Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives

[img]PDF - Authorized users only
Language: English
49Kb
Title:Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives
Creators:
Lapčík, Oldřich
Hampl, Richard
Hill, Martin
Stárka, Luboslav
Kasal, Alexander
Pouzar, Vladimír
Putz, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 5, pp. 799-807
Uncontrolled Keywords:Radioimmunoassay, Tyrosine methyl esters, Radioiodination, Steroid carboxymethyl derivatives

Abstract

Pure 3<i>Z</i> (<i>syn</i>) and 3<i>E</i> (<i>anti</i>) stereoisomers of testosterone 3-[<i>O</i>-(2-carboxyethyl)]oxime were synthesized, separated by HPLC or TLC, and used for preparation of tyrosine methyl ester (TME) conjugates by using mixed anhydride or carbodiimide-<i>N</i>-hydroxysuccinimide methods. While the latter method provided more than 96% of product with retained configuration, the mixed anhydride method yielded a mixture containing 26-40% of the opposite stereoisomer. The stereoisomers were used as model compounds, to which the other steroid TMEs and the corresponding radioiodinated products could be aligned according to their chromatographic properties. The TME conjugates of 3-(<i>O</i>-carboxymethyl)oximes of seven 4-en-3-oxo steroids were further prepared by carbodiimide-<i>N</i>-hydroxysuccinimide method. With exception of cortisol, the stereoisomeric (<i>Z</i> and <i>E</i>) radioiodinated TME conjugates could be separated by TLC. In addition, the conjugates with TME and consequently radioiodinated tracers were synthesized from hemisuccinates of cortisol and its 11α-isomer, via 11β- and 11α-hydroxy group. The radioiodinated conjugates were tested as radioligands with rabbit polyclonal antisera raised by using position-homologous conjugates of the respective steroid carboxy derivatives with bovine serum albumin as immunogens. With the exception of 11-deoxycorticosterone, the stereoisomeric <i>Z</i> and <i>E</i> radioiodinated TMEs did not differ in their binding properties. In the case of isomeric cortisol tracers conjugated through position 11 the antisera recognized only the sterically homologous radioligands, but the specificity of the system was poor.

Title:Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives
Creators:
Lapčík, Oldřich
Hampl, Richard
Hill, Martin
Stárka, Luboslav
Kasal, Alexander
Pouzar, Vladimír
Putz, Zdeněk
Uncontrolled Keywords:Radioimmunoassay, Tyrosine methyl esters, Radioiodination, Steroid carboxymethyl derivatives
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:5
Page Range:pp. 799-807
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960799UNSPECIFIED
ID Code:981
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Lapčík, Oldřich; Hampl, Richard; Hill, Martin; Stárka, Luboslav; Kasal, Alexander; Pouzar, Vladimír; Putz, Zdeněk (1996) Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives. Collection of Czechoslovak Chemical Communications, 61 (5). pp. 799-807. ISSN 0010-0765

Repository Staff Only: item control page