Original Article

Journal of Investigative Dermatology (1984) 83, 105–109; doi:10.1111/1523-1747.ep12263272

Structure-Activity Relationships of Retinoids in the Morphogenesis of Cutaneous Appendages in the Chick Embryo

Rachida Cadi, Marie-Paule Pautou and Danielle Dhouailly

Equipe de recherche associée au CNRS 621, "Morphogenèse expérimentale," Laboratoire de Zoologie et Biologie animale, Université, scientifique et médicale de Grenoble, Saint Martin d'Hères Cedex, France

Received 5 December 1983; Accepted 14 March 1984.

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Abstract

We have evaluated the efficacy of 13 analogues of retinoic acid (retinoids) in producing in vivo feathers on the normally scaly foot integument (ptilopody) of the chick embryo. The retinoids were dissolved in dimethylsulfoxide and injected at doses from 1.25–250 mug into the amniotic cavity of embryos of 10 days of incubation. The results showed that the production of ptilopody requires specific retinoids, namely, those incorporating a free trans carboxylic end group. Indeed, the esterification of this acid end group (retinoids ethyl ester) leads to a delay in the effect of the product. Its substitution by an alcohol (retinol) or an aldehyde group (retinal), or its isomerization, leads to inactive products. The esterification by acetic acid of the alcohol terminal group of retinol leads to a moderately active compound (retinyl acetate). By contrast, modifications of the ring do not interfere with the efficacy of the retinoid, and modifications of the side chain by addition of one or two supplementary rings lead to an increase of the activity.

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