Synthesis and X-ray crystal structure of tris(1,2-dimethyl-3-hydroxypyrid-4-onato)iron(III)

Charalambous, J.; Dodd, Azita; McPartlin, Mary; Matondo, Simba O.C.; Pathirana, Navin D.; Powell, Harold R.

doi:10.1016/s0277-5387(00)81813-6

Cited by 46 publications

(37 citation statements)

References 5 publications

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“…All of the amide protons point outwards from the molecule, but in the Fe-NTAA C H T U N G T R E N N U N G (BuHP) 3 complex one of them is pointing inwards and forms an intramolecular hydrogen bond with a chelating carbonyl O-atom from the neighbouring arm (hydrogen-bond length NH···O 2.23 ; hydrogen-bond angle N-H-O 1708). This type of intramolecular hydrogen bond is quite often found in this family of complexes [37] and in the NTA derivative it can be due to the higher number of hydrogen-bond donors and acceptors in a closer distance as well as to the higher flexibility of the HP arm, relative to the NTP derivative. The oxygen atom participation in that hydrogen bond should result in a change in its electronegativity, thus justifying the lengthening of the corresponding OÀFe bond (1.999 ), compared with the average value (1.950 ) found in these complexes, although still in the range of values reported in the literature for the X-ray crystal structure of the ferric complex with other 3-hydroxy-4-pyridinones (DFP).…”

Section: Wwwchemeurjorgmentioning

confidence: 85%

“…The oxygen atom participation in that hydrogen bond should result in a change in its electronegativity, thus justifying the lengthening of the corresponding OÀFe bond (1.999 ), compared with the average value (1.950 ) found in these complexes, although still in the range of values reported in the literature for the X-ray crystal structure of the ferric complex with other 3-hydroxy-4-pyridinones (DFP). [37] Since both complexes under study have the same number and type of atoms, their stability can be compared on the basis of differences between their total energies. The calculated minimum energies are very close (but (Fe-NTP-A C H T U N G T R E N N U N G (PrHP) 3 is slightly more stable than Fe-NTAA C H T U N G T R E N N U N G (BuHP) 3 ; DE = 0.004718 hartree = 2.960 kcal mol À1 ), thus suggesting analogous stabilities for both complexes.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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New Tris(hydroxypyridinones) as Iron and Aluminium Sequestering Agents: Synthesis, Complexation and In Vivo Studies

Chaves¹,

Marques²,

Matos³

et al. 2010

Chemistry A European J

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Two new tripodal tris(3-hydroxy-4-pyridinone) hexadentate chelators-NTA(BuHP)(3) and NTP(PrHP)(3) (NTA=nitrilotriacetic acid, NTP=nitrilotripropionic acid, HP=hydroxypyridone)-have been developed and studied in solution for their iron and aluminium binding affinity, and also assayed in vivo for their capacity to remove metal from an animal model that is overloaded. These chelators are positional isomers, possessing identical general structures based on aminotricarboxylic acid skeletons attached to three bidentate 3-hydroxy-4-pyridinones (3,4-HPs), but differing in the position of the amide linkage along the chelating "arm". In spite of expected differences in the tripodal ligands, such as acidity and hydrogen-bonding networks, they share important properties, namely, a mild hydrophilic character (log P ca. -1.2 to -1.4) and a strong chelating affinity for Fe and Al (pFe=27.9 and pAl=22.0 for NTA(BuHP)(3); pFe=29.4 and pAl=22.4 for NTP(PrHP)(3)). They also evidenced identical effects on the biodistribution and on the excretion of a radiotracer ((67)Ga) previously administered to mice, as models of iron overload animals. Comparison of the new compounds with reported analogues shows good improvement in terms of solution and in vivo sequestering properties, thus giving support to expectations about their potential clinical application as metal removal agents.

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Section: Wwwchemeurjorgmentioning

confidence: 85%

Section: Wwwchemeurjorgmentioning

confidence: 99%

New Tris(hydroxypyridinones) as Iron and Aluminium Sequestering Agents: Synthesis, Complexation and In Vivo Studies

Chaves¹,

Marques²,

Matos³

et al. 2010

Chemistry A European J

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“…Research in these laboratories has focussed on the development of ligands which will bind effectively to these metals, both in vitro and in vivo. In the course of this work, a series of pyridinonato metal complexes with unexpected and novel crystallographic properties was discovered (4)(5)(6)(7)(8).…”

Section: Introductionmentioning

confidence: 99%

“…lo), formed tris(ligand)metal(III) dodecahydrate complexes when the N-substituent was methyl or ethyl (the complexes M ( d~p )~ and M ( m e~p )~) (4)(5)(6)(7)(8). These crystallized in a manner unknown amongst inorganic hydrates; unusual hydrogen bonding was observed in the solid state.…”

Section: Introductionmentioning

confidence: 99%

1-n-Propyl- and 1-n-butyl-3-hydroxy-2-methyl-4-pyridinone complexes of group 13 (IIIA) metal ions

Simpson¹,

Rettig²,

Trotter³

et al. 1991

Can. J. Chem.

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. Can. J. Chem. 69, 893 (1991). The aluminum, gallium, and indium tris(1igand) complexes of 3-hydroxy-2-methyl-1-n-propyl-4-pyridinone and l-tz-butyl-3-hydroxy-2-methyl-4-pyridinone have been prepared and characterized. All six compounds were prepared in a one-pot synthesis from maltol, n-propyl-, or n-butylamine and an appropriate metal(II1) salt, and were completely characterized (IR, FAB-MS, 'H NMR, ' '~1 NMR, elemental analysis). Three of the six complexes were studied by single-crystal X-ray diffraction and were found to form trihydrates, unlike their 1-methyl and 1-ethyl analogues, which formed dodecahydrates. The n-butylpyridinone complex A1(CIOH14N02)3.3H20 (Al(nbp)3.3H2O) and 11-propylpyridinone complexes A1(C9H12N02)3.3H20 (A l ( n~p )~. 3 H~O ) , and Ga(C9H12N02)3.3H20 ( G a ( n p~)~. 3 H~O ) were essentially isostructural, crystallizing in the space group On a prCparC et caractiris6 les complexes tricoordinks de l'aluminium, du galliumet de l'indium avec la 3-hydroxy-2-mkthyll-n-propyl~pyridin-4-one et la 1-11-butyl-3-hydroxy-2-mithyl-pyridin-4-On a prepare les six composCs par des synthkses "bouillabaisses" impliquant le maltol, les tz-propyl-ou n-butyl-amines et le sel mCtallique(II1) appropriC et on les a caractCrisks compl&tement par ir, sm-bar, rmn du 'H, rmn du "Al et analyse ClCmentaire. On a examine trois des six complexes par diffraction des rayons-X par des cristaux uniques et on a trouvC qu'ils forment des trihydrates alors que leurs analogues I-mkthyle et 1-Cthyle foment des dodCcahydrates. Le complexe de la n-butylpyridinone, A1(CloH14N02)3.3H20 ( A l ( n b~)~. 3 H~O ) et les complexes de la n-propylpyridinone, A1(C9H12N02)3.

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“…Since the carbonyl group on the pyridinone ring is an electron draw group, the greater the electron density on the pyridinone ring donated by alkyl groups (ethtyl > methyl), the longer the carbonyl bond length should be. Interestingly, the carbonyl bond distance of EHEMHP is close to that of the iron-L1 complex [370]. In the complex, the corresponding carbonyl bond length is 1.299(8) Å .…”

Section: Preparation Of Iron Chelators With Functional Groups For Parmentioning

confidence: 77%

Nanoparticles for the Treatment ofAlzheimer's Disease: Theoretical Rationale, Present Status and Future Perspectives

Liu

Men

Perry

et al. 2003

Nanotechnologies for the Life Sciences

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The sections in this article are Introduction Rationales: The Ability of Nanoparticles to Cross the BBB – A Useful Tool to Deliver Drugs into the Brain Physiological Functions of the BBB Strategies for Drug BBB Penetration Preparation of Polymeric Nanoparticulate Drug Delivery Systems Possible Mechanisms by which Nanoparticles Cross the BBB Status: Nanoparticle Targeting Transport of Therapeutic Agents for Potential Treatment of AD Nanoparticle Targeting of A β to Deliver Potentially Therapeutic Agents Nanoparticulate Antioxidant Delivery to Increase Efficacy against A β‐mediated Oxidative Stress Nanoparticle Delivery of Copper Chelator for Preventing and Reversing A β Deposition Nanoparticle Transport of Iron Chelators and Metal Chelator Complexes Into and Out of the Brain, Respectively Increased Levels of Various Metals in the Brain of AD Patients Problems with Iron Chelators for Simultaneous Removal of Multimetal Ions for Treatment of AD Nanoparticle Transport Technology to Improve Chelation Therapy for AD Experimental Descriptions Results and Discussion Perspectives Acknowledgments

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Synthesis and X-ray crystal structure of tris(1,2-dimethyl-3-hydroxypyrid-4-onato)iron(III)

Cited by 46 publications

References 5 publications

New Tris(hydroxypyridinones) as Iron and Aluminium Sequestering Agents: Synthesis, Complexation and In Vivo Studies

New Tris(hydroxypyridinones) as Iron and Aluminium Sequestering Agents: Synthesis, Complexation and In Vivo Studies

1-n-Propyl- and 1-n-butyl-3-hydroxy-2-methyl-4-pyridinone complexes of group 13 (IIIA) metal ions

Nanoparticles for the Treatment ofAlzheimer's Disease: Theoretical Rationale, Present Status and Future Perspectives

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