Synthesis, characterization, and direct aqueous superoxide anion scavenging of a highly water-dispersible astaxanthin-amino acid conjugate

Bioorganic & Medicinal Chemistry Letters
Henry JacksonSamuel F Lockwood

Abstract

The aqueous solubility and/or dispersibility of synthetic carotenoid analogs can be improved by varying the chemical structure(s) of the esterified moieties. In the current study, a highly water-dispersible astaxanthin (3,3'-dihydroxy-beta,beta-carotene-4,4'-dione) derivative was synthesized by esterification to the amino acid L-lysine, and subsequently converted to the tetrahydrochloride salt. Deep violet, evenly colored aqueous suspensions were obtained with addition of the novel derivative to USP purified water up to a maximum of 181.6 mg/mL. These aqueous suspensions were obtained without the addition of heat, detergents, co-solvents, or other additives. At higher concentrations (above 181.6 mg/mL), the dispersion became turbid and viscous. There was no saturation point up to 181.6 mg/mL. The direct superoxide scavenging ability of the tetrahydrochloride dilysine astaxanthin salt was also evaluated by electron paramagnetic resonance (EPR) spectroscopy in a well-characterized in vitro isolated human neutrophil assay. The novel derivative was an extremely potent (micromolar concentration) aqueous-phase scavenger, with near-complete suppression of the superoxide anion signal (as detected by spin-trap adducts of DEPMPO) achieve...Continue Reading

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Citations

Mar 17, 2010·Cell Biology and Toxicology·Anaysa P BolinRosemari Otton
Jul 14, 2005·Molecular and Cellular Biochemistry·Garrett J Gross, Samuel F Lockwood
Jun 15, 2007·Journal of the American Chemical Society·Frederick A VillamenaJay L Zweier
Nov 13, 2010·Journal of the American Chemical Society·Shang-U KimFrederick A Villamena
Dec 5, 2012·Biological & Pharmaceutical Bulletin·Susumu HamaKentaro Kogure
Aug 13, 2010·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Keiko KomagoeTakashi Katsu
Jan 25, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sibel SuzenLuciano Saso
Sep 30, 2004·Bioorganic & Medicinal Chemistry Letters·Ferenc ZsilaSamuel F Lockwood
Mar 28, 2018·Reproduction, Fertility, and Development·J IspadaF F Paula-Lopes
May 2, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Magdolna HádaAttila Agócs
Mar 7, 2007·Chemistry : a European Journal·Hans-Richard SliwkaSamuel F Lockwood
Dec 22, 2009·Physical Chemistry Chemical Physics : PCCP·Annia GalanoAna Martínez
Oct 28, 2005·Cardiovascular Drug Reviews·Samuel F Lockwood, Garrett J Gross
Nov 11, 2019·International Journal of Molecular Sciences·Johant Lakey-BeitiaK S Rao
Mar 12, 2008·The Journal of Organic Chemistry·Yongbin HanFrederick A Villamena
Mar 3, 2020·Journal of Agricultural and Food Chemistry·Yanjun LiuChanghu Xue

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