Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes
Rong Fu Chen, Yuh Chiang Shen, Hsu Shan Huang, Jyh Fei Liao, Li Kang Ho, Yueh Ching Chou, Wen Yen Wang, Chieh Fu Chen
A variety of anthracene- and anthraquinone-related derivatives, modified from three types of lead structures, including 9-acyloxy 1,5-dichloroanthracene (type I), 1,5-bisacyloxy-anthraquinones with O-linked substituents (type II) and 1,5-bisacyloxy-anthraquinones with S-linked substituents (type III), were synthesized and evaluated by an in-vitro bioassay for their anti-inflammatory and cytotoxic effects in human leucocytes. Among these derivatives, type I compounds displayed potent anti-inflammatory activity against phorbol-12-myristate-13-acetate (PMA)-induced superoxide anion production, a bio-marker of inflammatory mediator production by neutrophils, with 50% inhibition (IC50) concentrations (μM) for compounds 1f, 1g, 1h and 1m being 13.8 ± 3.0, 6.3 ± 4.1, 33.2 ± 1.3 and 33.9 ± 5.7, respectively. Type II and type III derivatives (i.e., 1,5-bisacyloxy anthraquinone-related compounds) and the reference compound, emodin, exhibited relatively minor (20-40%) inhibitory effect against superoxide production by neutrophils. Furthermore, none of these compounds showed a significant cytotoxic effect in human neutrophils. In conclusion, these results suggest that compounds modified from 9-acyloxy 1,5-dichloroanthracence (type I) are more powerful than the other two types as anti-inflammatory drugs. This is the first demonstration that derivatives modified from anthracenes or anthraquinones possess anti-inflammatory activity with no significant cytotoxicity in human neutrophils.
Journal of Pharmacy and Pharmacology
10.1211/0022357023781
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Anthracenes Medicine & Life Sciences 100%
Anticytotoxic Chemical Compounds 83%
Anthraquinones Medicine & Life Sciences 70%
Anthraquinone Chemical Compounds 54%
Antiinflammatory Chemical Compounds 47%
Leukocytes Medicine & Life Sciences 39%
Anti-Inflammatory Agents Medicine & Life Sciences 36%
Neutrophils Medicine & Life Sciences 31%
Chen, R. F., Shen, Y. C., Huang, H. S., Liao, J. F., Ho, L. K., Chou, Y. C., Wang, W. Y., & Chen, C. F. (2004). Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes. Journal of Pharmacy and Pharmacology, 56(7), 915-919. https://doi.org/10.1211/0022357023781
Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes. / Chen, Rong Fu; Shen, Yuh Chiang; Huang, Hsu Shan; Liao, Jyh Fei; Ho, Li Kang; Chou, Yueh Ching; Wang, Wen Yen; Chen, Chieh Fu.
In: Journal of Pharmacy and Pharmacology, Vol. 56, No. 7, 07.2004, p. 915-919.
Chen, RF, Shen, YC, Huang, HS, Liao, JF, Ho, LK, Chou, YC, Wang, WY & Chen, CF 2004, 'Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes', Journal of Pharmacy and Pharmacology, vol. 56, no. 7, pp. 915-919. https://doi.org/10.1211/0022357023781
Chen RF, Shen YC, Huang HS, Liao JF, Ho LK, Chou YC et al. Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes. Journal of Pharmacy and Pharmacology. 2004 Jul;56(7):915-919. https://doi.org/10.1211/0022357023781
Chen, Rong Fu ; Shen, Yuh Chiang ; Huang, Hsu Shan ; Liao, Jyh Fei ; Ho, Li Kang ; Chou, Yueh Ching ; Wang, Wen Yen ; Chen, Chieh Fu. / Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes. In: Journal of Pharmacy and Pharmacology. 2004 ; Vol. 56, No. 7. pp. 915-919.
@article{1419b60c20b640d8b1671bd716bb1322,
title = "Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes",
abstract = "A variety of anthracene- and anthraquinone-related derivatives, modified from three types of lead structures, including 9-acyloxy 1,5-dichloroanthracene (type I), 1,5-bisacyloxy-anthraquinones with O-linked substituents (type II) and 1,5-bisacyloxy-anthraquinones with S-linked substituents (type III), were synthesized and evaluated by an in-vitro bioassay for their anti-inflammatory and cytotoxic effects in human leucocytes. Among these derivatives, type I compounds displayed potent anti-inflammatory activity against phorbol-12-myristate-13-acetate (PMA)-induced superoxide anion production, a bio-marker of inflammatory mediator production by neutrophils, with 50% inhibition (IC50) concentrations (μM) for compounds 1f, 1g, 1h and 1m being 13.8 ± 3.0, 6.3 ± 4.1, 33.2 ± 1.3 and 33.9 ± 5.7, respectively. Type II and type III derivatives (i.e., 1,5-bisacyloxy anthraquinone-related compounds) and the reference compound, emodin, exhibited relatively minor (20-40%) inhibitory effect against superoxide production by neutrophils. Furthermore, none of these compounds showed a significant cytotoxic effect in human neutrophils. In conclusion, these results suggest that compounds modified from 9-acyloxy 1,5-dichloroanthracence (type I) are more powerful than the other two types as anti-inflammatory drugs. This is the first demonstration that derivatives modified from anthracenes or anthraquinones possess anti-inflammatory activity with no significant cytotoxicity in human neutrophils.",
author = "Chen, {Rong Fu} and Shen, {Yuh Chiang} and Huang, {Hsu Shan} and Liao, {Jyh Fei} and Ho, {Li Kang} and Chou, {Yueh Ching} and Wang, {Wen Yen} and Chen, {Chieh Fu}",
journal = "Journal of Pharmacy and Pharmacology",
publisher = "Pharmaceutical Press",
T1 - Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes
AU - Chen, Rong Fu
AU - Shen, Yuh Chiang
AU - Huang, Hsu Shan
AU - Liao, Jyh Fei
AU - Ho, Li Kang
AU - Chou, Yueh Ching
AU - Wang, Wen Yen
AU - Chen, Chieh Fu
N2 - A variety of anthracene- and anthraquinone-related derivatives, modified from three types of lead structures, including 9-acyloxy 1,5-dichloroanthracene (type I), 1,5-bisacyloxy-anthraquinones with O-linked substituents (type II) and 1,5-bisacyloxy-anthraquinones with S-linked substituents (type III), were synthesized and evaluated by an in-vitro bioassay for their anti-inflammatory and cytotoxic effects in human leucocytes. Among these derivatives, type I compounds displayed potent anti-inflammatory activity against phorbol-12-myristate-13-acetate (PMA)-induced superoxide anion production, a bio-marker of inflammatory mediator production by neutrophils, with 50% inhibition (IC50) concentrations (μM) for compounds 1f, 1g, 1h and 1m being 13.8 ± 3.0, 6.3 ± 4.1, 33.2 ± 1.3 and 33.9 ± 5.7, respectively. Type II and type III derivatives (i.e., 1,5-bisacyloxy anthraquinone-related compounds) and the reference compound, emodin, exhibited relatively minor (20-40%) inhibitory effect against superoxide production by neutrophils. Furthermore, none of these compounds showed a significant cytotoxic effect in human neutrophils. In conclusion, these results suggest that compounds modified from 9-acyloxy 1,5-dichloroanthracence (type I) are more powerful than the other two types as anti-inflammatory drugs. This is the first demonstration that derivatives modified from anthracenes or anthraquinones possess anti-inflammatory activity with no significant cytotoxicity in human neutrophils.
AB - A variety of anthracene- and anthraquinone-related derivatives, modified from three types of lead structures, including 9-acyloxy 1,5-dichloroanthracene (type I), 1,5-bisacyloxy-anthraquinones with O-linked substituents (type II) and 1,5-bisacyloxy-anthraquinones with S-linked substituents (type III), were synthesized and evaluated by an in-vitro bioassay for their anti-inflammatory and cytotoxic effects in human leucocytes. Among these derivatives, type I compounds displayed potent anti-inflammatory activity against phorbol-12-myristate-13-acetate (PMA)-induced superoxide anion production, a bio-marker of inflammatory mediator production by neutrophils, with 50% inhibition (IC50) concentrations (μM) for compounds 1f, 1g, 1h and 1m being 13.8 ± 3.0, 6.3 ± 4.1, 33.2 ± 1.3 and 33.9 ± 5.7, respectively. Type II and type III derivatives (i.e., 1,5-bisacyloxy anthraquinone-related compounds) and the reference compound, emodin, exhibited relatively minor (20-40%) inhibitory effect against superoxide production by neutrophils. Furthermore, none of these compounds showed a significant cytotoxic effect in human neutrophils. In conclusion, these results suggest that compounds modified from 9-acyloxy 1,5-dichloroanthracence (type I) are more powerful than the other two types as anti-inflammatory drugs. This is the first demonstration that derivatives modified from anthracenes or anthraquinones possess anti-inflammatory activity with no significant cytotoxicity in human neutrophils.
JO - Journal of Pharmacy and Pharmacology
JF - Journal of Pharmacy and Pharmacology