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Research Articles

Synthesis of salicylic acid from wintergreen oil by green chemistry overcomes its cytotoxicity in keratinocyte cells and teratogenicity in zebrafish embryos

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Pages 203-213 | Received 10 Aug 2023, Accepted 13 Oct 2023, Published online: 24 Oct 2023

References

  • Aebi H. 1984. Catalase in vitro. Methods Enzymol. 105:121–126.
  • Anastas P, Eghbali N. 2010. Green chemistry: principles and practice. Chem Soc Rev. 39(1):301–312. doi: 10.1039/b918763b.
  • Cassiman D, Libbrecht L, Desmet V, Denef C, Roskams T. 2002. Hepatic stellate cell/myofibroblast subpopulations in fibrotic human and rat livers. J Hepatol. 36(2):200–209. doi: 10.1016/s0168-8278(01)00260-4.
  • Dennery PA. 2010. Oxidative stress in development: nature or nurture? Free Radic Biol Med. 49(7):1147–1151. doi: 10.1016/j.freeradbiomed.2010.07.011.
  • Dhakshinamoorthy S, Long DJ, Jaiswal AK. 2000. Antioxidant regulation of genes encoding enzymes that detoxify xenobiotics and carcinogens. Curr Top Cell Regul. 36:201–216.
  • Giussani DA, Salinas CE, Villena M, Blanco CE. 2007. The role of oxygen in prenatal growth: studies in the chick embryo. J Physiol. 585(Pt 3):911–917. doi: 10.1113/jphysiol.2007.141572.
  • Habig WH, Jakoby WB. 1981. Assays for differentiation of glutathione S-transferases. Methods Enzymol. 77:398–405.
  • Hayes JD, Flanagan JU, Jowsey IR. 2005. Glutathione transferases. Annu Rev Pharmacol Toxicol. 45(1):51–88. doi: 10.1146/annurev.pharmtox.45.120403.095857.
  • Joschko MA, Dreosti IE, Tulsi RS. 1993. The teratogenic effects of salicylic acid on the developing nervous system in rats in vitro. Teratology. 48(2):105–114. doi: 10.1002/tera.1420480204.
  • Karabulut AK, Ulger H, Pratten MK. 2000. Protection by free oxygen radical scavenging enzymes against salicylate-induced embryonic malformations in vitro. Toxicol In Vitro. 14(4):297–307. doi: 10.1016/s0887-2333(00)00023-0.
  • Livak KJ, Schmittgen TD. 2001. Analysis of relative gene expression data using real-time quantitative PCR and the 2ΔΔCT method. Methods. 25(4):402–408. doi: 10.1006/meth.2001.1262.
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. 1951. Protein measurement with the Folin phenol reagent. J Biol Chem. 193(1):265–275. doi: 10.1016/S0021-9258(19)52451-6.
  • Miranda KM, Espey MG, Wink DA. 2001. A rapid, simple spectrophotometric method for simultaneous detection of nitrate and nitrite. Nitric Oxide. 5(1):62–71. doi: 10.1006/niox.2000.0319.
  • Morgan TE, Rozovsky I, Goldsmith SK, Stone DJ, Yoshida T, Finch CE. 1997. Increased transcription of the astrocyte gene GFAP during middle-age is attenuated by food restriction: implications for the role of oxidative stress. Free Radic Biol Med. 23(3):524–528. doi: 10.1016/s0891-5849(97)00120-2.
  • Mylroie AA, Collins H, Umbles C, Kyle J. 1986. Erythrocyte superoxide dismutase activity and other parameters of cupper status in rats ingesting lead acetate. Toxicol Appl Pharmacol. 82(3):512–520. doi: 10.1016/0041-008x(86)90286-3.
  • Özokan G, Sağır T, Emekli Alturfan E. 2022. Synthesis of natural salicylic acid as a cosmetic ingredient using green chemistry methods. Experimed. 12(1):12–17. doi: 10.26650/experimed.2022.1068934.
  • Parker D, Martinez C, Stanley C, Simmons J, McIntyre IM. 2004. The analysis of methyl salicylate and salicylic acid from Chinese herbal medicine ingestion. J Anal Toxicol. 28(3):214–216. doi: 10.1093/jat/28.3.214.
  • Putra IB, Jusuf NK, Dewi NK. 2022. Skin changes and safety profile of topical products during pregnancy. J Clin Aesthet Dermatol. 15(2):49–57.
  • Roozifar M, Hazeri N, Faroughi Niya H. 2021. Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives. J Heterocycl Chem. 58(5):1117–1129. doi: 10.1002/jhet.4242.
  • Rossato LG, Costa VM, de Pinho PG, Arbo MD, de Freitas V, Vilain L, Bastos MDL, Palmeira C, Remiao F. 2013. The metabolic profile of mitoxantrone and its relation with mitoxantrone-induced cardiotoxicity. Arch Toxicol. 87(10):1809–1820. doi: 10.1007/s00204-013-1040-6.
  • Saad M, Verbueken E, Pype C, Casteleyn C, Van Ginneken C, Maes L, Cos P, Van Cruchten S. 2016. In vitro CYP1A activity in the zebrafish: temporal but low metabolite levels during organogenesis and lack of gender differences in the adult stage. Reprod Toxicol. 64:50–56. doi: 10.1016/j.reprotox.2016.03.049.
  • Singh G, Sinha N, Sinnollareddy MG. 2009. Role of apoptosis in mediating salicylic acid-induced teratogenesis in vitro. Toxicol Mech Methods. 19(2):161–168. doi: 10.1080/15376510802355349.
  • Vijayaraj P, Le Bras A, Mitchell N, Kondo M, Juliao S, Wasserman M, Beeler D, Spokes K, Aird WC, Baldwin HS, et al. 2012. Erg is a crucial regulator of endocardial–mesenchymal transformation during cardiac valve morphogenesis. Development. 139(21):3973–3985. doi: 10.1242/dev.081596.
  • Warren L. 1959. The thiobarbituric acid assay of sialic acids. J Biol Chem. 234(8):1971–1975.
  • Westerfield M. 1995. The zebrafish book: a guide for the laboratory use of zebrafish (Brachydanio rerio). Eugene (OR): University of Oregon Press.
  • White YA, Kyle JT, Wood AW. 2009. Targeted gene knockdown in zebrafish reveals distinct intraembryonic functions for insulin-like growth factor II signaling. Endocrinology. 150(9):4366–4375. doi: 10.1210/en.2009-0356.
  • Yagi K. 1984. Assay for blood plasma or serum. Methods Enzymol. 105:328–337.

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