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Ampicillin (D-(-)-α-Aminobenzylpenicillin) Sale

(Synonyms: 氨苄青霉素; D-(-)-α-Aminobenzylpenicillin) 目录号 : GC33975

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。

Ampicillin (D-(-)-α-Aminobenzylpenicillin) Chemical Structure

Cas No.:69-53-4

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Description

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]

实验参考方法

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:
[1] 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.
[2]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.

化学性质

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 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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