Evaluation of Novel Radioiodinated C7-substituted Δ6,7 – estradiol Derivatives for Molecular Recognition of ER-Positive Breast Tumours

Neto, Carina; Oliveira, Maria Cristina de; Gano, Lurdes; Marques, Fernanda; Santos, Isabel; Morais, Goreti Ribeiro; Yasuda, Takumi; Thiemann, Thies; Botelho, Maria Filomena; Oliveira, Carlos

doi:10.2174/1874471010902020083

Cited by 9 publications

(3 citation statements)

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“…The formation of deiodinating metabolites by CYP450 enzymes may be avoided by decreasing the lipophilicity of the whole molecule. For instance, Neto and co‐workers designed and synthesized the estradiol analogues 20a and 20b , differing in the nature of the R substituent (Figure ) . As can be seen from Table , compound 20b (bearing a nitrile in place of an amide) is deiodinated much more rapidly than 20a , with a very high residual radioactivity in the thyroid even 24 h after administration.…”

Section: Metabolic Pathways Leading To Deiodinationmentioning

confidence: 99%

Design of Radioiodinated Pharmaceuticals: Structural Features Affecting Metabolic Stability towards in Vivo Deiodination

Cavina

Born²,

Klaren

et al. 2017

Eur J Org Chem

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Radioiodinated pharmaceuticals are convenient tracers for clinical and research investigations because of the relatively long half‐lives of radioactive iodine isotopes (i.e., 123I, 124I, and 131I) and the ease of their chemical insertion. Their application in radionuclide imaging and therapy may, however, be hampered by poor in vivo stability of the C–I bond. After an overview of the use of iodine in biology and nuclear medicine, we present here a survey of the catabolic pathways for iodinated xenobiotics, including their biodistribution, accumulation, and biostability. We summarize successful rational improvements in the biostability and conclude with general guidelines for the design of stable radioiodinated pharmaceuticals. It appears to be necessary to consider the whole molecule, rather than the radioiodinated fragment alone. Iodine radionuclides are generally retained in vivo on sp2 carbon atoms in iodoarenes and iodovinyl moieties, but not in iodinated heterocycles or on sp3 carbon atoms. Iodoarene substituents also have an influence, with increased in vivo deiodination in the cases of iodophenols and iodoanilines, whereas methoxylation and difluorination improve biostability.

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Section: Metabolic Pathways Leading To Deiodinationmentioning

confidence: 99%

Design of Radioiodinated Pharmaceuticals: Structural Features Affecting Metabolic Stability towards in Vivo Deiodination

Cavina

Born²,

Klaren

et al. 2017

Eur J Org Chem

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“…The 17iodoethynyl estradiol, despite of the larger volume of the iodine relative to a proton, shows quite favourable binding, probably due to the greater polarizability of the iodine [203,204]. 17 -vinyl estradiols have also been investigated in considerable detail [205][206][207][208][209][210]. The presence of the iodovinyl group does not significantly alter the ER binding affinity [211][212][213].…”

Section: Influence Of Structural Substitutions In Estradiol On Er Binmentioning

confidence: 99%

Steroid Receptor Ligands for Breast Cancer Targeting: An Insight into Their Potential Role As Pet Imaging Agents

Oliveira¹,

Neto²,

Morais³

et al. 2012

CMC

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The design and development of radiolabelled steroid derivatives has been an important area of research due to their wellknown value in breast cancer targeting. The estrogen receptor (ER) and progesterone receptor (PR) are important biomarkers in the diagnosis, prognosis and follow-up of the therapeutic response of breast tumours. Thus, several radioligands based on estrogens and progestins have been proposed for targeted functional ER imaging. The aim of this review is to survey and analyze the developments in this field, which have led to the design of a number of PET steroid-based imaging agents, a few of which seem to be promising as radiopharmaceuticals for detection of ER-positive breast tumours.

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“…4,5 Inactive rhenium steroid composites 6,7 have been studied as model compounds for technetium analogues as all isotopes of technetium itself are radioactive. In our own search for suitable radioligands for the estrogen receptor, [8][9][10][11] we have recently examined one estrano [17,16-e]pyrimidine-tripeptide, Cys-Gly-Cys-aminopyrimidinoestrane 1 (Fig. 1), 12 where the tripeptide was to be utilised as a ligand to bind rhenium or technetium.…”

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confidence: 99%

Estrano[17,16-e]pyrimidine-amino acid and estrano[17,16-e]pyrimidine-peptide conjugates

Matsumoto

Shiine

Mataka

et al. 2009

Journal of Chemical Research

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Evaluation of Novel Radioiodinated C7-substituted Δ6,7 – estradiol Derivatives for Molecular Recognition of ER-Positive Breast Tumours

Cited by 9 publications

References 0 publications

Design of Radioiodinated Pharmaceuticals: Structural Features Affecting Metabolic Stability towards in Vivo Deiodination

Design of Radioiodinated Pharmaceuticals: Structural Features Affecting Metabolic Stability towards in Vivo Deiodination

Steroid Receptor Ligands for Breast Cancer Targeting: An Insight into Their Potential Role As Pet Imaging Agents

Estrano[17,16-e]pyrimidine-amino acid and estrano[17,16-e]pyrimidine-peptide conjugates

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