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Acridine Sale

(Synonyms: 吖啶) 目录号 : GC49804

An azaarene

Acridine Chemical Structure

Cas No.:260-94-6

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5 g
¥619.00
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10 g
¥1,174.00
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25 g
¥2,474.00
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50 g
¥4,647.00
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产品描述

Acridine is an azaarene.1 It is a scaffold component of many pharmacologically active compounds, including topoisomerase inhibitors and DNA intercalators, as well as compounds with anticancer and antimalarial activities.2,3,4,5 Acridine is also the backbone of some fluorescent probes, such as acridine orange and ICAAc .6,7 It is genotoxic to bacteria when used at a concentration of 50 µg/ml.1

1.Skarek, M., Cupr, P., RÉblova, K., et al.Assessment of toxic and genotoxic effects of N-heterocyclic polyaromatic hydrocarbons with miniaturized in vitro screening bioassays1-4() 2.Nelson, E.M., Tewey, K.M., and Liu, L.F.Mechanism of antitumor drug action: Poisoning of mammalian DNA topoisomerase II on DNA by 4’-(9-acridinylamino)-methanesulfon-m-anisidideProc. Natl. Acad. Sci. USA81(5)1361-1365(1984) 3.Fukui, K., Tanaka, K., Fujitsuka, M., et al.Distance dpendence of electron transfer in acridine-intercalated DNAJ. Photochem. Photobiol. B Biol.5018-27(1999) 4.Heald, R.A., Modi, C., Cookson, J.C., et al.Antitumor polycyclic acridines. 8.1 Synthesis and telomerase-inhibitory activity of methylated pentacyclic acridinium saltsJ. Med. Chem.45(3)590-597(2002) 5.Kumar, R., Kaur, M., and Kumari, M.Acridine: A versatile heterocyclic nucleusActa Pol. Pharm.69(1)3-9(2012) 6.Han, J., and Burgess, K.Fluorescent indicators for intracellular pHChem. Revs.110(5)2709-2728(2010) 7.Nagy, M., Racz, D., Nagy, Z.L., et al.Amino-isocyanoacridines: Novel, tunable solvatochromic fluorophores as phystiological pH probesSci. Rep.98250(2019)

Chemical Properties

Cas No. 260-94-6 SDF Download SDF
别名 吖啶
Canonical SMILES C1(N=C2C=CC=CC2=C3)=C3C=CC=C1
分子式 C13H9N 分子量 179.2
溶解度 DMF: 2 mg/ml,DMSO: 10 mg/ml,Ethanol: 10 mg/ml,PBS (pH 7.2): insol 储存条件 -20°C
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1 mM 5.5804 mL 27.9018 mL 55.8036 mL
5 mM 1.1161 mL 5.5804 mL 11.1607 mL
10 mM 0.558 mL 2.7902 mL 5.5804 mL
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Research Update

Acridine as an Anti-Tumour Agent: A Critical Review

Molecules 2022 Dec 26;28(1):193.PMID:36615391DOI:10.3390/molecules28010193.

This review summarized the current breakthroughs in the chemistry of acridines as anti-cancer agents, including new structural and biologically active Acridine attributes. Acridine derivatives are a class of compounds that are being extensively researched as potential anti-cancer drugs. Acridines are well-known for their high cytotoxic activity; however, their clinical application is restricted or even excluded as a result of side effects. The photocytotoxicity of propyl Acridine acts against leukaemia cell lines, with C1748 being a promising anti-tumour drug against UDP-UGT's. CK0403 is reported in breast cancer treatment and is more potent than CK0402 against estrogen receptor-negative HER2. Acridine platinum (Pt) complexes have shown specificity on the evaluated DNA sequences; 9-anilinoacridine core, which intercalates DNA, and a methyl triazene DNA-methylating moiety were also studied. Acridine thiourea gold and acridinone derivatives act against cell lines such as MDA-MB-231, SK-BR-3, and MCF-7. Benzimidazole Acridine compounds demonstrated cytotoxic activity against Dual Topo and PARP-1. Quinacrine, thiazacridine, and azacridine are reported as anti-cancer agents, which have been reported in the previous decade and were addressed in this review article.

Acridine derivatives as inhibitors/poisons of topoisomerase II

J Appl Toxicol 2022 Apr;42(4):544-552.PMID:34514603DOI:10.1002/jat.4238.

The potential of acridines (amsacrine) as a topoisomerase II inhibitor or poison was first discovered in 1984, and since then, a considerable number of Acridine derivatives have been tested as topoisomerase inhibitors/poisons, containing different substituents on the Acridine chromophore. This review will discuss a series of studies published over the course of the last decade, which have investigated various novel Acridine derivatives against topoisomerase II activity.

Current Scenario of Acridine Hybrids with Anticancer Potential

Curr Top Med Chem 2021;21(19):1773-1786.PMID:34348622DOI:10.2174/1568026621666210804115203.

Cancer, a complex disease which involves abnormalities of multiple cellular pathways, is one of the most serious threatens to human health across the world. Chemotherapy with a single agent or a combined regimen is a standardized strategy for the treatment of almost all human cancers, and the cure rate of cancer increases with the continuous discovery of anticancer agents and the optimization of chemotherapy options. However, drug resistance, especially multidrug resistance, remains an obstacle in the effective treatment of cancer. Hence, it is urgent to develop novel agents with potential activity against cancers, especially drug-resistant forms. Acridine, which bears three fused rings, could intercalate into DNA and interfere with metabolic processes. Recently, acridines have been found with anticancer activity in a variety of malignancies through suppressing cell proliferation, stimulating apoptosis, and inducing cell cycle arrest, retarding migration, invasion and metastasis. Thus, acridines are useful scaffolds for the discovery of novel drug candidates with potent anticancer activity. This review focused on the current scenario of Acridine hybrids with potential activity against cancers reported from Jan, 2015 to Feb, 2021. The mechanisms of action, the criteria of compound design as well as structure-activity relationships were also summarized to pave the way for a further rational design of novel anticancer agents.

Acriflavine, an Acridine Derivative for Biomedical Application: Current State of the Art

J Med Chem 2022 Sep 8;65(17):11415-11432.PMID:36018000DOI:10.1021/acs.jmedchem.2c00573.

Acriflavine (ACF) has been known for years as an antibacterial drug. The identification of key oncogenic mechanisms has brought, in recent years, a significant increase in studies on ACF as a multipurpose drug that would improve the prognosis for cancer patients. ACF interferes with the expression of the hypoxia inducible factor, thus acting on metastatic niches of tumors and significantly enhancing the effects of other anticancer therapies. It has been recognized as the most potent HIF-1 inhibitor out of the 336 drugs approved by the FDA. This work presents up-to-date knowledge about the mechanisms of action of ACF and its related prodrug systems in the context of anticancer and SARS-CoV-2 inhibitory properties. It explains the multitask nature of this drug and suggests mechanisms of ACF's action on the coronavirus. Other recent reports on ACF-based systems as potential antibacterial and antiviral drugs are also described.

Acridine: a versatile heterocyclic nucleus

Acta Pol Pharm 2012 Jan-Feb;69(1):3-9.PMID:22574501doi

Acridine is a heterocyclic nucleus. It plays an important role in various medicines. A number of therapeutic agents are based on Acridine nucleus such as quinacrine (antimalarial), acriflavine and proflavine (antiseptics), ethacridine (abortifacient), amsacrine and nitracine (anticancer), and tacrine. Acridine is obtained from high boiling fraction of coal tar. It is also obtained in nature from plant and marine sources. Acridine undergoes a number of reactions such as nucleophilic addition, electrophilic substitution, oxidation, reduction, reductive alkylation and photoalkylation. The present review article summarizes the synthesis, reaction, literature review and pharmaceutical importance of Acridine.