Novel analogs of antitumor agent calixarene 0118: Synthesis, cytotoxicity, click labeling with 2-[18F]fluoroethylazide, and in vivo evaluation

Läppchen, Tilman; Dings, Ruud P.M.; Rossin, Raffaella; Simon, Justine; Visser, T.; Bakker, Martine; Walhe, Priya; Mourik, Tiemen van; Donato, Katia; Beijnum, Judy R. van; Lub, Johan; Robillard, Marc S.; Mayo, Kevin H.; Grüll, Holger

doi:10.1016/j.ejmech.2014.10.048

Cited by 42 publications

(30 citation statements)

References 45 publications

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“…Furthermore, plant pectins and galactomannans have also shown antitumoral activities by virtue of their ability to bind galectins [154,155]; yet recent studies demonstrated that these naturally-occurring saccharides exhibit low inhibitory potency towards galectins CRDs [156]. Peptidebased galectin inhibitors such as anginex [77,157] or its derivatives 6DBF7 [158] or OTX008 [159,160] have also been shown to inhibit galectin functions including tumor angiogenesis and cell migration. Further studies should be aimed at evaluating this portfolio of anti-galectin compounds in pre-clinical settings and clinically-relevant tumor models.…”

Section: Discussionmentioning

confidence: 99%

Galectins: Multitask signaling molecules linking fibroblast, endothelial and immune cell programs in the tumor microenvironment

Elola

Ferragut

Méndez-Huergo

et al. 2018

Cellular Immunology

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Section: Discussionmentioning

confidence: 99%

Galectins: Multitask signaling molecules linking fibroblast, endothelial and immune cell programs in the tumor microenvironment

Elola

Ferragut

Méndez-Huergo

et al. 2018

Cellular Immunology

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“…171,173 The MeCN from co-distillation or trapping led in some cases to a decrease in coupling efficiency. 178 For the prostate-specific membrane antigen (PSMA) tracers 222 and 223, higher MeCN content led to a decrease in yield from 50% to o25% (measured by radio-HPLC). 161 However, a few successful click reactions were also performed in MeCN.…”

Section: Fluorine-18 Labelled Azidesmentioning

confidence: 99%

Fluorine-18 labelled building blocks for PET tracer synthesis

et al. 2017

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Positron emission tomography (PET) is an important driver for present day healthcare. Fluorine-18 is the most widely used radioisotope for PET imaging and a thorough overview of the available radiochemistry methodology is a prerequisite for selection of a synthetic approach for new fluorine-18 labelled PET tracers. These PET tracers can be synthesised either by late-stage radiofluorination, introducing fluorine-18 in the last step of the synthesis, or by a building block approach (also called modular build-up approach), introducing fluorine-18 in a fast and efficient manner in a building block, which is reacted further in one or multiple reaction steps to form the PET tracer. This review presents a comprehensive overview of the synthesis and application of fluorine-18 labelled building blocks since 2010.

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“…Calix [4]arene 0118 (Scheme 4) is a proven potent antiangiogenic agent that effectively inhibits tumor growth in preclinical studies and is presently under investigation in a phase-I clinical trials. [70][71][72] Recently, Lappchen et al [73] synthesized close mimetics of calixarene 0118 of the types 8 and 9 (Scheme 4) and evaluated their cytotoxic properties. All the newly synthesized analogs were not only proved to be equipotent to calixarene 0118, but some of them also inhibited human umbilical vein endothelial cells (HUVEC) and MA148 ovarian carcinoma cell growth nearly 4-and 10-fold more effectively, which is a straightforward evidence of the potential of this class of compounds in anti-angiogenic…”

Section: Lower-rim-functionalized Calix[4] Arenesmentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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Novel analogs of antitumor agent calixarene 0118: Synthesis, cytotoxicity, click labeling with 2-[18F]fluoroethylazide, and in vivo evaluation

Cited by 42 publications

References 45 publications

Galectins: Multitask signaling molecules linking fibroblast, endothelial and immune cell programs in the tumor microenvironment

Galectins: Multitask signaling molecules linking fibroblast, endothelial and immune cell programs in the tumor microenvironment

Fluorine-18 labelled building blocks for PET tracer synthesis

Functionalized calix[4]arenes as potential therapeutic agents

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