Retinoids

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Retinoids are chemical substances that are related to retinol (vitamin A) in their chemical structure or in their biological activity .

History of definition

The IUPAC- IUB Commission for Biochemical Nomenclature defined the term “retinoids” in 1982 as a “class of components consisting of four isoprene units that are in a head-to-tail connection; all retinoids can be formally derived from a monocyclic parent component that contain five C = C double bonds and a functional group at the acyclic end of the molecule. ”However, in the 1980s, synthetic components were found that did not meet these defined structural requirements in various retinoids -sensitive biological assays were much more active than retinol . As a supplementary or substitute definition, it was proposed in 1985 that “retinoids are a class of substances that cause specific biological responses by binding to and activating receptors”.

In the meantime, some retinoids are also known that have been shown not to develop their biological activity through the involvement of receptors.

Retinoids used therapeutically

Selected retinoids are used in humans for medical and therapeutic purposes. There are currently three generations of therapeutic retinoids:

1st generation (non-aromatic retinoids) : The non-aromatic retinoids include tretinoin ( all-trans-retinoic acid ) and its isomer isotretinoin ( 13-cis-retinoic acid ), which are used both systemically and topically . Both arise naturally in comparatively small quantities in the vitamin A metabolism of humans. Further, even that will Alitretinoin ( 9-cis-retinoic acid ) are used for treatment.

2nd generation (monoaromatic retinoids) : Monoaromatic retinoids are acitretin , etretinate and motretinide .

3rd generation (polyaromatic retinoids) : Polyaromatic retinoids are adapalene , arotenoid , acetylene retinoids and tazarotene .

4th generation : Trifaroten

Individual evidence

  1. ↑ Arnhold: The term "retinoids" In: Studies on the metabolism of vitamin A / retinoids with regard to a risk assessment of their teratogenic effects in humans ; P. 2; Dissertation; Braunschweig, March 7, 2000. Full text
  2. ^ DL Newton, WR Henderson, MB Sporn: Structure-activity relationships of retinoids in hamster tracheal organ culture . In: Cancer Res . 40 (1980) 3413-3425.
  3. ↑ MB Sporn, AB Roberts: What is a retinoid? . In: Ciba. Found. Symp. 113: 1-5 (1985).
  4. ↑ BP Sani, Shealy YF, DL Hill: N- (4-hydroxyphenyl) retinamide: interactions with retinoid-binding proteins / receptors. In: Carcinogenesis, 16 : 2531-253 (1995).
  5. ^ AC Ross, UG Hämmerling: Retinoids and the immune system . In: MB Sporn, AB Roberts, DS Goodman (Eds.): The Retinoids. Biology, Chemistry, and Medicine . Raven Press, New York, 1994, pp. 521-543.

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