2-Aminoimidazole
(Synonyms: 2-氨基咪唑) 目录号 : GC61639
2-Aminoimidazole是一种有效的抗生物膜剂，可用作抗菌佐剂。2-Aminoimidazole通过抑制生物被膜的形成和基因编码的抗生素抗性特征来破坏细菌自我保护的能力。2-Aminoimidazole也是一种弱的非竞争性人精氨酸酶I(humanarginaseI)抑制剂，Ki值为3.6mM。
Cas No.:7720-39-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Aminoimidazole is a potent antibiofilm agent that can be used as an adjuvant to antimicrobial. 2-aminoimidazoles disrupts the ability of bacteria to protect themselves by inhibiting biofilm formation and genetically-encoded antibiotic resistance traits. 2-Aminoimidazole is also a weak noncompetitive inhibitor of human arginase I with a Ki of 3.6 mM[1][2][3].
[1]. Thompson RJ, et, al. Identification of BfmR, a response regulator involved in biofilm development, as a target for a 2-Aminoimidazole-based antibiofilm agent. Biochemistry. 2012 Dec 11;51(49):9776-8. [2]. Jacobs L, et, al. 2-Aminoimidazoles as potent inhibitors of contaminating brewery biofilms. Biofouling. 2021 Feb 11;1-17. [3]. Ilies M, et, al. 2-aminoimidazole amino acids as inhibitors of the binuclear manganese metalloenzyme human arginase I. J Med Chem. 2010 May 27;53(10):4266-76.
| Cas No. | 7720-39-0 | SDF | |
| 别名 | 2-氨基咪唑 | ||
| Canonical SMILES | NC1=NC=CN1 | ||
| 分子式 | C3H5N3 | 分子量 | 83.09 |
| 溶解度 | 储存条件 | 4°C, protect from light | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 12.0351 mL | 60.1757 mL | 120.3514 mL |
| 5 mM | 2.407 mL | 12.0351 mL | 24.0703 mL |
| 10 mM | 1.2035 mL | 6.0176 mL | 12.0351 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
2-Aminoimidazole Reduces Fouling and Improves Membrane Performance
J Memb Sci 2021 Jul 1;629:119262.PMID:34366551DOI:10.1016/j.memsci.2021.119262.
Biofouling is difficult to control and hinders the performance of membranes in all applications but is of particular concern when natural waters are purified. Fouling, via multiple mechanisms (organic-only, biofouling-only, cell-deposition-only, and organic+biofouling), of a commercially available membrane (control) and a corresponding membrane coated with an anti-biofouling 2-Aminoimidazole (2-AI membrane) was monitored and characterized during the purification of a natural water. Results show that the amount of bacterial cell deposition and organic fouling was not significantly different between control and 2-AI membranes; however, biofilm formation, concurrent or not with other fouling mechanisms, was significantly inhibited (95-98%, p<0.001) by the 2-AI membrane. The limited biofilm that formed on the 2-AI membrane was weaker (as indicated by the polysaccharide to protein ratio) and thus presumably easier to remove. The conductivity rejection by the 2-AI and control membranes was not significantly different throughout the 75-hour experiments, but the rejection of dissolved organic carbon by biofouled (biofouling-only, cell-deposition-only, and organic+biofouling) 2-AI membranes was statistically higher (10-12%, p=0.003-0.07). When biofouled, the water permeance of the 2-AI membranes decreased significantly less (p<0.05) over 75 hours than that of the control membranes, whether or not other additional types of fouling occurred concurrently. Despite the initially lower water permeances of 2-AI membranes (11% lower on average than controls), the 2-AI membranes outperformed the controls (10-11% higher average water permeance) after biofilm formation occurred. Overall, 2-AI membranes fouled less than controls without detriment to water productivity and solute rejection.
2-Aminoimidazole, glycociamidine and 2-thiohydantoin-marine alkaloids as molecular inspirations for the development of lead structures
Curr Drug Targets 2011 Oct;12(11):1689-708.PMID:21561428DOI:10.2174/138945011798109428.
This review provides a detailed account on the biological activities of structurally diverse secondary metabolites from marine sponges having 2-Aminoimidazole, glycociamidine and/or 2-thiohydantoin ring functions. This review will complement two previous short reviews which did however not address the potential of these natural products for drug discovery. We will discuss the naturally occurring alkaloids and give an account on their structure activity relationships.
2-Aminoimidazole Analogs Target PhoP Altering DNA Binding Activity and Affect Outer Membrane Stability in Gram-Negative Bacteria
Biochemistry 2022 Dec 20;61(24):2948-2960.PMID:36454711DOI:10.1021/acs.biochem.2c00560.
Multidrug-resistant bacteria cause immense public health concerns as once effective antibiotics no longer work against even common infections. Concomitantly, there has been a decline in the discovery of new antibiotics, and the current global clinical pipeline is woefully inadequate, especially against resistant Gram-negative bacteria. One major contribution to Gram-negative resistance is the presence of a protective outer membrane. Consequently, an appealing option for tackling resistance is to adversely affect that outer membrane. With that in mind, we define the response regulator PhoP as a target for new 2-Aminoimidazole compounds and show that they affect the integrity of the outer membrane in resistant strains of Escherichia coli and Klebsiella pneumoniae. We also provide empirical evidence for the 2-Aminoimidazole mechanism of action.
2-Aminoimidazoles in medicinal chemistry
Mini Rev Med Chem 2013 Nov;13(13):1921-43.PMID:24070208DOI:10.2174/1389557511313130007.
2-Aminoimidazole skeleton represents a unique building block which is often used in the design of modulators of different targets and small molecule drugs. Alkaloids isolated from marine sponges are known to be one of the most common sources of the 2-Aminoimidazole compounds and from a medicinal chemistry perspective, the marine alkaloids' fascinating structures as well as their broad spectrum of pharmacological activity make them promising lead compounds for various druggable targets. This review will focus on the presentation of biologically evaluated 2-Aminoimidazole compounds showing a variety of pharmacological properties and their structure-activity relationship. The importance of 2-aminoimidazoles as bioisosteres of guanidine, acylguanidine, benzamidine and triazole groups will be highlighted.
2-Aminoimidazole-based antagonists of the 5-HT6 receptor - A new concept in aminergic GPCR ligand design
Eur J Med Chem 2019 Oct 1;179:1-15.PMID:31229883DOI:10.1016/j.ejmech.2019.06.001.
A new strategy in the design of aminergic GPCR ligands is proposed - the use of aromatic, heterocyclic basic moieties in place of the evergreen piperazine or alicyclic and aliphatic amines. This hypothesis has been tested using a benchmark series of 5-HT6R antagonists obtained by coupling variously substituted 2-Aminoimidazole moieties to the well established 1-benzenesulfonyl-1H-indoles, which served as the ligands cores. The crystallographic studies revealed that upon protonation, the 2-Aminoimidazole fragment triggers a resonance driven conformational change leading to a form of higher affinity. This molecular switch may be responsible for the observed differences in 5-HT6R activity of the studied chemotypes with different amine-like fragments. Considering the multiple functionalization sites of the embedded guanidine fragment, diverse libraries were constructed, and the relationships between the structure and activity, metabolic stability, and solubility were established. Compounds from the N-(1H-imidazol-2-yl)acylamide chemotype (10a-z) exhibited high affinity for 5-HT6R and very high selectivity over 5-HT1A, 5-HT2A, 5-HT7 and D2 receptors (negligible binding), which was attributed to their very weak basicity. The lead compound in the series 4-methyl-5-[1-(naphthalene-1-sulfonyl)-1H-indol-3-yl]-1H-imidazol-2-amine (9i) was shown to reverse the cognitive impairment caused by the administration of scopolamine in rats indicating procognitive potential.