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Merck
CN

L2037

β-拉帕康

synthetic (organic), ≥98% (TLC), DNA topoisomerase typeI inhibitor, powder

别名:

ARQ 501, NSC 26326, NSC 629749, SL 11001

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关于此项目

经验公式(希尔记法):
C15H14O3
化学文摘社编号:
分子量:
242.27
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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产品名称

β-拉帕康, ≥98% (TLC)

SMILES string

CC1(C)CCC2=C(O1)c3ccccc3C(=O)C2=O

InChI

1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

InChI key

QZPQTZZNNJUOLS-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

Quality Level

Application

ββ-拉帕醌已用于:
  • 作为抗癌药物,用于Lewis肺癌(LLC)细胞和已分离线粒体的过氧化氢酶抑制型鲁米诺/过氧化氢(HRP)-依赖性化学发光检测
  • 作为萘醌类物质,研究其对小鼠粒细胞和巨噬细胞祖细胞生长和分化的影响
  • 作为人重组NAD(P)H脱氢酶1(NQO1)酶活研究底物

Biochem/physiol Actions

β-Lapachone 是一种天然存在的醌,从具有癌症化学预防属性的重蚁木树 (Tabebuia avellanedae) 的树皮中获得。诱导 HL-60 和人前列腺癌细胞凋亡。
β-拉帕醌主要用作I型DNA拓扑异构酶抑制剂,具有抗真菌、抗细菌、杀锥虫和抗病毒活性。β-拉帕醌也可抑制肺泡巨噬细胞诱导型一氧化氮合酶(iNOS)活性和一氧化氮(NO)生成。

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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David Siegel et al.
Biochemical pharmacology, 83(8), 1033-1040 (2012-01-03)
Quinones represent a large and diverse class of antitumor drugs and many quinones are approved for clinical use or are currently undergoing evaluation in clinical trials. For many quinones reduction to the hydroquinone has been shown to play a key
S M Wuerzberger et al.
Cancer research, 58(9), 1876-1885 (1998-05-15)
Beta-lapachone (beta-lap) affects a number of enzymes in vitro, including type I topoisomerase (Topo I); however, its exact intracellular target(s) and mechanism of cell killing remain unknown. We compared the cytotoxic responses of MCF-7:WS8 (MCF-7) human breast cancer cells after
C J Li et al.
The Journal of biological chemistry, 268(30), 22463-22468 (1993-10-25)
beta-Lapachone is a plant product that has been found to have many pharmacological effects. To date, very little is known about its biochemical target. In this study, we found that beta-lapachone inhibits the catalytic activity of topoisomerase I from calf
Xiumei Huang et al.
Cancer research, 72(12), 3038-3047 (2012-04-26)
Agents, such as β-lapachone, that target the redox enzyme, NAD(P)H:quinone oxidoreductase 1 (NQO1), to induce programmed necrosis in solid tumors have shown great promise, but more potent tumor-selective compounds are needed. Here, we report that deoxynyboquinone kills a wide spectrum
Oliver Quevedo et al.
Chemical research in toxicology, 24(12), 2106-2108 (2011-11-19)
β-Lapachone (β-lap) is a promising antitumoral agent. DNA base oxidation and alkylation are among the expected damages by β-lap. Herein, we have explored the role that the homologous recombination pathway (HR), a critical DNA repair process in Saccharomyces cerevisiae, has

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