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

References

• Brenner M, Hearing VJ. The protective role of melanin against UV damage in human skin. Photochem Photobiol 2008;84:539–49.
   PubMed Web of Science ®Google Scholar
• Koulu L. UV radiation, tanning and DNA damage. Duodecim 2014;130:637–41.
   Google Scholar
• Mukhtar H, Elmets CA. Photocarcinogenesis: mechanisms, models and human health implications. Photochem Photobiol 1996;63:356–7.
   PubMed Web of Science ®Google Scholar
• Knak A, Regensburger J, Maisch T, Bäumler W. Exposure of vitamins to UVB and UVA radiation generates singlet oxygen. Photochem Photobiol Sci 2014;13:820–9.
   PubMed Web of Science ®Google Scholar
• Longstreth J, de Gruijl FR, Kripke ML, et al. Health risks. J Photochem Photobiol B Biol 1998;46:20–39.
   PubMed Web of Science ®Google Scholar
• Gasparro FP, New perspectives in sunscreen photobiology. ed. Molecular, cellular and physiological aspects. Berlin: Springer-Verlag; 1997:177–186.
   Google Scholar
• Bastuji-Garin S, Diepgen TL. Cutaneous malignant melanoma, sun exposure and sunscreen use: epidemiological evidence. Br J Dermatol 2002;146:24–30.
   PubMed Web of Science ®Google Scholar
• Reis JS, Corrêa MA, Chung MC, Dos Santos JL. Synthesis, antioxidant and photoprotection activities of hybrid derivatives useful to prevent skin cancer. Bioorg Med Chem 2014;22:2733–8.
   PubMed Web of Science ®Google Scholar
• Yaar M, Gilchrest BA. Ageing and photoageing of keratinocytes and melanocytes. Clin Exp Dermatol 2001;26:583–91.
   PubMed Web of Science ®Google Scholar
• Yaar M, Gilchrest BA. Photoageing: mechanism, prevention and therapy. Br J Dermatol 2001;157:874–87.
   Web of Science ®Google Scholar
• Oppel T, Korting HC. Actinic keratosis: the key event in the evolution from photoaged skin to squamous cell carcinoma. Therapy based on pathogenetic and clinical aspects. Skin Pharmacol Physiol 2004;17:67–76.
   PubMed Web of Science ®Google Scholar
• Forestier S. Rationale for sunscreen development. J Am Acad Dermatol 2008;58:133–8.
   PubMed Web of Science ®Google Scholar
• Serpone N, Salinaro A, Emeline AV, et al. An in vitro systematic spectroscopic examination of the photostabilities of a random set of commercial sunscreen lotions and their chemical UVB/UVA active agents. Photochem Photobiol Sci 2002;1:970–81.
   PubMed Web of Science ®Google Scholar
• Vertuani S, Baldisserotto A, Scalambra E, et al. Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities. Eur J Med Chem 2012;50:383–92.
   PubMed Web of Science ®Google Scholar
• Stevenson C, Davies RJH. Photosensitization of guanine-specific DNA damage by 2-phenylbenzimidazole and the sunscreen agent 2-phenylbenzimidazole-5-sulfonic Acid. Chem Res Toxicol 1999;12:38–45.
   PubMed Web of Science ®Google Scholar
• Inbaraj JJ, Bilski P, Chignell CF. Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic Acid. Photochem Photobiol 2002;75:107–16.
   PubMed Web of Science ®Google Scholar
• da Silva MF, Signorini AM, Vincente J, et al. Synthesis of substituted dipyrido[3,2-a:20,30-c]phenazines and a new heterocyclicdipyrido[3,2-f:20,30-h]quinoxalino[2,3-b]quinoxaline. Tetrahedron 2008;64:5410–15.
   Web of Science ®Google Scholar
• Secci D, Bolasco A, D’Ascenzio M, et al. Conventional and microwave-assisted synthesis of benzimidazole derivatives and their in vitro inhibition of human cyclooxygenase. J Heterocyclic Chem 2012;49:1187–95.
   Web of Science ®Google Scholar
• Pomel S, Dubar F, Forge D, et al. New heterocyclic compounds: synthesis and antitrypanosomal properties. Bioorg Med Chem 2015;23:5168–74.
   PubMed Web of Science ®Google Scholar
• Manfredini S, Vertuani S, Scalambra E. Patent WO2013102843 A2.
   Google Scholar
• Jung HY, Park MH, Ha YM, et al. Patent KR 2012091651; 2012.
   Google Scholar
• Goeker H, Oelgen S, Ertan R, et al. Synthesis of some new benzimidazole-5(6)-carboxylic acids. J Heterocycl Chem 1995;32:1767–73.
   Web of Science ®Google Scholar
• Popov I, Lewin G. Antioxidative homeostasis: characterization by means of chemiluminescent technique. Meth Enzymol 1999;300:437–56.
   PubMed Web of Science ®Google Scholar
• Popov I, Lewin G. Photochemiluminescent detection of antiradical activity; IV: testing of lipid-soluble antioxidants. J Biochem Biophys Methods 1996;31:1–8.
   PubMedGoogle Scholar
• Wang M, Li J, Rangarajan M, et al. Antioxidative phenolic compounds from Sage (Salvia officinalis). J Agric Food Chem 1998;46:4869–73.
   Web of Science ®Google Scholar
• Guihua X, Xing Qian Y, Jianchu C, Donghong L. Effect of heat treatment on the phenolic compounds and antioxidant capacity of citrus peel extract. J Agric Food Chem 2007;55:330–5.
   PubMed Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
   PubMed Web of Science ®Google Scholar
• Öztürk S, Akkurt M, Küçükbay H, et al. 3,3′-Diethyl-1,1′-butylenedi[5(6)-methyl-benzimidazolium] diiodide dihydrate. Acta Cryst 2003;E59:o1014–16.
   Google Scholar
• Elderfield R, Heterocyclic compounds. New York: Wiley and Sons; 1957.
   Google Scholar
• Duffy KJ, Price AT, Delorme E, et al. Identification of a pharmacophore for thrombopoietic activity of small, non-peptidyl molecules. 2. Rational design of naphtho[1,2-d]imidazolethrombopoietin mimics. J Med Chem 2001;45:3576–8.
   Web of Science ®Google Scholar
• Shaath NA, The chemistry of ultraviolet filters; monograph: Sunscreens: regulation and commercial Development. 3rd ed. Cosmetic science and technology series, Boca Raton, FL. 2005:218–238.
   Google Scholar
• Diffey BL, Robson J. A new substrate to measures sunscreen protection factors throughout the ultraviolets spectrum. J Soc Cosmet Chem 1989;40:127–33.
   Web of Science ®Google Scholar
• Vertuani S, Ziosi P, Solaroli N, et al. Determination of antioxidant efficacy of cosmetic formulations by non-invasive measurements. Skin Res Technol 2003;9:245–53.
   PubMed Web of Science ®Google Scholar
• BASF Sunscreen simulator. Available from: www.sunscreensimulator.basf.com/Sunscreen_Simulator [last accessed 16 Apr 2016].
   Google Scholar