Structure-activity relationships of retinoids in the morphogenesis of cutaneous appendages in the chick embryo. 1984

R Cadi, and M P Pautou, and D Dhouailly

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 micrograms 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 (retinoid 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.

UI MeSH Term Description Entries
D009024 Morphogenesis The development of anatomical structures to create the form of a single- or multi-cell organism. Morphogenesis provides form changes of a part, parts, or the whole organism.
D002642 Chick Embryo The developmental entity of a fertilized chicken egg (ZYGOTE). The developmental process begins about 24 h before the egg is laid at the BLASTODISC, a small whitish spot on the surface of the EGG YOLK. After 21 days of incubation, the embryo is fully developed before hatching. Embryo, Chick,Chick Embryos,Embryos, Chick
D004121 Dimethyl Sulfoxide A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation. DMSO,Dimethyl Sulphoxide,Dimethylsulfoxide,Dimethylsulphinyl,Dimethylsulphoxide,Dimexide,Rheumabene,Rimso,Rimso 100,Rimso-50,Sclerosol,Sulfinylbis(methane),Rimso 50,Rimso50,Sulfoxide, Dimethyl,Sulphoxide, Dimethyl
D004305 Dose-Response Relationship, Drug The relationship between the dose of an administered drug and the response of the organism to the drug. Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D005241 Feathers Flat keratinous structures found on the skin surface of birds. Feathers are made partly of a hollow shaft fringed with barbs. They constitute the plumage. Feather
D005528 Foot The distal extremity of the leg in vertebrates, consisting of the tarsus (ANKLE); METATARSUS; phalanges; and the soft tissues surrounding these bones. Feet
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D012176 Retinoids A group of tetraterpenes, with four terpene units joined head-to-tail. Biologically active members of this class are used clinically in the treatment of severe cystic ACNE; PSORIASIS; and other disorders of keratinization. Retinoid
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013997 Time Factors Elements of limited time intervals, contributing to particular results or situations. Time Series,Factor, Time,Time Factor

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