Martin C A, Dawson M I, McCormick A M, Napoli J L
Biochem Biophys Res Commun. 1986 Feb 26;135(1):124-30. doi: 10.1016/0006-291x(86)90951-4.
Two C(5)-azido substituted aromatic retinoids were evaluated as photoaffinity probes for studying the mechanism of retinoid action. The secondary azide 1 and the tertiary azide 2 were equipotent with the parent C(5)-geminal-dimethyl substituted aromatic retinoid 3 in stimulating F9-cell differentiation. Both azides bound covalently to cellular retinoic acid-binding protein upon photolysis, but the secondary azide was twice as efficient, likely because of lesser steric hindrance. The covalent binding of azide 1 was specific, since it was inhibited by retinoic acid. Thus substitution of a photolabile group onto aromatic retinoids does not abolish biological activity and affinity for cellular retinoic acid-binding protein.
评估了两种C(5)-叠氮基取代的芳香族视黄酸作为光亲和探针，用于研究视黄酸作用机制。仲叠氮化物1和叔叠氮化物2在刺激F9细胞分化方面与母体C(5)-偕二甲基取代的芳香族视黄酸3具有同等效力。两种叠氮化物在光解后均与细胞视黄酸结合蛋白共价结合，但仲叠氮化物的效率是叔叠氮化物的两倍，这可能是由于空间位阻较小。叠氮化物1的共价结合具有特异性，因为它受到视黄酸的抑制。因此，在芳香族视黄酸上取代一个光不稳定基团不会消除其生物活性和对细胞视黄酸结合蛋白的亲和力。
