The particular role of radiopharmacy within bioorganometallic chemistry

Alberto, Roger

doi:10.1016/j.jorganchem.2006.11.019

Cited by 89 publications

(33 citation statements)

References 57 publications

(57 reference statements)

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“…For technetium, however, reactions in water are essential if one aims at using such complexes in imaging or, for rhenium, in therapy (see Introduction). [103] Until recently this constraint excluded classical organometallic ligands such as cyclopentadienyl because of incompatibility with water. Of course, text book complexes such as the piano-stool-type cymantrene analogue "cytectrene " have been known for a while but have been prepared along traditional routes.…”

Section: Basic Chemistry Of [M(oh 2 ) 3 (Co) 3 ] + In Watermentioning

confidence: 99%

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Alberto

2008

Eur J Inorg Chem

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The chemistry of technetium is essentially driven by radiopharmaceutical applications. These comprise the syntheses of novel complexes but, moreover, the combination of targeting biomolecules with metal complexes. Aqua ions are especially convenient for facilitatating the introduction of metal cations into biomolecules, but are nonexistent for Tc and Re in the Mn triad. This microreview will discuss the chemistry of those Tc complexes that contain H2O as ligands. Special attention will be payed to organometallic aqua ions, i.e. complexes that are typically organometallic with water as ligand. Of particular interest is the coordination chemistry of [M(OH2)3(CO)3]+ (M = Mn, Tc, Re) complexes in water since it is the origin of the widely applied radiopharmaceutical research with 99mTc and 188Re. The chemistry of organometallic aqua ions is not confined to Werner‐type ligands, hence, a further emphasis will be placed on pure organometallic chemistry in water.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Basic Chemistry Of [M(oh 2 ) 3 (Co) 3 ] + In Watermentioning

confidence: 99%

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Alberto

2008

Eur J Inorg Chem

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“…Following the initial appearance of this term in 1985, 1 this field gradually became a hotbed of research into new applications of organometallics, particularly in therapy and diagnostics. [2][3][4][5][6][7][8][9][10][11][12] We have shown that some ferrocene derivatives are very active against cancer cells. The addition of a ferrocenyl moiety to selected polyaromatic phenols, [13][14][15][16] amines, 17,18 amides, 19 and esters 19,20 can potentiate their antiproliferative effects against breast and prostate cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Metabolism of Ferrocene Analogues of Tamoxifen: Characterization and Antiproliferative Activities of the Metabolites

et al. 2015

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Keywords: breast cancer, ferrocifen, indene metabolites, P450-dependent oxidation, quinone methides Ferrociphenols have been found to have high antiproliferative activity against estrogenindependent breast cancer cells. The rat and human liver microsome-mediated metabolism of three compounds of the ferrocifen (FC) family, 1,1-bis(4-hydroxy-phenyl)-2-ferrocenylbut-1-ene (FC1), 1-(4-hydroxyphenyl)-1-(phenyl)-2-ferrocenyl-but-1-ene (FC2), and 1-[4-(3-dimethylaminopropoxy)phenyl]-1-(4-hydroxyphenyl)-2-ferrocenyl-but-1-ene (FC3), was studied.Three main metabolite classes were identified: quinone methides (QMs) deriving from twoelectron oxidation of FCs, cyclic indene products (CPs) deriving from acid-catalyzed cyclization of QMs, and allylic alcohols (AAs) deriving from hydroxylation of FCs. These metabolites are generated by cytochromes P450 (P450s), as shown by experiments with either N-benzylimidazole as a P450 inhibitor or recombinant human P450s. Such P450-dependent oxidation of the phenol function and hydroxylation of the allylic CH 2 group of FCs leads to the formation of QM and AA metabolites, respectively. Some of the new ferrociphenols obtained in this study were found to exhibit remarkable antiproliferative effects toward MDA-MB-231 hormone-independent breast cancer cells.

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“…In recent years, technetium and rhenium complexes in low oxidation states have attracted significant attention 30-32. In particular, the fac -{M I (CO) 3 } + core (M = Re, 99m Tc) has been assessed because of its small size, its low-spin d6 electronic configuration, and the high chemical and kinetic stability of its complexes 30.…”

Section: Introductionmentioning

confidence: 99%

Coordination Modes of Multidentate Ligands infac-[Re(CO)₃(polyaminocarboxylate)] Analogues of^99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions

Lipowska¹,

He²,

Xu³

et al. 2010

Inorg. Chem.

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We study Re analogues of 99mTc renal agents to interpret previous results at the 99mTc tracer level. The relative propensities of amine donors vs. carboxylate oxygen donors of four L = polyaminocarboxylate ligands to coordinate in fac-[ReI(CO)3L]n complexes were assessed by examining the reaction of fac-[ReI(CO)3(H2O)3]+ under conditions differing in acidity and temperature. All four L [N,N-bis-(2-aminoethyl)glycine (DTGH), N,N-ethylenediaminediacetic acid, diethylenetriamine-N-malonic acid, and diethylenetriamine-N-acetic acid] can coordinate as tridentate ligands while creating a dangling chain terminated in a carboxyl group. Dangling carboxyl groups facilitate renal clearance in fac-[99mTcI(CO)3L]n agents. Under neutral conditions, the four ligands each gave two fac-[ReI(CO)3L]n products with HPLC traces correlating well with known traces of the fac-[99mTcI(CO)3L]n mixtures. Such mixtures are common in renal agents because the needed dangling carboxyl group can compete for a coordination site. However, the HPLC separations needed to assess the biodistribution of a single tracer are impractical in a clinical setting. One goal in investigating this Re chemistry is to identify conditions for avoiding this problem of mixtures in preparations of fac-[99mTcI(CO)3L]n renal tracers. After separation and isolation of the fac-[ReI(CO)3L]n products, NMR analysis of all products and single crystal X-ray crystallographic analysis of both DTGH products as well as one product each from the other L allowed us to establish coordination mode unambiguously. The product favored in acidic conditions has a dangling amine chain and more bound oxygen. The product favored in basic conditions has a dangling carboxyl chain and more bound nitrogen. At the elevated temperatures used for simulating tracer preparation, equilibration was facile (ca. one hour or less), allowing selective formation of one product by utilizing acidic or basic conditions. The results of this fundamental study offer protocols and guidance useful for the design and preparation of fac-[99mTcI(CO)3L]n agents consisting of a single tracer.

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The particular role of radiopharmacy within bioorganometallic chemistry

Cited by 89 publications

References 57 publications

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Oxidative Metabolism of Ferrocene Analogues of Tamoxifen: Characterization and Antiproliferative Activities of the Metabolites

Coordination Modes of Multidentate Ligands infac-[Re(CO)₃(polyaminocarboxylate)] Analogues of^99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions

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The particular role of radiopharmacy within bioorganometallic chemistry

Cited by 89 publications

References 57 publications

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Oxidative Metabolism of Ferrocene Analogues of Tamoxifen: Characterization and Antiproliferative Activities of the Metabolites

Coordination Modes of Multidentate Ligands infac-[Re(CO)3(polyaminocarboxylate)] Analogues of99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions

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Coordination Modes of Multidentate Ligands infac-[Re(CO)₃(polyaminocarboxylate)] Analogues of^99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions