Synthesis and characterization of rhenium and technetium-99m tricarbonyl complexes bearing the 4-[3-bromophenyl]quinazoline moiety as a biomarker for EGFR-TK imaging

Bourkoula, Athanasia; Paravatou-Petsotas, Maria; Papadopoulos, Apostolos N.; Santos, Isabel; Pietzsch, Hans‐Jürgen; Livaniou, Evangelia; Pelecanou, Maria; Papadopoulos, Minas; Pirmettis, Ioannis

doi:10.1016/j.ejmech.2009.04.033

Cited by 44 publications

(34 citation statements)

References 33 publications

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“…47 Based on the promising results of the tricarbonyl compounds 32 and 36, another compound, 34, and its rhenium analog, were synthesized in an attempt to improve upon the inhibition properties of these technetium-complexed quinazoline imaging agents. 48 Like the previous compounds, 34 was able to cross the membrane of A431 cells and its inhibition of both phosphorylation and cell growth proved to be better than 32. Additionally, 34 had a more favorable profile than the "4+1" 99m Tc mixed-ligand complex 39 and was comparable to that of 40.…”

Section: Small Molecule Inhibitors Labeled With Radiometalsmentioning

confidence: 83%

Imaging EGFR and HER2 by PET and SPECT: A Review

Corcoran

Hanson

2013

Medicinal Research Reviews

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In an effort to discover a noninvasive method for predicting which cancer patients will benefit from therapy targeting the EGFR and HER2 proteins, a large body of the research has been conducted toward the development of PET and SPECT imaging agents, which selectively target these receptors. We provide a general overview of the advances made toward imaging EGFR and HER2, detailing the investigation of PET and SPECT imaging agents ranging in size from small molecules to monoclonal antibodies.

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Section: Small Molecule Inhibitors Labeled With Radiometalsmentioning

confidence: 83%

Imaging EGFR and HER2 by PET and SPECT: A Review

Corcoran

Hanson

2013

Medicinal Research Reviews

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“…hergestellt 14. Für die Synthese von L 1 wurde eine literaturbekannte Methode modifiziert15 und A mit einem Überschuss Pyridin‐2‐carboxaldehyd in siedendem Methanol in 94 % Ausbeute umgesetzt. L 2 wurde durch direkte reduktive Aminierung von N ‐Boc‐2‐aminoacetaldehyd und A mit Natriumcyanoborhydrid unter schwach sauren Bedingungen und anschließendem Entschützen mit Salzsäure in einer Gesamtausbeute von 70 % synthetisiert.…”

Section: Methodsunclassified

Tumorspezifische, Hypoxie‐basierte Aktivierung von EGFR‐Inhibitoren

et al. 2014

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Die Entwicklung von Rezeptor-Tyrosinkinase-Inhibitoren (TKIs) ist ein Meilenstein in der Entwicklung neuer Tumortherapeutika. Allerdings geht die TKI-Therapie mit starken Nebenwirkungen und Chemotherapieresistenz einher. Ziel dieser Studie war die Synthese und präklinische Entwicklung eines neuen Inhibitors des Epidermalen Wachstumsfaktorrezeptors (EGFR), der durch die spezifischen Eigenschaften des malignen Gewebes aktiviert wird. Zu diesem Zweck wurde ein Co III -basiertes "Prodrug-Design" verwendet, das die gezielte Freisetzung des aktiven EGFR-Inhibitors durch den im soliden Tumor auftretenden Sauerstoffmangel (Hypoxie) ermçglicht. Hierfür wurden mehrere neue EGFRhemmende Liganden mit Chelateinheiten synthetisiert, und derjenige mit dem grçßten EGFR-hemmenden Potenzial wurde für die Komplexierung mit Co III ausgewählt. Anschließend wurden hypoxische Aktivierung und Hemmung des EGFR-Signalwegs nachgewiesen, und eine vielversprechende Aktivität des neuen Komplexes in vivo wurde gezeigt.

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“…The combi-targeting approach consists of synthesizing agents termed "combi-molecules" that are not only capable of inhibiting EGFR-mediated signaling on their own but also to be hydrolyzed under physiological conditions to release another EGFR TK inhibitor + a cytotoxic DNA-alkylating species [32][33][34]. cSrc/Abl kinase inhibitors are also enumerated in the "C" [35][36][37] and the templates of "D" [38] are designed for HDAC/EGFR/HER2 inhibitors; "E" [23] represents the design of DNA intercalating agents and "F" [39] has a special use as a biomarker for EGFR-TK imaging.…”

Section: "6 7-tails"mentioning

confidence: 99%

Exploration of Chemical Space Based on 4-Anilinoquinazoline

Li¹,

Hou²,

Wang³

et al. 2012

CMC

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Chemical space is defined as all possible small organic molecules, including those present in biological systems, which is so vast that so far only a tiny fraction of it has been explored. Indeed, a thorough examination of all "chemical space" is practically impossible. The success of three EGFR inhibitors (Gefitnib, Erlotinib, Lapatinib) suggests that 4-anilinoquinazoline scaffold is still worth developing in the future. To date hundreds of this sort of derivatives have been synthesized and show potent anticancer activities. Most of the compounds have been proved to be EGFR/HER2 kinase inhibitors, binding at the hinge region of the ATP site and some lead compounds have been optimized against a number of different kinases, including VEGFR-2, Src, Aurora A/B, Tpl, Clk and PDE10A. Now there is now a rich pipeline of novel anticancer agents based on 4-anilinoquinazoline in early phase clinical trials. This review will highlight the exploration of chemical space of 4-anilinoquinazoline in the past ten years and we hope that increasing knowledge of the SAR and cellular processes underlying the antitumor-activity of anilinoquinazoline derivatives will be beneficial to the rational design of new generation of small molecule anticancer drugs.

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Synthesis and characterization of rhenium and technetium-99m tricarbonyl complexes bearing the 4-[3-bromophenyl]quinazoline moiety as a biomarker for EGFR-TK imaging

Cited by 44 publications

References 33 publications

Imaging EGFR and HER2 by PET and SPECT: A Review

Imaging EGFR and HER2 by PET and SPECT: A Review

Tumorspezifische, Hypoxie‐basierte Aktivierung von EGFR‐Inhibitoren

Exploration of Chemical Space Based on 4-Anilinoquinazoline

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