RETINOIDS IN DERMATOLOGY:FUNCTIONAL ACTIVITY AND PROSPECTS OF SYNTHETIC ANALOGUES V. B. Kovtun, O. G. Sidorenko, M. D. Khomiakova, I. A. Levandovskiy

Details: Hits: 791

ISSN 2410-7751 (Print)
ISSN 2410-776X (Online)

Biotechnologia Acta V. 13, No 5, 2020
Р. 32-41, Bibliography 33, English
Universal Decimal Classification: 615.275.4+615.277.3+615.276+615.262.1
https://doi.org/10.15407/biotech13.05.032

RETINOIDS IN DERMATOLOGY:FUNCTIONAL ACTIVITY AND PROSPECTS OF SYNTHETIC ANALOGUES

V. B. Kovtun¹, O. G. Sidorenko², M. D. Khomiakova³, I. A. Levandovskiy ¹

¹National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”
²LLC “PHARMA INTERNATIONAL GROUP 2”, Kyiv, Ukraine
³Gimnasium “Akademiia”, Kyiv, Ukraine

The aim of the work was to analyze and summarize information on the functional activity of known retinoids, as well as to determine the directions of their modification and prospects for the use of their synthetic analogues in dermatology.

The literature on retinoids metabolism stages in the human body, the mechanisms of their action and the properties that determine their use in various medical fields was considered and analyzed. Information on dermatological diseases treatment with natural retinoids and their synthetic analogues was summarized.

The modern classification of retinoids based on the peculiarities of their chemical structure and functional activity is given, the relationship between these characteristics and the direction of use of such drugs in dermatology and cosmetology is shown.

Prospects for the practical application of synthetic retinoids represented mainly by polyaromatic compounds are due to their higher stability and efficiency, as well as reduced irritant effect due to selectivity for nuclear receptors.

Key words: retinoids, synthetic analogues of retinoids, mechanisms of biological activity, nuclear receptors of retinoids, dermatology.

References

1. Theodosiou M., Laudet V., Schubert M. From carrot to clinic: an overview of the retinoic acid signaling pathway. Cell. Mol. Life Sci. 2010, V. 67, P. 1423–1445. https://doi.org/10.1007/s00018-010-0268

2. Blomhoff R., Blomhoff H. K. Overview of retinoid metabolism and function. J. Neurobiol. 2006, V. 66, P. 606–630. https://doi.org/10.1002/neu.20242

3. Jager C. Vitamins and Brain Health. Vitamins & Trace Elements. 2013, 01 (01). https://doi.org/10.3390/nu8020068

4. Keys S., Zimmerman W. Antioxidant Activity of Retinol, Glutathione, and Taurine in Bovine Photoreceptor Cell Membranes. Experimental Eye Res. 1999, 68 (6), 693?702. https://doi.org/10.1006/exer.1999.0657

5. Tee E., Lim C. The analysis of carotenoids and retinoids: A review. Food Chemistry. 1991, 41 (2), 147?193. https://doi.org/10.1021/jf00108a049

6. Khalil S., Bardawil T., Stephan C., Darwiche N., Abbas O., Kibbi A., Nemer G., Kurban M. Retinoids: a journey from the molecular structures and mechanisms of action to clinical uses in dermatology and adverse effects. J. Dermatol. Treatment. 2017, 28 (8), 684?696. https://doi.org/10.1080/09546634.2017.1309349

7. Chaves G., Peres W., Gon?alves J., Ramalho A. Vitamin A and retinol-binding protein deficiency among chronic liver disease patients. Nutrition. 2015, 31 (5), 664?668. https://doi.org/10.1016/j.nut.2014.10.016

8. Elder J., ?str?m A., Pettersson U., Tavakkol A., Krust A., Kastner P., Chambon P., Voorhees J. Retinoic Acid Receptors and Binding Proteins in Human Skin. J. Investigative Dermatol. 1992, 98 (6), S36?S41. https://doi.org/10.1111/1523-1747.ep12462180

9. Daly A., Rees J., Redfern C. Nuclear Retinoic-Acid-Binding Proteins and Receptors in Retinoic-Acid-Responsive Cell Lines. Pathobiol. 1989, 57 (6), 339?345.https://doi.org/10.1159/000163547

10. Fisher G., Talwar H., Xiao J., Datta S., Reddy A., Gaub M., Egly C., Chambon P., Voorhees J. Immunological and functional quantitation of nuclear retinoid X (RXR) and retinoic acid (RAR) receptor proteins in human epidermis in vivo: High levels of RXRS and RAR-?, low levels of RAR-?, and absence of RAR-?. J. Dermatol. Sci. 1993, 6 (1), 53. https://doi.org/10.1016/0923-1811(93)91017-O

11. Dawson M. I., Zhang X., Hobbs P. D., Jong L. Synthetic retinoids and their usefulness in biology and medicine. In: Livrea M. A. (eds) Vitamin A and Retinoids: An Update of Biological Aspects and Clinical Applications. 2000MCBU. Molecular and Cell Biology. Updates. Birkh?user, Basel. https://doi.org/10.1007/978-3-0348-8454-9_14

12. B?vik C., Peterson P., Eriksson U. Retinol-Binding Protein Mediates Uptake of Retinol to Cultured Human Keratinocytes. Experimental Cell Res. 1995, 216 (2), 358?362. https://doi.org/10.1006/excr.1995.1045

13. Tanumihardjo S. Can Lack of Improvement in Vitamin A Status Indicators Be Explained by Little or No Overall Change in Vitamin A Status of Humans? J. Nutrition. 2001, 131 (12), 3316?3318. https://doi.org/10.1093/jn/131.12.3316

14. Fisher G., Voorhees J. Molecular mechanisms of retinoid actions in skin. FASEB J. 1996, 10 (9), 1002?1013. https://doi.org/10.1096/fasebj.10.9.8801161

15. Weiss J. Topical Tretinoin Improves Photoaged Skin. JAMA. 1988, 259 (4), 527. Baker M. From skin cell to stem cell. Nature Reports Stem Cells. 2007. https://doi.org/10.1001/jama.1988.03720040019020

16. Lohnes D., Mark M., Mendelsohn C., Doll? P., Decimo D., LeMeur M., Dierich A., Gorry P., Chambon P. Developmental roles of the retinoic acid receptors. J. Steroid Biochem. Mol. Biol. 1995, 53 (1?6), 475?486. https://doi.org/10.1016/0960-0760(95)00094-G

17. Molin S. C., Ruzicka T. Retinoids. In: John S., Johansen J., Rustemeyer T., Elsner P., Maibach H. (eds) Kanerva’s Occupational Dermatology. 2020. Springer, Cham.

18. Harrison E. H., Curley R. W. Carotenoids and Retinoids: Nomenclature, Chemistry, and Analysis. In: Asson-Batres M., Rochette-Egly C. (eds) The Biochemistry of Retinoid Signaling II. Subcellular Biochemistry. 2016, V. 81. Springer, Dordrecht. https://doi.org/10.1007/978-94-024-0945-1_1

19. Chandraratna R. Future trends: A new generation of retinoids. J. American Academy of Dermatol. 1998, 39 (4), S149?S152. https://doi.org/10.1016/S0190-9622(98)70313-5

20. Kawaguchi R., Zhong M., Kassai M., Ter-Stepanian M., Sun H. Differential and Isomer-Specific Modulation of Vitamin A Transport and the Catalytic Activities of the RBP Receptor by Retinoids. J. Membrane Biol. 2013, V. 246, P. 647–660. https://doi.org/10.1007/s00232-013-9578-z

21. Beckenbach L., Baron J. M., Merk H. F., L?ffler H., Amann P. M. Retinoid treatment of skin diseases. Eur. J. Dermatol. 2015, V. 25, P. 384–391. https://doi.org/10.1684/ejd.2015.2544

22. Marks R. Retinoids for the future: developing a new generation of receptor-selective retinoids. J. European Academy of Dermatol. Venerol. 1995, 5 (1), S189. https://doi.org/10.1016/0926-9959(95)96555-M

23. Ruzicka T., Larsen F., Galewicz D., Horv?th A., Coenraads P., Thestrup-Pedersen K. Oral Alitretinoin (9-cis-Retinoic Acid) Therapy for Chronic Hand Dermatitis in Patients Refractory to Standard Therapy. Archives Dermatol. 2004, 140 (12). https://doi.org/10.1001/archderm.140.12.1453

24. Stratigos A., Katsambas A. The Role of Topical Retinoids in the Treatment of Photoaging. Drugs. 2005, 65 (8), 1061?1072. https://doi.org/10.2165/00003495-200565080-00003

25. Guenther L., Kunynetz R., Lynde C., Sibbald R., Toole J., Vender R. et al. Acitretin Use in Dermatology. J. Cutaneous Medicine and Surgery. 2017, 21 (3 suppl), 2S?12S. https://doi.org/10.1177/1203475417733414

26. Larsen F., Jakobsen P., Larsen C., Kragballe K., Nielsen-Kudsk F. Pharmacokinetics of Etretin and Etretinate during Long-Term Treatment of Psoriasis Patients. Pharmacol. Toxicol. 1988, 62 (3), 159?165. https://doi.org/10.1111/j.1600-0773.1988.tb01865.x

27. Shi-Jun Shan, Yuan-Hong Li, Guowei Zhang, Ting Xiao, Changping Li, Huachen Wei, Hong-Duo Chen. Treatment of palmoplantar pustulosis with arotinoid ethylester. Europ. J. Dermatol. 2009, 19 (5), 474?477. https://doi.org/10.1684/ejd.2009.0727

28. Loss M. J., Leung S., Chien A., Kerrouche N., Fischer A., Kang S. Adapalene 0.3% Gel Shows Efficacy for the Treatment of Atrophic Acne Scars. Dermatol. Therapy. (Heidelb). 2018, V. 8, P. 245–257. https://doi.org/10.1007/s13555-018-0231-8

29. Abe M., Inoue C., Yokoyama Y., Ishikawa O. Successful Treatment of Darier’s Disease with Adapalene Gel. Pediatric Dermatol. 2010, 28 (2), 197?198. https://doi.org/10.1111/j.1525-1470.2009.01077.x

30. Frances L., Pascual J., Leiva-Salinas M., Betlloch I. Extramammary Paget disease successfully treated with topical imiquimod 5% and tazarotene. Dermatol. Therapy. 2013, 27 (1), 19?20. https://doi.org/10.1111/dth.12030

31. Cao H., Bissinger R., Umbach A., Gawaz M., Lang F. Effect of Bexarotene on Platelet Activation and Apoptosis. Cellular Physiol. Biochem. 2017, 42 (2), 838?847. https://doi.org/10.1159/000478627

32. Lewis D., Huang S., Duvic M. Oral bexarotene for post-transplant cutaneous T-cell lymphoma. Dermatol. Therapy. 2017, 30 (5), e12524. https://doi.org/10.1111/dth.12524

33. Heo J., Jung T., Lee S., Kim H., Choi G., Jung M. Effect of bexarotene on differentiation of glioblastoma multiforme compared with ATRA. Clin. Experimental Metastasis. 2016, 33 (5), 417?429. https://doi.org/10.1007/s10585-016-9786-x