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Synthesis and screening of mono- and di-aryl technetium and rhenium metallocarboranes. A new class of probes for the estrogen receptor.

Synthesis and screening of mono- and di-aryl technetium and rhenium metallocarboranes. A new class of probes for the estrogen receptor.

Journal of medicinal chemistry (2008-04-17)

Patrick W Causey, Travis R Besanger, John F Valliant

ABSTRACT

A series of mono and diaryl rhenium(I)-carborane derivatives were prepared using microwave heating and screened for their affinity for two isoforms of the estrogen receptor (ER). The rhenacarborane derivative [(RR'C 2B9H9)Re(CO)3](-) (R = p-PhOH, R' = H), which was generated by taking advantage of a recently discovered cage isomerization process, and the neutral nitrosated analogue [(RR'C2B9H9)Re(CO)2(NO)] (R = p-PhOH, R' = H) showed the highest affinities of the compounds screened. As a result, the (99m)Tc analogue of one of the leads was produced in high yield (84%) and specific activity in a manner that is suitable for routine production in support of future preclinical and molecular imaging studies.

MATERIALS

Product Number

Brand

Product Description

Supelco

p-Cresol, analytical standard

Sigma-Aldrich

o-Cresol, ≥99%

Supelco

Pentachlorophenol solution, certified reference material, 5000 μg/mL in methanol

Sigma-Aldrich

p-Cresol, ≥99%, FG

Sigma-Aldrich

Pentachlorophenol, 97%

Sigma-Aldrich

4-Phenylphenol, 97%

Sigma-Aldrich

4-Chlorophenol, ≥99%

Sigma-Aldrich

4-Phenylphenol, purified by sublimation, 99%

Sigma-Aldrich

β-Estradiol, powder, γ-irradiated, suitable for cell culture

Sigma-Aldrich

β-Estradiol, BioReagent, powder, suitable for cell culture

Supelco

o-Cresol, analytical standard

Sigma-Aldrich

β-Estradiol, analytical standard

Sigma-Aldrich

o-Cresol, ReagentPlus^®, ≥99%

Sigma-Aldrich

p-Cresol, 99%

Sigma-Aldrich

Phenol, BioUltra, for molecular biology, ≥99.5% (GC)

Sigma-Aldrich

Phenol, unstabilized, purified by redistillation, ≥99%

Sigma-Aldrich

2,4,6-Trichlorophenol, 98%

Sigma-Aldrich

Phenol, contains hypophosphorous as stabilizer, loose crystals, ACS reagent, ≥99.0%

Sigma-Aldrich

Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, ≥99.5% (GC), crystalline (detached)

Sigma-Aldrich

Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (GC)

Sigma-Aldrich

Phenol, BioUltra, for molecular biology, TE-saturated, ~73% (T)

Sigma-Aldrich

Diphenyl ether, ReagentPlus^®, ≥99%

Sigma-Aldrich

Diphenyl ether, ReagentPlus^®, 99%

Sigma-Aldrich

Diphenyl ether, ≥99%, FG

Sigma-Aldrich

Phenol, puriss. p.a., ACS reagent, reag. Ph. Eur., 99.0-100.5%

Supelco

Phenol solution, 100 μg/mL in acetonitrile, PESTANAL^®, analytical standard

Sigma-Aldrich

Estradiol, meets USP testing specifications

Sigma-Aldrich

Phenol, BioXtra, ≥99.5% (GC)

Sigma-Aldrich

Phenol solution, Equilibrated with 10 mM Tris HCl, pH 8.0, 1 mM EDTA, BioReagent, for molecular biology

Sigma-Aldrich

Phenol solution, BioReagent, Saturated with 0.01 M citrate buffer, pH 4.3 ± 0.2, for molecular biology