N-(N-Benzylpiperidin-4-yl)-2-[18F]fluorobenzamide: A potential ligand for PET imaging of σ receptors

Shiue, Chyng‐Yann; Shiue, Grace G.; Zhang, Sue X.; Wilder, Susan Z.; Greenberg, Joel; Bénard, François; Wortman, Jeffrey A.; Alavi, Abass

doi:10.1016/s0969-8051(97)00097-8

Cited by 32 publications

(15 citation statements)

References 29 publications

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“…In addition, even fewer studies were made on 3 ligands [46], probably because subtype 3 warrants further investigation. Many specific radioligands for 1 receptor subtypes were synthesized [28][29][30]40,[47][48][49][50][51], but none for 2 or 3 receptor subtypes. [ 3 H]-(+)-Pentazocine is the most commonly used radiolabel for 1 sites, while [ 3 H]-DTG in the presence of (+)-pentazocine for 2 sites.…”

Section: Introductionmentioning

confidence: 99%

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

Gund

Floyd

Jung

2004

Journal of Molecular Graphics and Modelling

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Section: Introductionmentioning

confidence: 99%

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

Gund

Floyd

Jung

2004

Journal of Molecular Graphics and Modelling

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“…These are spipethiane 24 molecules shown in Table 1, piperidine and piperazine analogs 25 shown in Table 2, and benzoxazolone and benzothiazolone compounds 26 shown in Table 3. The remaining compounds [27][28][29] are shown in Table 4. Test compounds were labeled in these tables.…”

Section: Selection Of Ligandsmentioning

confidence: 99%

A comparative molecular field analysis (CoMFA) study using semiempirical, density functional, ab initio methods and pharmacophore derivation using DISCOtech on sigma 1 ligands

2004

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Abstract:The Comparative Molecular Field Analysis (CoMFA) was developed to investigate a threedimensional quantitative structure activity relationship (3D-QSAR) model of ligands for the sigma 1 receptor. The starting geometry of sigma-1 receptor ligands was obtained from the Tripos force field minimizations and conformations were decided from DISCOtech using the SYBYL 6.8. program. The structures of 48 molecules were fully optimized at the ab initio HF/3-21G* and semiempirical AM1 calculations using GAUSSIAN 98. The electrostatic charges were calculated using several methods such as semiempirical AM1, density functional B3LYP/3-21G*, and ab initio HF/3-21G*, MP2/3-21G* calculations within GAUSSIAN 98. Using the optimized geometries, the CoMFA results derived from the HF/3-21G method were better than those from AM1. The best CoMFA was obtained from HF/3-21G* optimized geometry and charges (R 2 ϭ 0.977). Using the optimized geometries, the CoMFA results derived from the HF/3-21G methods were better than those from AM1 calculations. The training set of 43 molecules gave higher R 2 (0.989 -0.977) from HF/3-21G* optimized geometries than R 2 (0.966 -0.911) values from AM1 optimized geometries. The test set of five molecules also suggested that HF/3-21G* optimized geometries produced good CoMFA models to predict bioactivity of sigma 1 receptor ligands but AM1 optimized geometries failed to predict reasonable bioactivity of sigma 1 receptor ligands using different calculations for atomic charges.

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“…14 There are reports of the imaging of sigma receptors present in the brain and in other tumor cells, using both positron emission tomography (PET) and single-photon emission tomography (SPET). In this respect, various 11 C-and 18 F-labeled, 15,16 as well as 99m Tc-labeled 17,18 and radioiodinated 19 receptor ligands, have been reported to be selective for sigma-receptor sites. These ligands have been employed for the imaging of different kinds of tumors (e.g., human melanoma, non-small-cell lung carcinoma, breast carcinoma, and metastatic melanoma).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ^99mTc-Nitrido Heterocomplex of Piperidine and In Vitro and In Vivo Evaluation of Its Affinity for Sigma Receptors

Satpati

Bapat²,

Sarma³

et al. 2008

Cancer Biotherapy and Radiopharmaceuticals

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Sigma receptors are overexpressed in various types of cancer cells, making ligands that bind to these receptors attractive vectors for targeting radiation to specific sites for the imaging and therapy of oncologic disorders. In this paper, we report the synthesis of a dithiocarbamate derivative of 4-amino-N-benzylpiperidine and its radiolabeling with the [(99m)TcN(PNP)](2+) metal synthon. The radiolabeled tracer has been evaluated for sigma-receptor specificity. The radiochemical purity of the (99m)Tc-complex was >98%. The in vitro cell-binding and competition studies of the complex showed affinity and specificity toward fibrosarcoma and melanoma cells. In vivo studies carried out in mice bearing melanoma and fibrosarcoma tumors showed tumor uptakes of 1% and 1.9%, respectively, at 3 hours postinjection. In vivo blocking studies were carried out, using (+)-pentazocine, a sigma-receptor-specific agent where approximately 40% decrease in the tumor uptake was observed. The affinity of [(99m)TcN(PNP)Pip-DTC](+) complex for sigma-receptor sites ascertained through in vitro and in vivo studies makes it a potential agent for further investigation.

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N-(N-Benzylpiperidin-4-yl)-2-[18F]fluorobenzamide: A potential ligand for PET imaging of σ receptors

Cited by 32 publications

References 29 publications

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

A comparative molecular field analysis (CoMFA) study using semiempirical, density functional, ab initio methods and pharmacophore derivation using DISCOtech on sigma 1 ligands

Synthesis of ^99mTc-Nitrido Heterocomplex of Piperidine and In Vitro and In Vivo Evaluation of Its Affinity for Sigma Receptors

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N-(N-Benzylpiperidin-4-yl)-2-[18F]fluorobenzamide: A potential ligand for PET imaging of σ receptors

Cited by 32 publications

References 29 publications

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

Molecular modeling of σ1 receptor ligands: a model of binding conformational and electrostatic considerations

A comparative molecular field analysis (CoMFA) study using semiempirical, density functional, ab initio methods and pharmacophore derivation using DISCOtech on sigma 1 ligands

Synthesis of 99mTc-Nitrido Heterocomplex of Piperidine and In Vitro and In Vivo Evaluation of Its Affinity for Sigma Receptors

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Synthesis of ^99mTc-Nitrido Heterocomplex of Piperidine and In Vitro and In Vivo Evaluation of Its Affinity for Sigma Receptors