Buku A, Yamin N, Gazis D
Department of Physiology and Biophysics, Mount Sinai School of Medicine of CUNY, New York 10029.
Peptides. 1988 Jul-Aug;9(4):783-6. doi: 10.1016/0196-9781(88)90122-2.
This study reports the solid phase synthesis and biological activities of two oxytocin analogs, [1-desamino, 4-lysine,7-(L-3,4,-dehydroproline)]oxytocin and [1-desamino, 4-threonine,7-(L-3,4-dehydroproline),8-lysine]oxytocin, and several fluorescent, photoaffinity, or biotinylated derivatives of these analogs and of oxytocin. The activities (in IU/mg) of the lysine-containing parent compounds, respectively, were as follows: uterus (without Mg++) 4.8 and 54; uterus (with Mg++) 19 and 440; milk ejection 65 and 414. The above analogs were coupled through the chemically reactive epsilon-amino group of lysine in position 4 or 8 or, in the case of oxytocin, through the N-terminal amino group of fluoresceine, photoaffinity, or biotinyl ligands. Fluoresceine coupled in position 1 of oxytocin gave an analog of low to moderate uterine (3.8 without Mg+ and 1.9 with Mg++) and milk ejection (7.9) activities. Analogs with biotin or fluoresceine coupled to lysine in position 4 had moderate uterine (11 and 23 without Mg++; 38 and 11 with Mg++) and milk ejection (33 and 13) activities. Analogs with fluoresceine, photoaffinity, or biotinyl labels coupled to lysine in position 8 retained good uterine (106, 62, and 147 without Mg++; 79, 78, and 509 with Mg++) and milk ejection (101, 181, and 247) activities and represent potentially useful experimental tools for studying hormone-receptor interactions and for receptor localization and isolation.
本研究报告了两种催产素类似物，即[1-去氨基，4-赖氨酸，7-(L-3,4-脱氢脯氨酸)]催产素和[1-去氨基，4-苏氨酸，7-(L-3,4-脱氢脯氨酸)，8-赖氨酸]催产素，以及这些类似物和催产素的几种荧光、光亲和或生物素化衍生物的固相合成及生物活性。含赖氨酸的母体化合物的活性（以IU/mg计）分别如下：子宫（无Mg++）4.8和54；子宫（有Mg++）19和440；排乳65和414。上述类似物通过4位或8位赖氨酸的化学反应性ε-氨基进行偶联，对于催产素而言，则通过荧光素、光亲和或生物素配体的N端氨基进行偶联。在催产素1位偶联荧光素得到的类似物，其子宫活性低至中等（无Mg+时为3.8，有Mg++时为1.9），排乳活性为7.9。生物素或荧光素与4位赖氨酸偶联的类似物，其子宫活性中等（无Mg++时为11和23；有Mg++时为38和11），排乳活性为33和13。荧光素、光亲和或生物素标签与8位赖氨酸偶联的类似物，保留了良好的子宫活性（无Mg++时为106、62和147；有Mg++时为79、78和509）和排乳活性（101、181和247），是研究激素-受体相互作用以及受体定位和分离的潜在有用实验工具。
