Journal of Labelled Compounds and Radiopharmaceuticals

Yao, Fen‐Mei; Palmer, Sonya L.; Khanolkar, Atmaram D.; Tian, Xiaoyu; Guo, Jianxin; Makriyannis, Alexandros

doi: 10.1002/jlcr.650pmid: N/A

Four isotopically labeled, metabolically stable analogs of arachidony‐lethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five‐step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studying the conformational properties of anandamide in model membrane systems using solid‐state NMR spectroscopy. The synthetic methods described can be applied to the preparations of other anandamide analogs with isotopic labeling in different positions of the molecule, which could be utilized in biochemical and pharmacological experiments. Copyright © 2002 John Wiley & Sons, Ltd.

Gawell, Lars

doi: 10.1002/jlcr.651pmid: N/A

The synthesis of carbon‐14 labelled N,N‐diethyl‐4‐(phenyl‐(piperidin‐4‐ylidene)methyl)‐benzamide is described. The radioisotope is introduced via an aryllithium reaction with 14CO2 to form the labelled acid, which is subsequently transformed into the amide. Copyright © 2002 John Wiley & Sons, Ltd.

Dischino, Douglas D.; Gribkoff, Valentin K.; Hewawasam, Piyasena; Luke, George M.; Rinehart, J. Kent; Spears, Tony L.; Starrett, John E.

doi: 10.1002/jlcr.652pmid: N/A

The syntheses of tritium labeled (S)‐3‐(5‐chloro‐2‐(OC3H3)methoxyphenyl‐1,3‐dihydro‐3‐fluoro‐6‐(trifluoromethyl)‐1H‐indol‐2‐one, and carbon‐14 (S)‐3‐(5‐chloro‐2‐methoxyphenyl)‐1,3‐dihydro‐3‐fluoro‐6‐(trifluoromethyl)‐2H‐(2,3‐14C2) indol‐2‐one are reported. The 3H‐labeled compound was prepared in a two‐step synthesis from C3H3I. The final product was purified via chiral HPLC to yield the desired enantiomer in a 4% radiochemical yield and a specific activity of 60 Ci/mmol. The 14C‐labeled compound was prepared in a four‐step synthesis from diethyl (carboxylate‐14C1,2) oxalate. The final product was purified via chiral HPLC to yield the desired enantiomer in a 20% radiochemical yield and a specific activity of 28.4 μCi/mg. Copyright © 2002 John Wiley & Sons, Ltd.

Hernandez, L.; Casanova, E.; Loupy, A.; Petit, A.

doi: 10.1002/jlcr.653pmid: N/A

A rapid and novel one‐pot radiochemical synthesis of 14C‐labelled esters has been developed using a combination of solvent‐free conditions and microwave irradiation. The method offers several advantages over the customary classical procedure. Copyright © 2002 John Wiley & Sons, Ltd.

Dischino, Douglas D.; Lee, Che‐Wah; Belema, Makonen; Zusi, Christopher

doi: 10.1002/jlcr.654pmid: N/A

Carbon‐14 labeled (R)‐3‐fluoro‐4‐(2′‐(5′′, 6′′, 7′′, 8′′‐tetrahydro‐5′′, 5′′, 8′′, 8′′‐tetramethyl‐2′′‐naphthyl)‐(2′‐hydroxy‐14C))(carbonyl‐14C)acetamidobenzoic acid, 1, was prepared in a six step radioactive synthesis from diethyl (carboxylate‐14C1,2) oxalate. The penultimate compound was purified by chiral HPLC, which following deprotection yielded 1 in an overall radiochemical yield of 6.8%. The specific activity of the final product was found to be 24.5 µCi/mg with a radiochemical purity of > 99% as determined by HPLC. Derivatization of 1 via trimethylsilyl diazomethane to the corresponding methyl ester 9, followed by chiral HPLC analysis, demonstrated that 1 had an optical purity of > 99% ee. Copyright © 2002 John Wiley & Sons, Ltd.

Dischino, Douglas D.; Banville, Jacques; Remillard, Roger

doi: 10.1002/jlcr.655pmid: N/A

Carbon‐14 labeled 4‐(4‐(2‐(2‐(bis(4‐chlorophenyl)methoxyethylsulfonyl) (1‐14C)ethoxy)phenyl)‐1,1,1‐trifluoro‐2‐butanone was prepared in a six step radioactive synthesis from 2‐bromo(1‐14C)acetic acid. The overall radiochemical yield was 2.2%. The specific activity of the final product was found to be 42μCi/mg with a radiochemical purity of >98%. Copyright © 2002 John Wiley & Sons, Ltd.

Wagner, S.; Eritja, R.; Zuhayra, M.; Oberdorfer, F.; Mohammed, A.; Mier, W.; Haberkorn, U.; Eisenhut, M.

doi: 10.1002/jlcr.656pmid: N/A

A solid phase technique for the preparation of antisense oligodeoxynucleotides (ODNs) is described featuring 5′‐end conjugated 4‐((1,4,8,11‐tetraazacyclotet‐radec‐1‐yl)‐methyl)benzoic acid (CPTA). Using Fmoc‐protected CPTA–C6 amidite, CPTA was conjugated to ODNs at the end of an automated DNA synthesis. To illustrate successful conjugations, the CPTA–ODNs were labeled with 99mTc using the stannous‐chloride reduction method. The resulting 99mTc complexes showed differences of stability between CPTA‐conjugated and CPTA‐unconjugated as well as 3′‐protected and 3′‐unprotected ODNs. Propane‐1,3‐diol 3′‐modification enhanced efficiently the stability of 99mTc labeled ODN against exonuclease degradation. Fmoc3CPTA‐C6 amidite turned out to be a versatile ligand for radiometal complexation at the 5′‐end. Copyright © 2002 John Wiley & Sons, Ltd.

Shevchenko, V.P.; Nagaev, I.Yu.; Myasoedov, N.F.; Yudushkin, I.A.; Gretskaya, N.M.; Bobrov, M.Yu.; Bezuglov, V.V.

doi: 10.1002/jlcr.663pmid: N/A

Tritium labelled arachidonic acid amides with dopamine, serotonin, vanillyl‐amine and the ethyleneglycol ester moieties with high specific activity (120 Ci/mmol) and yield (70–90%) were prepared from tritiated arachidonic acid by condensation with the corresponding amines and alcohol via mixed anhydrides or acyl fluorides. The labelled compounds were used for studying their uptake by mouse spleen lymphocytes. From the data obtained it was suggested that arachidonic acid amides permeate the membrane by means of passive diffusion, while transmembrane transport of arachidonoylethyleneglycol seems to be driven by the concentration gradient, maintained by hydrolytic enzymes. The compounds synthesized by the reported methods can also be used in receptor binding studies and in the oxidative metabolism of fatty acids amides and esters. Copyright © 2002 John Wiley & Sons, Ltd.

doi: 10.1002/jlcr.669pmid: N/A

The original article to which this Erratum refers was published in Journal of Labelled Compounds and Radiopharmaceuticals 45 (7) 2002, 619–627.