N-Carboxyalkyl derivatives of 3-hydroxy-4-pyridinones: synthesis, complexation with Fe(III), Al(III) and Ga(III) and in vivo evaluation

Santos, M. Amélia; Gil, Marco; Marques, Sérgio M.; Gano, Lurdes; Cantinho, Guilhermina; Chaves, Sı́lvia

doi:10.1016/s0162-0134(02)00483-x

Cited by 56 publications

(97 citation statements)

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“…35.92 32.62 À1.03 [18] pM [c] 19.3 [19] 16.0 [19] [a] Values determined in 3 % DMSO. At physiological pH, the predominant form for both compounds is the neutral species H 3 L (ca.…”

Section: 45(4) 894(4)mentioning

confidence: 99%

“…The stability constants calculated herein for the M 3 + complexes are presented in Table 1, together with values previously determined for the Kemp derivatives [15] and DFP. [17][18][19] Data analysis of the electronic spectra obtained for the Figure 2, Figure 2, bottom, containing the species distribution curves for the proposed equilibrium model merged with some experimental spectral data, that is, the absorptivity at two characteristic wavelengths (510 and 460 nm). The maximum absorption at 510 nm (e = 3353 m À1 cm…”

Section: 45(4) 894(4)mentioning

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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“…35.92 32.62 À1.03 [18] pM [c] 19.3 [19] 16.0 [19] [a] Values determined in 3 % DMSO. At physiological pH, the predominant form for both compounds is the neutral species H 3 L (ca.…”

Section: 45(4) 894(4)mentioning

confidence: 99%

Section: 45(4) 894(4)mentioning

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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“…For example, gallium-labelled radiophar-0932-0776 / 04 / 0300-0291 $ 06.00 c 2004 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com maceuticals have been used for either γ scintigraphy or PET imaging in a broad range of clinical pathologies. Introduced in 1969 as a tumour imaging agent [8], 67 Ga-citrate still remains a clinically useful radiopharmaceutical [9,10]. It has been shown to detect a large variety of tumours as well as inflammation / infection sites and skeletal disorders [11,12].…”

Section: Introductionmentioning

confidence: 99%

“…It has been shown to detect a large variety of tumours as well as inflammation / infection sites and skeletal disorders [11,12]. Within the last decade there has been an intense interest in labelled monoclonal antibodies and peptides via a bifunctional metal chelating agent; this approach may lead to the development of new biospecific 67/68 Ga radiopharmaceuticals if suitable chelators are synthesized [9].…”

Section: Introductionmentioning

confidence: 99%

Preparation, Crystal Structure and Spectroscopic Characterization of [Ga(OH)(SO₄)(terpy)(H₂O)] · H₂O (terpy=2,2’:6’,2-Terpyridine): The First Characterized Gallium(III) Sulfato Complex

Sofetis

Papaefstathìou

Terzis

et al. 2004

Zeitschrift Für Naturforschung B

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In dedication to the late Professor John M. Tsangaris for his important contributions to Inorganic ChemistryThe reaction of Ga 2 (SO 4 ) 3 ·18H 2 O and excess 2,2 :6 ,2 -terpyridine (terpy) in MeOH / H 2 O leads to [Ga(OH)(SO 4 )(terpy)(H 2 O)]·H 2 O (1·H 2 O] in good yield. The structure of the complex has been determined by single-crystal X-ray crystallography. The Ga III atom in 1·H 2 O is 6-coordinate and ligation is provided by one terdentate terpy molecule, one monodentate sulfate, one terminal hydroxide and one terminal H 2 O molecule; the coodination polyhedron about the metal is described as a distorted octahedron. There is an extensive hydrogen-bonding network in the crystal structure which generates corrugated layers parallel to bc. The new complex was characterized by IR and 1 H NMR spectroscopy. The spectroscopic data are discussed in terms of the nature of bonding.

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“…Spojevi koji uspješno keliraju Fe(III) u pravilu sa sličnim afinitetom vežu i Ga(III). 8,[14][15][16] Kompleks se pripravlja miješanjem kelatora i kupovnog radioaktivno obilježenog kompleksa galijeva citrata. Potom se administrira u životinju te se one nakon određenog vremenskog razdoblja žrtvuju.…”

Section: 3unclassified

3-Hidroksipiridin-4-oni (II. dio): Biološka primjena kao kelatora željeza

et al. 2017

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N-Carboxyalkyl derivatives of 3-hydroxy-4-pyridinones: synthesis, complexation with Fe(III), Al(III) and Ga(III) and in vivo evaluation

Cited by 56 publications

References 31 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

Preparation, Crystal Structure and Spectroscopic Characterization of [Ga(OH)(SO₄)(terpy)(H₂O)] · H₂O (terpy=2,2’:6’,2-Terpyridine): The First Characterized Gallium(III) Sulfato Complex

3-Hidroksipiridin-4-oni (II. dio): Biološka primjena kao kelatora željeza

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N-Carboxyalkyl derivatives of 3-hydroxy-4-pyridinones: synthesis, complexation with Fe(III), Al(III) and Ga(III) and in vivo evaluation

Cited by 56 publications

References 31 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

Preparation, Crystal Structure and Spectroscopic Characterization of [Ga(OH)(SO4)(terpy)(H2O)] · H2O (terpy=2,2’:6’,2-Terpyridine): The First Characterized Gallium(III) Sulfato Complex

3-Hidroksipiridin-4-oni (II. dio): Biološka primjena kao kelatora željeza

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Preparation, Crystal Structure and Spectroscopic Characterization of [Ga(OH)(SO₄)(terpy)(H₂O)] · H₂O (terpy=2,2’:6’,2-Terpyridine): The First Characterized Gallium(III) Sulfato Complex