Shealy Y F, Frye J L, Schiff L J
Southern Research Institute, Birmingham, Alabama 35255.
J Med Chem. 1988 Jan;31(1):190-6. doi: 10.1021/jm00396a031.
N-(all-trans-Retinoyl)amino acids were synthesized via all-trans-retinoyl chloride and an ester of the amino acid. The retinoyl derivatives of leucine, phenylalanine, alanine, tyrosine, and glutamic acid were prepared. The 13-cis-retinoyl derivatives of leucine, phenylalanine, alanine, and glycine were prepared similarly from 13-cis-retinoic acid. In assays of the retinoylamino acids for reversal of squamous metaplasia in hamster trachea organ cultures, these compounds were less active than retinoic acid, but the leucine, alanine, and phenylalanine derivatives were similar in activity to several retinamides that suppress bladder carcinogenesis in vivo. Two of the retinoylamino acids, as well as two simple retinamides, were shown to be moderately cytotoxic to murine leukemia and human epidermoid carcinoma cells in culture.
通过全反式视黄酰氯和氨基酸酯合成了N -（全反式视黄酰基）氨基酸。制备了亮氨酸、苯丙氨酸、丙氨酸、酪氨酸和谷氨酸的视黄酰衍生物。类似地，由13 - 顺式视黄酸制备了亮氨酸、苯丙氨酸、丙氨酸和甘氨酸的13 - 顺式视黄酰衍生物。在仓鼠气管器官培养中检测视黄酰氨基酸逆转鳞状化生的实验中，这些化合物的活性低于视黄酸，但亮氨酸、丙氨酸和苯丙氨酸衍生物的活性与几种在体内抑制膀胱癌发生的视黄酰胺相似。已表明其中两种视黄酰氨基酸以及两种简单的视黄酰胺在培养中对小鼠白血病细胞和人表皮样癌细胞具有中等细胞毒性。
