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Potential Antitumor Activity of 2-O-α-d-Glucopyranosyl-6-O-(2-Pentylheptanoyl)-l-Ascorbic Acid

1
Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, 5562 Nanatsuka-cho, Shobara, Hiroshima 727-0023, Japan
2
Faculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2018, 19(2), 535; https://doi.org/10.3390/ijms19020535
Received: 18 January 2018 / Revised: 30 January 2018 / Accepted: 6 February 2018 / Published: 10 February 2018
(This article belongs to the Section Bioactives and Nutraceuticals)
Intravenous administration of high-dose ascorbic acid (AA) has been reported as a treatment for cancer patients. However, cancer patients with renal failure cannot receive this therapy because high-dose AA infusion can have side effects. To solve this problem, we evaluated the antitumor activity of a lipophilic stable AA derivative, 2-O-α-d-glucopyranosyl-6-O-(2-pentylheptanoyl)-l-ascorbic acid (6-bOcta-AA-2G). Intravenous administration of 6-bOcta-AA-2G suppressed tumor growth in colon-26 tumor-bearing mice more strongly than did AA, even at 1/10 of the molar amount of AA. Experiments on the biodistribution and clearance of 6-bOcta-AA-2G and its metabolites in tumor-bearing mice showed that 6-bOcta-AA-2G was hydrolyzed to 6-O-(2-propylpentanoyl)-l-ascorbic acid (6-bOcta-AA) slowly to yield AA, and the results suggested that this characteristic metabolic pattern is responsible for making the antitumor activity of 6-bOcta-AA-2G stronger than that of AA and that the active form of 6-bOcta-AA-2G showing antitumor activity is 6-bOcta-AA. In in vitro experiments, the oxidized form of 6-bOcta-AA as well as 6-bOcta-AA showed significant cytotoxicity, while the oxidized forms of ascorbic acid showed no cytotoxicity at all, suggesting that the antitumor activity mechanism of 6-bOcta-AA-2G is different from that of AA and that the antitumor activity is due to the reduced and oxidized form of 6-bOcta-AA. The findings suggest that 6-bOcta-AA-2G is a potent candidate as an alternative drug to intravenous high-dose AA. View Full-Text
Keywords: ascorbic acid; stable ascorbic acid derivatives; acyl ascorbic acid; antitumor activity ascorbic acid; stable ascorbic acid derivatives; acyl ascorbic acid; antitumor activity
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MDPI and ACS Style

Miura, K.; Haraguchi, M.; Ito, H.; Tai, A. Potential Antitumor Activity of 2-O-α-d-Glucopyranosyl-6-O-(2-Pentylheptanoyl)-l-Ascorbic Acid. Int. J. Mol. Sci. 2018, 19, 535. https://doi.org/10.3390/ijms19020535

AMA Style

Miura K, Haraguchi M, Ito H, Tai A. Potential Antitumor Activity of 2-O-α-d-Glucopyranosyl-6-O-(2-Pentylheptanoyl)-l-Ascorbic Acid. International Journal of Molecular Sciences. 2018; 19(2):535. https://doi.org/10.3390/ijms19020535

Chicago/Turabian Style

Miura, Kaori; Haraguchi, Misaki; Ito, Hideyuki; Tai, Akihiro. 2018. "Potential Antitumor Activity of 2-O-α-d-Glucopyranosyl-6-O-(2-Pentylheptanoyl)-l-Ascorbic Acid" Int. J. Mol. Sci. 19, no. 2: 535. https://doi.org/10.3390/ijms19020535

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