在 MRC-5 细胞中，8-羟基喹啉 (8HQ)（化合物 1）表现出细胞毒性，IC50 为 6.27 μM[1]。当与 10.0 μM CuCl2 结合一小时时，8-羟基喹啉 (8-OHQ)（化合物 1）会与铜形成复合物，促进铜转运至人乳腺癌 DCIS 细胞中 [2]。当 8-羟基喹啉与 CuCl2（0–20.0 μM）结合时，它会与铜结合并产生具有酪氨酸激酶抑制剂样活性的复合物（1–5 μM，2–12 小时）[2]。引起 DCIS 细胞的时间和剂量依赖性细胞死亡 [2]。在 Raw 264.7 细胞中，羟基喹啉（0-100 μM，30 分钟）通过激活 NF-κB 并降低 C/EBPb DNA 结合活性来阻断 NO 生成和 iNOS 表达，从而抑制调节因子 [3]。

在 CD1 小鼠中，单次腹腔注射 25-100 mg/kg 剂量的 8-羟基喹啉 (HOQ) 显着增加微核嗜多染红细胞 (MPCE) 的数量 [4]。毛发生长和脱落是由 8-羟基喹啉 (8-HQ)（0.3%，皮肤外观，每周 4 次）引起的，生长模式随着时间的推移而改变 [5]。

细胞活力测定[2]
细胞类型： DCIS 细胞
测试浓度： 1、2.5、5、10、20 μM
孵育时间：1或8小时
实验结果：与铜结合形成复合物，导致细胞聚集和分离，在一定浓度下以时间依赖性方式诱导细胞死亡。 8-OHQ-和CQ-Cu，但不是它们的类似物和Cu混合物，可以以浓度和时间依赖性方式诱导癌细胞死亡。

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蛋白质印迹分析[2]
细胞类型： DCIS 细胞
测试浓度： 1、2.5、5 μM
<孵育持续时间： 0、2、4、8、12 小时
实验结果： CuCl2 混合物在一定浓度和时间下抑制 CT 样活性依赖方式。 CuCl2 混合物以时间依赖性方式降低了蛋白酶体活性并增加了泛素化蛋白和 Bax 的积累。

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RT-PCR[3]
细胞类型：脂多糖刺激的原始 264.7 细胞
测试浓度： 25、50、75、 100 μM
孵育时间： 30 分钟
实验结果： 抑制 LPS 诱导的 NO 和 iNOS 表达。br/> 抑制 iNOS 转录。不影响 MAPK 的磷酸化。抑制 NF-jB 结合活性和 C/EBPb 结合活性。

Animal/Disease Models: CD1 mice[4]
Doses: 25,50,100 mg/kg
Route of Administration: intraperitoneal (ip) injection
Experimental Results: All doses tested resulted in micronucleated polychromatic erythrocytes (MPCE) numbers over a 24-hour sampling period Significant dose-related increase.

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Animal/Disease Models: C57BL mice [5]
Doses: 0.3% Administration 4 times a week: Dermal administration
Experimental Results: Causes depigmented hair to grow in a time-varying manner. Frequent enough use results in nearly complete depigmentation in young adult C57BL female mice, whereas a single application results in isolated bands of depigmented hair.

Absorption, Distribution and Excretion
Oxyquinoline is excreted in both the primarily in the urine with some in the bile.
IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES. MORE 8-HYDROXYQUINOLINE GLUCURONIDE WAS EXCRETED IN URINE THAN 8-HYDROXYQUINOLINE SULFATE CONJUGATE. ONLY THE GLUCURONIDE CONJUGATE WAS EXCRETED IN BILE.
8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. THE GLUCURONIDES WERE EXCRETED IN BILE & URINE, BUT THE SULFATES WERE EXCRETED EXCLUSIVELY IN THE URINE. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

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Metabolism / Metabolites
In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates. In the bile, 9% of the total dose is found as glucuronide conjugates.
IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES.
8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

Toxicity Data
LC50 (rat) > 1,210 mg/m3/6h

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Interactions
AFTER LETHAL IM DOSES IN MICE (30 MG/KG) INJECTED D-PENICILLAMINE (1 G/KG) PREVENTED /TOXIC/ SYMPTOMS & DEATH BUT NOT TRANSIENT HYPERGLYCEMIA.
THE INFLUENCE OF RADIOPROTECTORS, CYSTEAMINE & AMINOETHYLISOTHIOURONIUM AS WELL AS OF THE AMINO ACIDS L-ALANINE, L-CYSTEINE, L-ARGININE, L-ASPARAGINE, L-GLUTAMIC ACID, L-HISTIDINE, & L-METHIONINE, ON THE CYTOGENETIC ACTION OF 8-HYDROXYQUINOLINE SULFATE WAS TESTED IN HUMAN LYMPHOCYTE CULTURES IN VITRO. EXCESS L-CYSTEINE, CYSTEAMINE, & L-ASPARAGINE ADDED SIMULTANEOUSLY WITH 8-HYDROXYQUINOLINE SULFATE DISTINCTLY REDUCED THE CHROMOSOME. DAMAGING EFFECT OF 8-HYDROXYQUINOLINE. L-GLUTAMIC ACID & AMINOETHYLISOTHIOURONIUM EXERTED LESSER PROTECTIVE ACTIVITY. L-METHIONINE DISPLAYED SOME EFFECT ONLY IN REDUCING THE RELATIVELY RARE ISOCHROMATID ABERRATIONS INDUCED BY 8-HYDROXYQUINOLINE SULFATE. THE OTHER AMINO ACIDS HAD NO EFFECT.
The formation of DNA-strand breaks was studied in cultured human lung cells (A 549) subjected to iron, either in the form of iron(III) citrate or in combination with the metal chelators ethylene diamine tetra-acetic acid (EDTA), nitrilo triacetic acid (NTA), or 8-hydroxyquinoline (8HQ). After 15 min exposure to 5 uM iron(III) citrate or iron chelate, the cellular levels of iron were found to be three times higher in cells subjected to iron-8HQ than in cells subjected to iron(III) citrate, iron-EDTA or iron-NTA. Exposure to iron-8HQ caused extensive DNA-strand breakage, whereas no such breakage was found in cells exposed to iron-EDTA or iron-NTA. The DNA damage caused by iron-8HQ increased with time and dose, and DNA-strand breakage was clearly demonstrable in cells after 15 min exposure to as little as 0.1 uM iron-8HQ. Moreover, iron-8HQ was strongly toxic to the cells and inhibited their growth after exposure. Along with the formation of DNA-strand breaks, the concentration of cellular malondialdehyde increased four-fold after exposure to iron-8HQ and two-fold after exposure to iron-EDTA or iron-NTA, suggesting that reactive oxygen metabolites might be involved in the toxic action. Moreover, both iron-EDTA and iron-NTA caused a considerable hydroxylation of deoxyguanosine (dG) residues in DNA in vitro, whereas iron(III) citrate and iron-8HQ only caused a minor hydroxylation of dG. This points to the possibility that iron-8HQ-mediated DNA-strand breakage in cells might be due to the action of a metal-bound oxyl radical formed from the iron-8HQ complex rather than to the formation of hydroxyl radicals. Altogether, these findings indicate that iron bound to the lipophilic chelator, 8HQ, has strong toxic properties and that it may cause substantial DNA-strand breakage and lipid peroxidation in living cells.

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Non-Human Toxicity Values
LD50 Rat oral 1200 mg/kg
LD50 Mice ip 48 mg/kg
LD50 Rat ip 50 mg/kg
LD50 Mouse sc 83,600 ug/kg
For more Non-Human Toxicity Values (Complete) data for 8-HYDROXYQUINOLINE (6 total), please visit the HSDB record page.

[1]. Lawung R, et.al. Repositioning of 8-hydroxyquinoline derivatives as a new promising candidate for combating multidrug resistant Neisseria gonorrhoeae. EXCLI J. 2018 Aug 23;17:840-846.
[2]. 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells. J Biol Inorg Chem. 2010 Feb;15(2):259-69.
[3]. Zhai S, et.al. Tumor cellular proteasome inhibition and growth suppression by
[4]. Hamoud MA, et.al. Effects of quinoline and 8-hydroxyquinoline on mouse bone marrow erythrocytes as measured by the micronucleus assay. Teratog Carcinog Mutagen. 1989;9(2):111-8.
[5]. Searle CE. The selective depigmenting action of 8-hydroxyquinoline on hair growth in the mouse. Br J Dermatol. 1972 May;86(5):472-80.

8-hydroxyquinoline appears as white to off-white or faintly yellow crystalline powder. Phenolic odor. (NTP, 1992)
Quinolin-8-ol is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes. It has a role as an antibacterial agent, an iron chelator, an antiseptic drug and an antifungal agrochemical. It derives from a hydride of a quinoline.
Oxyquinoline is a heterocyclic phenol and derivative of quinoline with antiseptic, disinfectant, and pesticide properties. It is used as a stabilizer for hydrogen peroxide, where it is sometimes added in cosmetic products.
8-Hydroxyquinoline has been reported in Cortinarius subtortus and Allium stipitatum with data available.
An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.
See also: Acetic acid; oxyquinoline (component of).

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Drug Indication
Oxyquinoline is used as a biocidal component of several over the counter products. These products are marketed for the purposes of inhibiting abnormal biological growth in the vagina and restoring natural pH.

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Mechanism of Action
The mechanism by which oxyquinoline exerts its biocidal effect is unknown.

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Therapeutic Uses
A BACTERIOSTATIC & FUNGISTATIC COMPOUND; USED PRINCIPALLY IN TREATMENT OF MINOR BURNS & OF HEMORRHOIDS.
OXYQUINOLINE SULFATE ... IS ... USED ... IN TREATMENT OF ATHLETE'S FOOT, VAGINITIS, & AS A GARGLE, EYEWASH, NASAL DOUCHE, & IN HEMORRHOIDAL PREPARATIONS ... /OXYQUINOLINE SULFATE/
/OVER THE COUNTER/ HYDROXYQUINOLINE IS 1 OF 4 ANTIFUNGAL AGENTS RECOMMENDED FOR ACTIVE TREATMENT OF FUNGUS ASSOCIATED WITH DIAPER RASH & PRICKLY HEAT IN BABIES. /HYDROXYQUINOLINE/
8-HYDROXYQUNIOLINE SULFATE INHIBITED FORMATION OF ARTIFICIAL CALCULUS IN VITRO & RAT CALCULUS IN VIVO. IN RATS, IT PREVENTED CALCULUS FORMATION WHEN APPLIED BY SWABBING OR BY INTRAORAL INSTILLATION. IN DOGS, FORMATION OF DENTAL PLAQUE WAS INHIBITED 33 TO 98% IN COMPARISON TO PLACEBO. ALSO, 25 TO 58% OF ESTABLISHED PLAQUE ACCUMULATIONS WERE REMOVED, WHEREAS PLACEBO REMOVED 2 TO 22%.
For more Therapeutic Uses (Complete) data for 8-HYDROXYQUINOLINE (7 total), please visit the HSDB record page.

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Pharmacodynamics
Oxyquinoline acts as a biocide to eliminate bacteria and fungi.

C9H7O

145.16

145.052

148-24-3

8-Hydroxyquinoline hemisulfate;134-31-6

1923

White crystals or white crystalline powder

1.3±0.1 g/cm3

267.0±0.0 °C at 760 mmHg

70-73 °C(lit.)

143.1±20.4 °C

0.0±0.5 mmHg at 25°C

1.691

1.87

33.12

1

2

0

11

138

0

O([H])C1=C([H])C([H])=C([H])C2C([H])=C([H])C([H])=NC=21

MCJGNVYPOGVAJF-UHFFFAOYSA-N

InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

quinolin-8-ol

NSC-2039; NSC 2039; Oxyquinoline

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~50 mg/mL (~344.45 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (17.22 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入到400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.5 mg/mL (17.22 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 2.5 mg/mL (17.22 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。