Synthesis of new ligands for targeting the S1P1 receptor

Schilson, Stefanie S.; Keul, Petra; Shaikh, Rizwan S.; Schäfers, Michael; Levkau, Bodo; Haufe, Günter

doi:10.1016/j.bmc.2015.01.014

Cited by 17 publications

(10 citation statements)

References 39 publications

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“…In view of the important role of S1PR1 in the occurrence, development and metastasis of tumors, noninvasive monitoring of the expression of S1PR1 in malignant tumors has important clinical significance in formulating tumor treatment plans, monitoring treatment effects, and evaluating prognosis. In some recent studies, Tu's and Haufe's groups have designed and synthesized a series of S1PRs, including specific carbon-11and fluorine-18-labeled radiotracers highly targeted to S1PR1 (16)(17)(18)(19)(20)(21). They have shown promising cell membrane binding assays in vitro towards S1PRs.…”

Section: Introductionmentioning

confidence: 99%

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

Gai

et al. 2021

Front. Immunol.

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Sphingosine-1-phosphate (S1P) is a phospholipid that regulates pleiotropic biological activities and exerts extracellular functions by binding to five specific G-protein-coupled receptors, S1P receptors (S1PR) 1–5. When activated by S1P, S1PR promote the proliferation and invasion of tumor cells by inducing the formation of new blood vessels. We developed and assessed a new monoclonal antibody imaging probe 99mTc-HYNIC-S1PR1mAb, to explore the feasibility of targeting the S1PR1 in vitro and in vivo. S1PR1mAb was prepared and followed by technetium-99m labeling with succinimidyl 6-hydraziniumnicotinate hydrochloride. Cell uptake and blocking studies were performed to investigate the binding specificity of 99mTc-HYNIC-S1PR1mAb in vitro. 99mTc-HYNIC-S1P1mAb was also tested in vivo in mice xenografted with SK-HEP-1 (high-expression of S1PR1) and MCF-7 (low-expression of S1PR1) using single-photon emission-computed tomography (SPECT). Ex vivo gamma counting of tissues from tumor-bearing mice was used to evaluate 99mTc-HYNIC-S1PR1mAb biodistribution. The biodistribution study results showed significantly higher uptake in SK-HEP-1 tumors than in MCF-7 tumors (P < 0.001). Reduced uptake of 99mTc-HYNIC-S1PR1mAb in SK-HEP-1 was observed in tumor-bearing nude mice pretreated with fingolimod, which binds competitively to the receptors, especially S1PR1. 99mTc-HYNIC-S1PR1mAb can be synthesized and specifically targeted to S1PR1 in vitro and in vivo, allowing S1PR1 expression assessment with SPECT imaging.

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Section: Introductionmentioning

confidence: 99%

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

Gai

et al. 2021

Front. Immunol.

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“…Furthermore, Haufe et al synthesized amino acid derivatives with monofluorovinylic side chain. 30 The first step involved oxidation of the starting material by SeO2 (Scheme 18). Further condensation of the generated fluorinated alcohol 90 with N-Boc-glycine allowed the formation of the amino ester enolate.…”

Section: Scheme 16 Synthesis Of Fluoroallyl Amino Acid By Alkylation Of Iminementioning

confidence: 99%

Amino acids with fluorinated olefinic motifs – synthetic approaches

Salamon-Krokosz¹,

Koroniak-Szejn²,

Koroniak³

2020

Arkivoc

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Peptidomimetics are molecules related to natural peptides that have an artificial unit incorporated in their structure. Such structural modifications, mimicking properties of natural amino acids, can be responsible for differently pronounced activity. Among others, amino acid derivatives with fluorinated olefinic motifies can act as building blocks in the synthesis of complex molecules with potential biological activity. Therefore, the synthetic approaches to the fluorinated olefinic moiety amino acids are of interest to organic chemists. There are different synthetic methods yielding fluorinated olefins having significant value in the synthesis of amino acid derivatives. This mini review describes the latest achievements in the synthesis of amino acids bearing mono-, di-or trifluorovinyl moiety.

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“…The Haufe group also examined a Claisen rearrangement to give monofluoroalkenes during the synthesis of some new ligands targeting the S1P 1 receptor. 157 Esterification with Boc-Glu of an allylic fluorinated alcohol gave the amino ester that underwent a chelate ester enolate Claisen rearrangement to afford the corresponding (Z)-monofluoroalkene (Scheme 149). Interestingly, complete chirality transfer was observed.…”

Section: Scheme 147 Eschenmoser-claisen-type Rearrangement Of 2-fluormentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Synthesis of new ligands for targeting the S1P1 receptor

Cited by 17 publications

References 39 publications

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

A Novel Radioimmune 99mTc-Labeled Tracer for Imaging Sphingosine 1-Phosphate Receptor 1 in Tumor Xenografts: An In Vitro and In Vivo Study

Amino acids with fluorinated olefinic motifs – synthetic approaches

Synthesis of Monofluoroalkenes: A Leap Forward

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