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A Multitarget Approach toward the Development of 8‐Substituted Purines for Photoprotection and Prevention of UV‐Related Damage
Author(s) -
Djuidje Ernestine N.,
Dissette Valeria,
Bino Alessia,
Benetti Simonetta,
Balzarini Jan,
Liekens Sandra,
Manfredini Stefano,
Vertuani Silvia,
Baldisserotto Anna
Publication year - 2017
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201700137
Subject(s) - photoprotection , antioxidant , dpph , uv filter , chemistry , scavenger , ultraviolet , antifungal , photochemistry , combinatorial chemistry , biochemistry , dermatology , materials science , medicine , optoelectronics , photosynthesis , physics , optics
Ultraviolet (UV) light is the most abundant and significant modifiable risk factor for skin cancer and many other skin diseases such as early photo‐aging. Across the solar radiation spectrum, UV light is the main cause behind skin problems. In the search for novel photoprotective compounds, a new series of 8‐substituted purines were synthesized from commercially available 6‐hydroxy‐4,5‐diaminopyrimidine hemisulfate or 4,5‐diaminopyrimidine. All title compounds were investigated for their UV filtering, antioxidant, antifungal, and antiproliferative activities. For the photoprotection assays we used a diffuse transmittance technique to determine the sun protection factor (SPF) in vitro, and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and ferric ion reducing antioxidant power (FRAP) tests for evaluating the antioxidant activity of the more potent compounds. Among them, 8‐(2,5‐dihydroxyphenyl)‐7 H ‐purin‐6‐ol (compound 26 ) proved to be a good radical scavenger and is also endowed with broad‐spectrum UVA filtering capabilities, suitable for further development as a protective molecule.