Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation.
Hsu-Shan Huang
1
,
Jeng-Fong Chiou
2
,
Hui-Fen Chiu
3
,
Jing-Shiang Hwang
4
,
Pen-Yuan Lin
5
,
Chi-Wei Tao
6
,
Pen-Fong Yeh
6
,
Wei-Ren Jeng
1
6
Cheng-Hsin Medical Center
Publication type: Journal Article
Publication date: 2002-11-01
scimago Q3
wos Q3
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
12419916
General Chemistry
Drug Discovery
General Medicine
Abstract
The synthesis of a series of anthraquinone moieties bearing symmetrical sulfur-linked substituents in the 1 and 5 positions is described. These compounds were evaluated for their ability to inhibit the growth of suspended rat glioma C6 cells and human hepatoma G2 cells, respectively. In addition, the redox property of the compounds was determined based on the inhibition of lipid peroxidation in model membranes. Compounds 2a and 2h in this series compared favorably and exhibited the most potent cytotoxicity (0.02, 0.05 microM) against C6 cells in the XTT colorimetric assay. As far as redox properties are concerned, all bis-thio-anthraquinones show potential lipid peroxidation in model membranes very close to that of mitoxantrone (MX), and 2a, 2d, 2e, 2i, 2j, and 2k have more potential than that of MX. The lack of cytotoxicity of compound 2i cannot be related to lipid peroxidation, but the steric and electronic properties of the side-chain substituent maybe impair effective recognition of the cleavable complex. In contrast to MX, 2a and 2h are cytotoxic in rat glioma C6 cells and do not enhance lipid peroxidation in model membranes.
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Citations from 2024:
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Huang H. et al. Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation. // Chemical and Pharmaceutical Bulletin. 2002. Vol. 50. No. 11. pp. 1491-1494.
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Huang H., Chiou J., Chiu H., Hwang J., Lin P., Tao C., Yeh P., Jeng W. Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation. // Chemical and Pharmaceutical Bulletin. 2002. Vol. 50. No. 11. pp. 1491-1494.
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RIS
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TY - JOUR
DO - 10.1248/cpb.50.1491
UR - https://doi.org/10.1248/cpb.50.1491
TI - Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation.
T2 - Chemical and Pharmaceutical Bulletin
AU - Huang, Hsu-Shan
AU - Chiou, Jeng-Fong
AU - Chiu, Hui-Fen
AU - Hwang, Jing-Shiang
AU - Lin, Pen-Yuan
AU - Tao, Chi-Wei
AU - Yeh, Pen-Fong
AU - Jeng, Wei-Ren
PY - 2002
DA - 2002/11/01
PB - Pharmaceutical Society of Japan
SP - 1491-1494
IS - 11
VL - 50
PMID - 12419916
SN - 0009-2363
SN - 1347-5223
ER -
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BibTex (up to 50 authors)
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@article{2002_Huang,
author = {Hsu-Shan Huang and Jeng-Fong Chiou and Hui-Fen Chiu and Jing-Shiang Hwang and Pen-Yuan Lin and Chi-Wei Tao and Pen-Fong Yeh and Wei-Ren Jeng},
title = {Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2002},
volume = {50},
publisher = {Pharmaceutical Society of Japan},
month = {nov},
url = {https://doi.org/10.1248/cpb.50.1491},
number = {11},
pages = {1491--1494},
doi = {10.1248/cpb.50.1491}
}
Cite this
MLA
Copy
Huang, Hsu-Shan, et al. “Synthesis of Symmetrical 1,5-bis-thio-Substituted Anthraquinones for Cytotoxicity in Cultured Tumor Cells and Lipid Peroxidation..” Chemical and Pharmaceutical Bulletin, vol. 50, no. 11, Nov. 2002, pp. 1491-1494. https://doi.org/10.1248/cpb.50.1491.