The stability of methyl-, ethyl- and fluoroethylesters against carboxylesterases in vitro: There is no difference

Nuclear Medicine and Biology

Volumn 38, Issue 1, 2011, Pages 13-17

  Nics, Lukas ^a,b   Haeusler, Daniela ^a,b   Wadsak, Wolfgang ^a,b   Wagner, Karl Heinz ^b   Dudczak, Robert ^a   Kletter, Kurt ^a   Mitterhauser, Markus ^a,b,c  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

Carboxylesterase (CES); EC 3.1.1.1; In vitro; Metabolism; Michaelis Menten kinetics

Indexed keywords

2 FLUOROETHYL 1 (1 PHENYLETHYL) 1H IMIDAZOLE 5 CARBOXYLIC ACID F 18; 2 FLUOROETHYL 1 PHENYLETHYL 4 (N PROPANOYLANILINO)PIPERIDINE 4 CARBOXYLIC ACID F 18; 2 FLUOROETHYL 2,4 DIETHYL 3 METHYLSULFANYLCARBONYL 6 PHENYLPYRIDINE 5 CARBOXYLIC ACID F 18; 2 FLUOROETHYL 3 BETA (4 IODOPHENYL)TROPANE 2 BETA CARBOXYLIC ACID F 18; 2 FLUOROETHYL 8 FLUORO 5 METHYL 6 OXO 5,6 DIHYDRO 4H BENZO[F]IMIDAZO[1,5 A][1,4]DIAZEPINE 3 CARBOXYLIC ACID F 18; CARBOXYLESTERASE; CARFENTANIL; ETHYL 1 (1 PHENYLETHYL) 1H IMIDAZOLE 5 CARBOXYLIC ACID C 11; ETHYL 8 FLUORO 5 METHYL 6 OXO 5,6 DIHYDRO 4H BENZO[F]IMIDAZO[1,5 A][1,4]DIAZEPINE 3 CARBOXYLIC ACID C 11; ETOMIDATE; FLUMAZENIL; METHYL 1 (1 PHENYLETHYL) 1H IMIDAZOLE 5 CARBOXYLIC ACID C 11; METHYL 1 PHENYLETHYL 4 (N PROPANOYLANILINO)PIPERIDINE 4 CARBOXYLIC ACID C 11; METHYL 2,4 DIETHYL 3 METHYLSULFANYLCARBONYL 6 PHENYLPYRIDINE 5 CARBOXYLIC ACID C 11; METHYL 3 BETA (4 IODOPHENYL)TROPANE 2 BETA CARBOXYLIC ACID C 11; METOMIDATE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STABILITY; DRUG STRUCTURE; ENZYME MECHANISM; IN VITRO STUDY; INCUBATION TIME; ISOTOPE LABELING; MICHAELIS CONSTANT; STRUCTURE ANALYSIS;

CARBOXYLESTERASE; CARBOXYLIC ACIDS; DRUG STABILITY; ESTERS; KINETICS; RADIOACTIVE TRACERS; SUBSTRATE SPECIFICITY;

EID: 78650995943     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.07.004     Document Type: Article

References (11)

1. Satoh T., Hosokawa M. The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 1998, 38:257-288.
2. Satoh T., Hosokawa M. Structure, function and regulation of carboxylesterases. Chem Biol Interact 2006, 162(3):195-211.
3. Stoops J.K., Hamilton S.E., Zerner B. Carboxylesterases (EC 3.1.1). A comparison of some kinetic properties of horse, sheep, chicken, pig, and ox liver carboxylesterases. Can J Biochem 1975, 53(5):565-573.
4. Mentlein R., Heiland S., Heymann E. Simultaneous purification and comparative characterization of six serine hydrolases from rat liver microsomes. Arch Biochem Biophys 1980, 200(2):547-559.
5. Ettlinger D.E., Wadsak W., Mien L.K., Machek M., Wabnegger L., Rendl G., et al. [18F]FETO: metabolic considerations. Eur J Nucl Med Mol Imaging 2006, 33(8):928-931.
6. Ettlinger D.E., Haeusler D., Wadsak W., Girschele F., Sindelar K.M., Mien L.K., et al. Metabolism and autoradiographic evaluation of [18F]FE@CIT: a comparison with [123I]beta-CIT and [123I]FP-CIT. Nucl Med Biol 2008, 35(4):475-479.
7. Haeusler D., Nics L., Mien L.K., Ungersboeck J., Lanzenberger R.R., Shanab K., et al. [18F]FE@SUPPY and [18F]FE@SUPPY:2 metabolic considerations. Nucl Med Biol 2010, 37(4):421-426.
8. Nics L., Haeusler D., Mien L.K., Wadsak W., Ettlinger D.E., El-Samahi H., et al. On the stability of radiolabelled esters: a carboxylesterase assay. Eur J Nucl Med Mol Imaging 2009, 36(suppl.2):S395. [abstract].
9. Shanab K., Wadsak W., Mien L.K., Mitterhauser M., Holzer W., Polster V., et al. Synthesis of in vivo metabolites of the new adenosine A3 receptor PET-radiotracer [18F]FE@SUPPY. Heterocycles 2008, 75(2):339-356.
10. Theodoridis G. Novel applications of alkyl fluorides in organic synthesis: versatile nitrogen protecting groups. Tetrahedron Lett 1998, 39(51):9365-9368.
11. Wadsak W., Mien L.K., Ettlinger D.E., Eidherr H., Haeusler D., Sindelar K.M., et al. 18F fluoroethylations: different strategies for the rapid translation of 11C-methylated radiotracers. Nucl Med Biol 2007, 34(8):1019-1028.