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1-Hydroxyanthraquinone Sale

(Synonyms: 1-羟基蒽醌) 目录号 : GC48909

An anthraquinone with genotoxic and carcinogenic activities

1-Hydroxyanthraquinone Chemical Structure

Cas No.:129-43-1

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产品描述

1-Hydroxyanthraquinone is an anthraquinone that has been found in Morinda officinalis and has genotoxic and carcinogenic activities.1,2 1-Hydroxyanthraquinone (5 and 500 µM) increases the percentage of isolated rat hepatocytes undergoing unscheduled DNA synthesis, indicating genotoxic activity.1 Dietary administration of 1-hydroxyanthraquinone (1%) induces formation of cecum and colon adenocarcinomas, as well as hepatocellular carcinomas, in rats.

1.Kawai, K., Mori, H., Sugie, S., et al.Genotoxicity in the hepatocyte/DNA repair test and toxicity to liver mitochondria of 1-hydroxyanthraquinone and several dihydroxyanthraquinonesCell Biol. Toxicol.2(4)457-467(1986) 2.Mori, H., Yoshimi, N., Iwata, H., et al.Carcinogenicity of naturally occurring 1-hydroxyanthraquinone in rats: Induction of large bowel, liver and stomach neoplasmsCarcinogenesis11(5)799-802(1990)

Chemical Properties

Cas No. 129-43-1 SDF
别名 1-羟基蒽醌
Canonical SMILES O=C1C2=C(C(C3=C1C=CC=C3O)=O)C=CC=C2
分子式 C14H8O3 分子量 224.2
溶解度 Chloroform: 30 mg/ml 储存条件 -20°C
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1 mM 4.4603 mL 22.3015 mL 44.603 mL
5 mM 0.8921 mL 4.4603 mL 8.9206 mL
10 mM 0.446 mL 2.2302 mL 4.4603 mL
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Research Update

1-Hydroxyanthraquinone exhibited antibacterial activity by regulating glutamine synthetase of Staphylococcus xylosus as a virulence factor

Biomed Pharmacother 2020 Mar;123:109779.PMID:31918211DOI:10.1016/j.biopha.2019.109779.

Staphylococcus xylosus (S. xylosus) is one of the emerging pathogens causing bovine mastitis with high rate of isolation in most of the reported clinical and field cases. To verify the role of glutamine synthetase (GS) in the pathogenesis of S. xylosus, we evaluated the virulence level of the wild-type strain and its glnA mutant strain in biofilm assays in vitro and murine infection model in vivo. From the results, it was observed that the glnA mutant strain was attenuated and could reduce tissue damage. 1-Hydroxyanthraquinone (1-HAQ) is a kind of anthraquinones, it exhibited a significant inhibitory effect on the growth of S. xylosus and biofilm formation in vitro and provided anti-inflammatory effects in vivo. In addition, the rate at which it inhibits the biofilm, inflammatory factors, and CFU of wild-type strains were significantly higher than that of the mutant strains, indicating that 1-hAQ might have pharmacological effects against S. xylosus through the regulation of GS protein. The effect of 1-hAQ on GS was further confirmed by the down-regulation of glnA expression, reduced GS activity, Gln content and the results of molecular docking. Taken together, these findings suggest that 1-hAQ facilitated a significant attenuation of S. xylosus pathogenicity by regulating the GS protein: a vital virulence factor. Therefore, it can be inferred that 1-hAQ may serve as a potential source of organic compound for the development of novel alternative drugs in mitigating the menace of bovine mastitis.

Novel 18F-Labeled 1-Hydroxyanthraquinone Derivatives for Necrotic Myocardium Imaging

ACS Med Chem Lett 2016 Dec 28;8(2):191-195.PMID:28197310DOI:10.1021/acsmedchemlett.6b00398.

Rapid detection and precise evaluation of myocardial viability is necessary to aid in clinical decision making whether to recommend revascularization for patients with myocardial infarction (MI). Three novel 18F-labeled 1-Hydroxyanthraquinone derivatives were synthesized, characterized, and evaluated as potential necrosis avid imaging agents for assessment of myocardial viability. Among these tracers, [18F]FA3OP emerged as the most promising compound with best stability and highest targetability. Clear PET images of [18F]FA3OP were obtained in rat model of myocardial infarction and reperfusion at 1 h after injection. In addition, the possible mechanisms of [18F]FA3OP for necrotic myocardium were discussed. The results showed [19F]FA3OP may bind DNA to achieve targetability to necrotic myocardium by intercalation. In summary, [18F]FA3OP was a more promising "hot spot imaging" tracer for rapid visualization of necrotic myocardium.

Expression of cytokines, TNF-alpha and IL-1 alpha, in MAM acetate and 1-hydroxyanthraquinone-induced colon carcinogenesis of rats

Carcinogenesis 1994 Apr;15(4):783-5.PMID:8149497DOI:10.1093/carcin/15.4.783.

The expression of cytokines, TNF-alpha and IL-1 alpha, was examined by means of a reverse transcription followed by PCR (RT-PCR) in rat colon carcinogenesis. Forty male F344 rats were used and divided into four groups. At the start of the experiment, 20 rats were treated with methylazoxymethanol (MAM) acetate (25 mg/kg body wt, one time, i.p.) and divided into two groups; group 1 was exposed to 1% 1-Hydroxyanthraquinone (1-HAQ) and group 2 was fed a basal diet during the experiment (40 weeks). Other rats were also divided into two groups; group 3 was exposed to 1% 1-HAQ as group 1, and group 4 was used as control. Tumor incidence (100%) and multiplicity (5.00 +/- 2.05) in group 1 were significantly greater than those in group 2 (20% and 0.2 +/- 0.42) and group 3 (10% and 0.10 +/- 0.32) (P < 0.01 and P < 0.01 respectively). RT-PCR technique with RNA was applied to the tissues from colon neoplasms and mucosa in each group. Expression of TNF-alpha and IL-1 alpha in the colon neoplasms was much stronger than that in the colon mucosa of each group (P < 0.001 and P < 0.01 respectively). The expression of TNF-alpha was more remarkable in the colon mucosa of group 1 than that in corresponding tissue of groups 2 and 3 (P < 0.01). The expressions of TNF-alpha and IL-1 alpha were more increased in the colon mucosa of groups 1, 2 and 3 than that in group 4 as control (P < 0.01 and P < 0.05 respectively). The results indicate that TNF-alpha and IL-1 alpha may act as growth factors in rat colon carcinogenesis by MAM acetate and 1-HAQ. In addition, the synergistic effect of 1-HAQ with MAM acetate in colon carcinogenesis might be related to biological effects of the cytokines expressed in the inflammatory condition generated by 1-HAQ.

The synergistic effect of 1-Hydroxyanthraquinone on methylazoxymethanol acetate-induced carcinogenesis in rats

Carcinogenesis 1991 Feb;12(2):335-8.PMID:1847322DOI:10.1093/carcin/12.2.335.

The synergistic potential of 1-Hydroxyanthraquinone (1-HA) on methylazoxymethanol (MAM) acetate-induced carcinogenesis was investigated in rats. A total of 154 inbred ACI/N rats (73 males and 81 females), six weeks old at the start of the experiment, were divided into four groups: group 1 was given i.p. injections of MAM acetate (25 mg/kg body wt), once per week for 2 weeks and then fed the diet containing 1% 1-HA for 42 weeks; group 2 received MAM acetate and was kept on the basal diet alone; group 3 was given 1-HA containing diet alone as for group 1; group 4 was treated as a control. At the termination of the experiment, the carcinogenic effect of MAM acetate and 1-HA in the large bowel or liver exceeded the sum of effects when given alone, indicating that the two chemicals act synergistically in the carcinogenesis of these organs.

Carcinogenicity of naturally occurring 1-Hydroxyanthraquinone in rats: induction of large bowel, liver and stomach neoplasms

Carcinogenesis 1990 May;11(5):799-802.PMID:2335008DOI:10.1093/carcin/11.5.799.

The carcinogenic potential of 1-Hydroxyanthraquinone (HA), a naturally occurring compound, was examined. A total of 60 male ACI/N rats, 1.5 months old at the commencement were divided into two groups. Group 1 (30 rats) were fed the diet containing HA at a concentration of 1% throughout the experiment (480 days). Group 2 (30 rats) served as the control given a basal diet alone. Twenty-five of 29 effective animals in group 1 developed adenomas or adenocarcinomas in the cecum or upper portion of the colon, the mean number of large bowel tumors/tumor bearing rat being 2.3. In addition to these intestinal tumors, liver neoplasms (neoplastic nodules and hepatocellular carcinomas) were observed in 12 rats and benign stomach tumors were obtained in five animals; no rats of group 2 demonstrating development of any of these tumor types. The incidences of the large bowel, liver and stomach neoplasms in group 1 were all significant as compared with group 2 (P less than 2 x 10(-13), P less than 5 x 10(-5) and P less than 3 x 10(-2) respectively) clearly indicating that HA is carcinogenic in rats.