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Carcinogenesis Advance Access originally published online on May 11, 2005
Carcinogenesis 2005 26(9):1634-1641; doi:10.1093/carcin/bgi121
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Carcinogenesis vol.26 no.9 © Oxford University Press 2005; all rights reserved.

Inhibition of chemically-induced neoplastic transformation by a novel tetrasodium diphosphate astaxanthin derivative

Laura M. Hix 1, 2, 5, Dean A. Frey 3, Mark D. McLaws 3, Marianne Østerlie 4, Samuel F. Lockwood 2 and John S. Bertram 5, 6, *

1 Department of Cell and Molecular Biology, University of Hawaii at Manoa, Honolulu, HI 96822, USA, 2 Hawaii Biotech, Inc., Aiea, HI 96701, USA, 3 Chemical Development and Analytical Quality Services, Albany Molecular Research Inc., Albany, NY 12212, USA, 4 HIST, Department of Food Science, N-7004, Trondheim, Norway and 5 Cancer Research Center of Hawaii, University of Hawaii at Manoa, Honolulu, HI 96813, USA

* To whom correspondence should be addressed. Tel: +1 808 586 2957; Fax: +1 808 586 2984; Email: john{at}crch.hawaii.edu

Carotenoids have been implicated in numerous epidemiological studies as being protective against cancer at many sites, and their chemopreventive properties have been confirmed in laboratory studies. Astaxanthin (AST), primarily a carotenoid of marine origin, responsible for the pink coloration of salmon, shrimp and lobster, has received relatively little attention. As with other carotenoids, its highly lipophilic properties complicate delivery to model systems. To overcome this issue we have synthesized a novel tetrasodium diphosphate astaxanthin (pAST) derivative with aqueous dispersibility of 25.21 mg/ml. pAST was delivered to C3H/10T1/2 cells in an aqueous/ethanol solution and compared with non-esterified AST dissolved in tetrahydrofuran. We show pAST to (i) upregulate connexin 43 (Cx43) protein expression; (ii) increase the formation of Cx43 immunoreactive plaques; (iii) upregulate gap junctional intercellular communication (GJIC); and (iv) cause 100% inhibition of methylcholanthrene-induced neoplastic transformation at 10–6 M. In all these assays, pAST was superior to non-esterified AST itself; in fact, pAST exceeded the potency of all other previously tested carotenoids in this model system. Cleavage of pAST to non-esterified (free) AST and uptake into cells was also verified by HPLC; however, levels of free AST were ~100-fold lower than in cells treated with AST itself, suggesting that pAST possesses intrinsic activity. The dual properties of water dispersibility (enabling parenteral administration in vivo) and increased potency should prove extremely useful in the future development of cancer chemopreventive agents.


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F. Daubrawa, H. Sies, and W. Stahl
Astaxanthin Diminishes Gap Junctional Intercellular Communication in Primary Human Fibroblasts
J. Nutr., November 1, 2005; 135(11): 2507 - 2511.
[Abstract] [Full Text] [PDF]


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