Synthesis, antioxidant and photoprotection activities of hybrid derivatives useful to prevent skin cancer
Abstract
Chronic ultraviolet (UV) radiation exposure is a major cause of skin cancer. A novel series of hybrid derivatives (I-VIII) for use in sunscreen formulations were synthesized by molecular hybridization of t-resveratrol, avobenzone, and octyl methoxycinnamate, and were characterized. The antioxidant activity values for VIII were comparable than to those of t-resveratrol. Compounds I-III and VI demonstrated Sun Protector Factor superior to that of t-resveratrol. Compounds I and IV-VIII were identified as new, broad-spectrum UVA filters while II-III were UVB filters. In conclusion, novel hybrid derivatives with antioxidant effects have emerged as novel photoprotective agents for the prevention of skin cancer.
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Compounds 128 and 131-135 possess characteristics of broad-spectrum molecules, with 128, 134, and 135 having interesting DPPH radical scavenging activity.
“Amongst all, compounds 128 and 131–135 possess characteristics of broad-spectrum molecules, having 128, 134, and 135 an interesting DPPH radical scavenging activity.”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [138]
Three hybrids among 128-135 (compounds 128, 134, and 135) possess antioxidant potential, with IC50 between 88 μM and 275 μM.
“Additionally, three hybrids of the total synthetised compounds 128–135 possess antioxidant potential, with an IC50 between 88 µM and 275 µM (compounds 128, 134, and 135) [138].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [138]
Molecular hybridisation of avobenzone (11), EHMC (21), and trans-resveratrol (40) resulted in a novel series of hybrids (128-135) with UV filter effect.
“Molecular hybridisation avobenzone (11), EHMC (21), and trans-resveratrol (40) resulted in the identification of a novel series of hybrids (128–135) with UV filter effect [138].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [138]
All hybrids 128-135 revealed photoprotective activity with SPF values between 2 and 5 and ability to absorb UVA region, confirmed by λmax values in the range of 369 nm and 389 nm.
“All compounds revealed photoprotective activity with SPF values varied between 2 and 5, and an ability to absorb the UVA region of the electromagnetic spectrum, confirmed by their λmax values in the range of 369 nm and 389 nm [138].”
From UV Filters: Challenges and Prospects (2022) · cites this paper as [138]
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- Authors
- Reis, J. S., Corrêa, M. A., Chung, M. C., & dos Santos, J. L.
- Affiliations
- Universidade Estadual Paulista (Unesp) (BR)
- Venue
- Bioorganic & Medicinal Chemistry
- Publisher
- Elsevier BV
- Published
- 2014-05
- Volume
- 22
- Issue
- 9
- Pages
- 2733-2738
- ISSN
- 0968-0896 (ISSN-L)
- OpenAlex
- W2019624009
- Cited by
- 33
- References
- 32
- Citations by year
- 2026: 2 · 2024: 2 · 2023: 3 · 2022: 5 · 2021: 3 · 2020: 3 · 2019: 4 · 2018: 2 · 2017: 3 · 2016: 4 · 2014: 2
- FWCI
- 3.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Bioorganic & Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Acervo Digital da Universidade Estadual Paulista (Universidade Estadual Paulista) (submittedVersion)
- UNESP Institutional Repository (São Paulo State University) (submittedVersion)
- Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo (2012/09237-0)
- Topics
- Health Sciences › Medicine › Dermatology › Skin Protection and Aging
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Health Sciences › Medicine › Pharmacology › Synthesis of Organic Compounds
- Keywords
- hybrid derivatives, UV filters, photoprotection, skin cancer prevention, antioxidant activity, avobenzone, octyl methoxycinnamate, molecular hybridization, UVA filters, UVB filters, sun protection factor, ultraviolet radiation
- MeSH terms
- Resveratrol, Antioxidants, Cinnamates, Humans, Propiophenones, Skin Neoplasms, Stilbenes, Sunscreening Agents, Ultraviolet Rays, Sun Protection Factor
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