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  • Novel derivatives of 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with improved fluorescent and σ receptors binding properties.

Novel derivatives of 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with improved fluorescent and σ receptors binding properties.

Journal of medicinal chemistry (2014-04-05)
Carmen Abate, Mauro Niso, Roberta Marottoli, Chiara Riganti, Dario Ghigo, Savina Ferorelli, Giulia Ossato, Roberto Perrone, Enza Lacivita, Don C Lamb, Francesco Berardi
ABSTRACT

Despite the promising potentials of σ2 receptors in cancer therapy and diagnosis, there are still ambiguities related to the nature and physiological role of the σ2 protein. With the aim of providing potent and reliable tools to be used in σ2 receptor research, we developed a novel series of fluorescent σ2 ligands on the basis of our previous work, where high-affinity σ2 ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazine (1, PB28) was used as the pharmacophore. Compared to the previous compounds, these novel ligands displayed improved fluorescence and σ2 binding properties, were σ2-specifically taken up by breast tumor cells, and were successfully employed in confocal microscopy. Compound 14, which was the best compromise between pharmacological and fluorescent properties, was successfully employed in flow cytometry, demonstrating its potential to be used as a tool in nonradioactive binding assays for studying the affinity of putative σ2 receptor ligands.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
四氢呋喃, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
Sigma-Aldrich
活性炭负载钯催化剂, 10% Pd basis
Sigma-Aldrich
溴代环丙烷, 99%
Sigma-Aldrich
碳负载钯催化剂, sulfided, extent of labeling: 5 wt. % loading (dry basis), matrix activated carbon, wet support, (wet)