Ampicillin (D-(-)-α-Aminobenzylpenicillin)
(Synonyms: 氨苄青霉素; D-(-)-α-Aminobenzylpenicillin) 目录号 : GC33975Ampicillin (D-(-)-α-Aminobenzylpenicillin)是一种广谱β-内酰胺类抗生素,可对抗多种革兰氏阳性菌和革兰氏阴性菌。
Cas No.:69-53-4
Sample solution is provided at 25 µL, 10mM.
Ampicillin (D-(-)-α-Aminobenzylpenicillin) is a broad-spectrum β-lactam antibiotic that is active against a wide range of Gram-positive and Gram-negative bacteria[1]. Ampicillin is a competitive inhibitor of transpeptidase, which is essential for bacterial cell wall formation[2]. Ampicillin belongs to the penicillin family and is used to prevent and treat a variety of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis[3].
In vitro, treatment of colorectal adenocarcinoma HT-29 cells with Ampicillin (10-100μM) for 24-72h resulted in a significant decrease in cell survival at the lowest concentration (10µM), while at other concentrations, the percentage of surviving cells increased with increasing doses[4]. Treatment of Staphylococcus aureus induced to be metal-resistant with Ampicillin (0-300μM) for 24h significantly inhibited the growth of cadmium-resistant strains, but did not inhibit the growth of lead-resistant strains[5]. Ampicillin treatment increased the adhesion force measured between bacterial cells and atomic force microscopy (AFM) tips, with the average adhesion values for Gram-positive bacteria and Gram-negative bacteria increasing by 74% and 34%, respectively[6].
In vivo, intraperitoneal administration of ampicillin (200 mg/kg) to mice with transient forebrain ischemia significantly reduced neuronal damage in the CA1 subfield of the hippocampus, increased the level of glutamate transporter-1 (GLT-1), and inhibited matrix metalloproteinase (MMP) activity after forebrain ischemia[7].
References:
[1] Petri W A. Penicillins, cephalosporins, and other β-lactam antibiotics[J]. Goodman & Gilman’s, The Pharmacologic Basis of Therapeutics, 2006: 1127-1154.
[2] Sutcliffe J G. Nucleotide sequence of the ampicillin resistance gene of Escherichia coli plasmid pBR322[J]. Proceedings of the National Academy of Sciences, 1978, 75(8): 3737-3741.
[3] Khatoon N, Alam H, Khan A, et al. Ampicillin silver nanoformulations against multidrug resistant bacteria[J]. Scientific Reports, 2019, 9(1): 6848.
[4] Hut E F, Radulescu M, Pilut N, et al. Two antibiotics, ampicillin and tetracycline, exert different effects in HT-29 colorectal adenocarcinoma cells in terms of cell viability and migration capacity[J]. Current Oncology, 2021, 28(4): 2466-2480.
[5] Chudobova D, Dostalova S, Blazkova I, et al. Effect of ampicillin, streptomycin, penicillin and tetracycline on metal resistant and non-resistant Staphylococcus aureus[J]. International journal of environmental research and public health, 2014, 11(3): 3233-3255.
[6] Laskowski D, Strzelecki J, Pawlak K, et al. Effect of ampicillin on adhesive properties of bacteria examined by atomic force microscopy[J]. Micron, 2018, 112: 84-90.
[7] Lee K E, Cho K O, Choi Y S, et al. The neuroprotective mechanism of ampicillin in a mouse model of transient forebrain ischemia[J]. The Korean Journal of Physiology & Pharmacology: Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology, 2016, 20(2): 185.
Ampicillin (D-(-)-α-Aminobenzylpenicillin)是一种广谱β-内酰胺类抗生素,可对抗多种革兰氏阳性菌和革兰氏阴性菌[1]。 Ampicillin是转肽酶的一种竞争性抑制剂,而转肽酶是细菌形成细胞壁所必需的[2]。Ampicillin属于青霉素家族,该药用于预防和治疗多种细菌感染,如呼吸道感染、尿路感染、脑膜炎、沙门氏菌病和心内膜炎[3]。
在体外,Ampicillin(10-100μM)处理结直肠腺癌HT-29细胞24-72h,最低浓度下(10µM)导致细胞存活率显著下降,而在其他浓度下,随着剂量的增加,存活细胞百分比更高[4]。Ampicillin(0-300μM)处理被诱导出金属抗性的金黄色葡萄球菌24h,显著抑制了镉抗性菌株的生长,并没有抑制铅抗性菌株的生长[5]。Ampicillin处理可增加细菌细胞和原子力显微镜(AFM)尖端之间测量到的粘附力,革兰氏阳性菌和革兰氏阴性菌的平均粘附力值分别增加了74%和34%[6]。
在体内,Ampicillin(200mg/kg)通过腹腔注射治疗短暂性前脑缺血小鼠,显著减轻了海马CA1亚区神经元的损伤,提高了谷氨酸转运蛋白-1(GLT-1)的水平,抑制了前脑缺血后基质金属蛋白酶(MMP)活性[7]。
Cell experiment [1]: | |
Cell lines | HT-29 cells |
Preparation method | Cells were treated with five different concentrations of tetracycline and ampicillin (10, 25, 50, 75, and 100 µM), both solubilized in DMSO. Cell viability was determined at three-time intervals (24, 48, and 72 h). |
Reaction Conditions | 10-100μM; 24-72 h |
Applications | The lowest concentration of Ampicillin (10µM) resulted in a significant decrease in cell viability, while at other concentrations, higher percentages of viable cells were observed with increasing doses. |
Animal experiment [2]: | |
Animal models | Male C57BL/6 mice |
Preparation method | Male C57BL/6 mice were anesthetized with halothane and subjected to bilateral common carotid artery occlusion for 40 min. Before transient forebrain ischemia, ampicillin (200 mg/kg, i.p.) or penicillin G (6,000 U/kg or 20,000 U/kg, i.p.) was administered daily for 5 days. |
Dosage form | 200mg/kg; i.p. |
Applications | The pretreatment with ampicillin but not with penicillin G significantly attenuated neuronal damage in the hippocampal CA1 subfield. |
References: |
Cas No. | 69-53-4 | SDF | |
别名 | 氨苄青霉素; D-(-)-α-Aminobenzylpenicillin | ||
Canonical SMILES | OC([C@@H]1N(C2=O)[C@]([C@@H]2NC([C@@H](C3=CC=CC=C3)N)=O)([H])SC1(C)C)=O | ||
分子式 | C16H19N3O4S | 分子量 | 349.4 |
溶解度 | 0.1 M NaOH: 25 mg/mL (71.55 mM); Water: 5 mg/mL (14.31 mM) | 储存条件 | 4°C, protect from light |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.862 mL | 14.3102 mL | 28.6205 mL |
5 mM | 0.5724 mL | 2.862 mL | 5.7241 mL |
10 mM | 0.2862 mL | 1.431 mL | 2.862 mL |
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