Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative

Hyojung Kim, Bora Kim, Hyuk Kim, Soojong Um, Joodong Lee, Heechang Ryoo, Hyungil Jung

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

A new hybrid, retinyl retinoate 1, was synthesized with a condensing reaction between retinol and retinoic acid to improve the photo-stability, and the in vitro biological activity of the hybrid was analyzed. This retinol derivative had enhanced thermal stability and decreased photosensitivity, and exhibited decreased cell toxicity compared to that of retinol. In addition, RAR activity analysis showed that retinyl retinoate 1 had higher inhibitory activity against c-Jun than retinol and showed superior effects on collagen synthesis compared to retinol. Thus, retinyl retinoate 1 may have the potential to be conveniently used as an additive in cosmetics for prevention and improvement of skin aging and medicines for the treatment of skin troubles due to its excellent stability under severe and accelerated conditions.

Original languageEnglish
Pages (from-to)6387-6393
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number12
DOIs
Publication statusPublished - 2008 Jun 15

Fingerprint

Retinoids
Bioactivity
Vitamin A
Derivatives
Skin
Skin Aging
Photosensitivity
Cosmetics
Tretinoin
Medicine
Toxicity
Thermodynamic stability
Collagen
Hot Temperature
Aging of materials
retinyl retinoate
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Kim, Hyojung ; Kim, Bora ; Kim, Hyuk ; Um, Soojong ; Lee, Joodong ; Ryoo, Heechang ; Jung, Hyungil. / Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 12. pp. 6387-6393.
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Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative. / Kim, Hyojung; Kim, Bora; Kim, Hyuk; Um, Soojong; Lee, Joodong; Ryoo, Heechang; Jung, Hyungil.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 12, 15.06.2008, p. 6387-6393.

Research output: Contribution to journalArticle

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AB - A new hybrid, retinyl retinoate 1, was synthesized with a condensing reaction between retinol and retinoic acid to improve the photo-stability, and the in vitro biological activity of the hybrid was analyzed. This retinol derivative had enhanced thermal stability and decreased photosensitivity, and exhibited decreased cell toxicity compared to that of retinol. In addition, RAR activity analysis showed that retinyl retinoate 1 had higher inhibitory activity against c-Jun than retinol and showed superior effects on collagen synthesis compared to retinol. Thus, retinyl retinoate 1 may have the potential to be conveniently used as an additive in cosmetics for prevention and improvement of skin aging and medicines for the treatment of skin troubles due to its excellent stability under severe and accelerated conditions.

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