)]2+, [Zn(L1)(H2O)3]+ and [Zn(L2)(H2O)2]2+, which expressed cytotoxic activity, were investigated in aqueous media. The equilibrium constants were determined potentiometrically at 25?C at a constant ionic strength of 0.10 mol/dm3 (Na2SO4). The results showed that at pH < 8 both the Fe(III) complexes studied here have three, while [Zn(L1)(H2O)3]+ and [Zn(L2)(H2O)2]2+ have one and two titratable protons, respectively. Based on the obtained values for the equilibrium constants, protonation schemes of the examined complexes are proposed.

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Ruthenium(III)–aminopolycarboxylato complexes active for the reduction of the N–N bond of hydrazine and phenylhydrazine in aqueous acidic media

Cited by 4 publications

References 33 publications

Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Ruthenium(III) Polyaminocarboxylate Complexes: Efficient and Effective Nitric Oxide Scavengers

Acid-base equilibria of the Zn(II) and Fe(III) complexes with condensation products of 2-acetylpyridine and the dihydrazide of oxalic and malonic acid

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Ruthenium(III)–aminopolycarboxylato complexes active for the reduction of the N–N bond of hydrazine and phenylhydrazine in aqueous acidic media

Cited by 4 publications

References 33 publications

RuIII Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

RuIII Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Ruthenium(III) Polyaminocarboxylate Complexes: Efficient and Effective Nitric Oxide Scavengers

Acid-base equilibria of the Zn(II) and Fe(III) complexes with condensation products of 2-acetylpyridine and the dihydrazide of oxalic and malonic acid

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Product

Resources

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Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers

Ru^III Complexes of Edta and Dtpa Polyaminocarboxylate Analogues and Their Use as Nitric Oxide Scavengers