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Cited by 36Synthesis and biological activitySkin Protection and AgingFree Radicals and Antioxidants

Design, synthesis and biological evaluation of novel hydroxy-phenyl-1H-benzimidazoles as radical scavengers and UV-protective agents

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Bino, Alessia, Baldisserotto, Anna, Scalambra, Emanuela, Dissette, Valeria, Vedaldi, Daniela Ester, Salvador, Alessia, Durini, Elisa, Manfredini, Stefano +1 more·2017·Journal of Enzyme Inhibition and Medicinal Chemistry
DOI 10.1080/14756366.2016.1265523PMC PMC6010047
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Abstract

An ever-increasing incidence of skin neoplastic diseases is registered. Therefore, it is important to protect the skin from the UV radiation that reaches the epidermis and dermis but also to block ROS generated by them. Our attention was attracted in developing new compounds provided with both UV filtering and antioxidant capacities. To this end, 2-phenyl-1H-benzimidazole-5-sulfonic acid (PBSA), a known UV filter, was selected as lead compound for its lack of antioxidant activity, high water solubility and good safety profile. PBSA was sequentially modified introducing hydroxyls on the phenyl ring and also substituting the functional group in position 5 of the benzimidazole ring. At the end of the synthetic study, a new, very potent class of antioxidants has been obtained. Surprisingly some of the developed molecules, while devoid of significant UV-filtering activity was endowed with potent UV-filtering booster capability if associated with known commercial UVB and UVA filters.

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  • Benzimidazole derivatives 73-86 have photoprotective activity, and compound 83 also demonstrated antioxidant activity and higher photostability (98.4%) compared with control PBSA (14) (96.7%).

    “Benzimidazole derivatives 73–86 were reported for their photoprotective activity, and compound 83 also demonstrated antioxidant activity and higher photostability (98.4%) when compared with the control phenylbenzimidazole sulfonic acid (PBSA) (14) (96.7%) [134].”

    From UV Filters: Challenges and Prospects (2022) · cites this paper as [134]

    The Photostability and stability studies section reports 98.4% residual product for compound 12 versus 96.7% for PBSA; the Conclusions also identify compound 12 as antioxidant and photoprotective. The source uses compound numbers 2–15 rather than 73–86, so the identification of 83 as compound 12 is inferred from the numbering. More importantly, the Cytotoxicity and phototoxicity tests section says five compounds were unsuitable for further development as photoprotective agents, so the claim overstates the activity of the whole series. (LLM, conf=0.86)

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References 29 · Cited by 36

Research works printed but not linked: 28

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Authors
Bino, A., Baldisserotto, A., Scalambra, E., Dissette, V., Vedaldi, D. E., Salvador, A., Durini, E., Manfredini, S., & Vertuani, S.
Affiliations
  • University of Ferrara (IT)
  • University of Padua (IT)
Corresponding author
Manfredini, Stefano
ORCID
Venue
Journal of Enzyme Inhibition and Medicinal Chemistry
Publisher
Informa UK Limited
Published
2017-01-01
Volume
32
Issue
1
Pages
527-537
ISSN
  • 1475-6366 (ISSN-L)
  • 1475-6374
DOI
10.1080/14756366.2016.1265523
PMC
PMC6010047
OpenAlex
W2580721735
Cited by
36
References
29
Citations by year
2026: 2 · 2025: 3 · 2024: 4 · 2023: 5 · 2022: 5 · 2021: 4 · 2020: 6 · 2019: 6 · 2018: 1
FWCI
1.49
Type
journal article
Language
en
Open access
Licence
Locations
  • Journal of Enzyme Inhibition and Medicinal Chemistry (publishedVersion, cc-by)
  • Europe PMC (PubMed Central) (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
  • Institutional Research Information System University of Ferrara (University of Ferrara) (submittedVersion, other-oa)
Funders
  • Ministry of Education, University and Research (PRIN, Grant 20105YY2HL_006)
  • Ambrosialab srl (Grant year 2015)
  • University of Ferrara (FAR grant years 2010-2013)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
  • Health Sciences › Medicine › Dermatology › Skin Protection and Aging
  • Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Keywords
UV filters, radical scavengers, antioxidants, UV protection, reactive oxygen species, skin cancer prevention, structure-activity relationship, benzimidazole derivatives
MeSH terms
Antioxidants, Benzimidazoles, Cell Survival, Cells, Cultured, Dose-Response Relationship, Drug, Humans, Structure-Activity Relationship, Sunscreening Agents, Ultraviolet Rays, Drug Design, Molecular Structure, Free Radical Scavengers, Cell Proliferation

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