Synthesis of carotenoid-cysteine conjugates

• Authors: Afshin Zand , Attila Agócs , József Deli , Veronika Nagy
• Languages of publication: EN

Abstracts

EN

Isozeaxanthin under acidic conditions forms an allylic cation which reacts readily with thiol nucleophiles. With N-acetylcysteine as a nucleophile the products obtained are carotenoid-cysteine conjugates in which the amino acid moiety is attached to the carotenoid via sulphur in position 4. The water solubility of the products can be increased by deprotection of the amino group. The antioxidant activity of the products were examined on human liver cells under conditions of hydrogen-peroxide induced oxidative stress.

Keywords

EN

isozeaxanthin; cysteine; cell membrane; oxidative stress

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2012
• Volume: 59
• Issue: 1
• Pages: 149-150

Dates

published

2012

received

2011-10-17

accepted

2012-03-01

(unknown)

2012-03-17

Contributors

author

Afshin Zand

• Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Pécs, Hungary

author

Attila Agócs

• Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Pécs, Hungary

author

József Deli

• Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Pécs, Hungary

author

Veronika Nagy

• Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Pécs, Hungary

References

• Deli J, Agócs A, Iványi R, Németh K, Visy J, Szemán J, Szente L, Simonyi M (2008) Preparation and characterization of water soluble carotenoid/cyclodextrin complexes. Carotenoid Sci 12: 201.
• Háda M, Petrovics D, Nagy V, Böddi K, Deli J, Agócs A (2011) The first synthesis of PEG-carotenoid conjugates. Tetrahedron Lett 52: 3195-3197.
• Lutneas BJ, Kildahl-Andersen G, Krane J, Liaaen-Jensen S (2004) Delocalized carotenoid cations in relation to the soliton model. J Am Chem Soc 126: 8981-8990.
• Nagy V, Agócs A, Turcsi E, Deli J (2010) Experiments on the synthesis of carotenoid glycosides. Tetrahedron Lett 51: 2020-2022.
• Socaciu C, Lausch C, Diehl HA (1999) Carotenoids in DPPC vesicles: membrane dynamics. Spectrochim Acta Part A 55: 2289-2297.
• Tapodi A, Debreceni B, Hantó K, Bognár Z, Wittmann I, Gallyas F, Várbíró G, Sümegi B (2005) Pivotal role of Akt activation in mitochondrial protection and cell survival by poly(ADP-ribose) polymerase-1 inhibition in oxidative stress. J Biol Chem 280: 35767-35775.