ナリジクス酸
カタログ番号:
B1676918
CAS番号:
389-08-2
分子量:
232.23 g/mol
InChIキー:
MHWLWQUZZRMNGJ-UHFFFAOYSA-N
注意:
研究専用です。人間または獣医用ではありません。
概要
説明
- ナリジクス酸は、ネビグラモン、ネグラム、ウィンミロン、WIN 18,320などの商品名でも知られており、最初の合成キノロン系抗生物質です。
- 厳密には、キノロン系ではなくナフチリドン系に属します。 その環構造は、キノリンのように窒素原子を1つしか持たないのではなく、2つの窒素原子を含む1,8-ナフチリジン核です .
製造方法
- ナリジクス酸は、2-メチルピリジンから2-アミノ-5-メチルピリジンを形成することによって合成されます。
- この化合物は次に、ギ酸エチルとシュウ酸ジエチルと縮合して、N-(2-メチル-5-アミノ-ピリジン)メチレンマロネートを生成します。
- 260〜270°Cでの環化に続いて、水酸化ナトリウムによる加水分解を行うと、7-メチル-1,8-ナフチリジン-4-ヒドロキシ-3-カルボン酸が得られます。
- 最後に、ブロモエタンによるN-アルキル化により、ナリジクス酸が得られます .
作用機序
- ナリジクス酸は、細菌のDNAジャイレース（トポイソメラーゼII）を阻害し、DNAの複製と転写を防ぎます。
- DNAのスーパーコイル干渉し、細胞死を引き起こします。
- この化合物の分子標的は、細菌のトポイソメラーゼです .
科学的研究の応用
- Nalidixic acid is primarily used to treat urinary tract infections caused by susceptible Gram-negative rods (e.g., Escherichia coli, Klebsiella spp.).
- due to increasing resistance, it is essential to select antibiotics based on susceptibility testing results .
生化学分析
Biochemical Properties
Nalidixic acid plays a crucial role in biochemical reactions by targeting bacterial DNA gyrase and topoisomerase IV, enzymes essential for DNA replication and transcription. By inhibiting these enzymes, nalidixic acid prevents the supercoiling and uncoiling of bacterial DNA, thereby halting DNA synthesis. This interaction is specific to bacterial enzymes, making nalidixic acid effective against bacterial infections while having minimal impact on human cells .
Cellular Effects
Nalidixic acid exerts significant effects on various types of cells, particularly bacterial cells. It disrupts cell function by inhibiting DNA synthesis, leading to cell death. In bacterial cells, nalidixic acid affects cell signaling pathways, gene expression, and cellular metabolism. The inhibition of DNA gyrase and topoisomerase IV results in the accumulation of DNA breaks, which triggers the bacterial SOS response and ultimately leads to cell death .
Molecular Mechanism
The molecular mechanism of nalidixic acid involves its binding to the A subunit of DNA gyrase and the C subunit of topoisomerase IV. This binding interferes with the enzymes’ ability to introduce negative supercoils into DNA, which is essential for DNA replication and transcription. By stabilizing the DNA-enzyme complex, nalidixic acid prevents the re-ligation of DNA strands, leading to the accumulation of DNA breaks and inhibition of bacterial growth .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of nalidixic acid change over time. Initially, nalidixic acid rapidly inhibits DNA synthesis, leading to a decrease in bacterial growth. Over time, the stability and degradation of nalidixic acid can influence its effectiveness. Studies have shown that nalidixic acid is relatively stable under laboratory conditions, but prolonged exposure can lead to the development of bacterial resistance .
Dosage Effects in Animal Models
The effects of nalidixic acid vary with different dosages in animal models. At therapeutic doses, nalidixic acid effectively treats bacterial infections without causing significant toxicity. At high doses, nalidixic acid can exhibit toxic effects, including gastrointestinal disturbances and central nervous system toxicity. Threshold effects have been observed, where increasing the dosage beyond a certain point does not significantly enhance its antibacterial activity but increases the risk of adverse effects .
Metabolic Pathways
Nalidixic acid is metabolized in the liver, primarily through hydroxylation to form hydroxynalidixic acid. This metabolite retains antibacterial activity and contributes to the overall effectiveness of nalidixic acid. The metabolic pathways involve enzymes such as cytochrome P450, which facilitate the conversion of nalidixic acid to its active metabolite. The presence of hydroxynalidixic acid in the bloodstream ensures sustained antibacterial activity .
Transport and Distribution
Nalidixic acid is transported and distributed within cells and tissues through passive diffusion. It can cross cell membranes and accumulate in bacterial cells, where it exerts its antibacterial effects. The distribution of nalidixic acid within tissues is influenced by factors such as blood flow and tissue permeability. Transporters and binding proteins may also play a role in the cellular uptake and distribution of nalidixic acid .
Subcellular Localization
Nalidixic acid primarily localizes in the cytoplasm of bacterial cells, where it interacts with DNA gyrase and topoisomerase IV. The subcellular localization of nalidixic acid is crucial for its antibacterial activity, as it needs to reach its target enzymes to inhibit DNA synthesis. Post-translational modifications and targeting signals may influence the localization and activity of nalidixic acid within bacterial cells .
準備方法
- Nalidixic acid is synthesized from 2-methylpyridine to form 2-amino-5-methylpyridine.
- The latter compound is then condensed with ethyl formate and diethyl oxalate to produce N-(2-methyl-5-amino-pyridine)methylene malonate.
- Cyclization at 260-270°C followed by hydrolysis with sodium hydroxide yields 7-methyl-1,8-naphthyridine-4-hydroxy-3-carboxylic acid.
- Finally, N-alkylation with bromoethane leads to nalidixic acid .
化学反応の分析
- ナリジクス酸は、グラム陰性菌および一部のグラム陽性菌に対して抗菌活性を示します。
- 低濃度では静菌的に、高濃度では殺菌的に作用します。
- 一般的な反応には、加水分解、アルキル化、酸化などがあります。
- 生成される主要な生成物には、7-メチル-1,8-ナフチリジン-4-ヒドロキシ-3-カルボン酸とその誘導体があります .
科学研究への応用
- ナリジクス酸は、感受性のあるグラム陰性桿菌（例：大腸菌、クレブシエラ属）が原因の尿路感染症の治療に主に使用されます。
- 耐性の増加により、感受性試験の結果に基づいて抗生物質を選択することが不可欠です .
類似化合物との比較
- ナリジクス酸は、ナフチリドン構造を持つため、ユニークです。
- 類似の化合物には、シプロフロキサシン、レボフロキサシン、モキシフロキサシンなどの他のキノロン系抗生物質が含まれます .
特性
IUPAC Name |
1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
MHWLWQUZZRMNGJ-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H12N2O3 |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
3374-05-8 (hydrochloride salt, anhydrous) |
Source
|
| Record name | Nalidixic acid [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000389082 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID3020912 |
Source
|
| Record name | Nalidixic acid | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3020912 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
232.23 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Nalidixic acid is a cream-colored powder. (NTP, 1992), Solid |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014917 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
less than 1 mg/mL at 70 °F (NTP, 1992), Soly at 23 °C (mg/ml): chloroform 35; toluene 1.6; methanol 1.3; ethanol 0.6; water 0.1; ether 0.1., PRACTICALLY INSOL IN WATER; SOL IN SOLN OF CARBONATES, 2.30e+00 g/L |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nalidixic acid | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00779 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | NALIDIXIC ACID | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3241 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014917 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis., IT APPEARS TO ACT BY INHIBITING DNA SYNTH. |
Source
|
| Record name | Nalidixic acid | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00779 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | NALIDIXIC ACID | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3241 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
PALE BUFF, CRYSTALLINE POWDER, WHITE TO SLIGHTLY YELLOW, CRYSTALLINE POWDER | |
CAS No. |
389-08-2 |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nalidixic acid | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=389-08-2 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Nalidixic acid [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000389082 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Nalidixic acid | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00779 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | nalidixic acid | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=757432 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | nalidixic acid | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=82174 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | Nalidixic acid | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3020912 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Nalidixic acid | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.006.241 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | NALIDIXIC ACID | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/3B91HWA56M | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | NALIDIXIC ACID | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3241 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014917 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
444 to 446 °F (NTP, 1992), 229-230 °C, 229.5 °C |
Source
|
| Record name | NALIDIXIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20720 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nalidixic acid | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00779 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | NALIDIXIC ACID | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3241 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Nalidixic Acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014917 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Synthesis routes and methods I
Procedure details
The culture medium LB (Tryptone 10 g/L, yeast extract 5 g/L, NaCl 10 g/L) that once autoclaved was supplemented with 25 μg/mL of kanamycin was used to grow E. coli S17-1 λ pir. Once the stationary phase was achieved, 0.2-0.3 A600 units of the App culture and 0.6-0.8 A600 units of the E. coli culture were added to 1 mL of a 10 mM solution of MgSO4. Next it was centrifuged during 2 minutes at 15,000 g and the pellet so obtained was resuspended in 200 μl of a 10 mM MgSO4 solution. Once the mixture of both cultures had been done, this was extended on a 2.5 cm and 0.45 μM nitrocellulose filter previously placed on a Petri dish containing TSYN medium supplemented with 15 g/L Noble agar. After incubation during 6 hours at 37 C., the filter with the conjugation was placed in a tube containing 2 mL of PBS (Na2HPO410 mM, KH2PO4 1 mM, NaCl 137 mM, KCl 2 mM pH 7.4). After vigorous shaking, the filter was removed and the cell suspension was centrifuged during 2 minutes at 15,000 g and the pellet was resuspended in 500 μL of PBS. The so obtained suspension was distributed in Petri dishes with TSYN medium supplemented with 15 g/L Noble Agar, 50 μg/mL kanamycin and 50 μg/mL nalidixic acid, at a rate of 100 μL of cell suspension for each Petri dish. The resulting cultures were incubated at 37 C. for 24-36 hours. With this procedure 65 colonies resistant to kanamicin and nalidixic acid, were obtained for the conjugation with the plasmid pApxIΔH2, which equals a frequency of transformation of 1.3×10−7 for each receptor cell.
[Compound]
Name
nitrocellulose
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
kanamycin
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Name
Synthesis routes and methods II
Procedure details
85 mutant strains obtained above were inoculated in a 8 ml LB medium containing 50 μg/ml ampicillin in a large test tube, and cultured at 30° C. for 17 hr. The culture medium was inoculated at 1% in a 8 ml medium containing 100 μg/ml ampicillin [16 g/L dipotassium hydrogen phosphate, 14 g/L potassium dihydrogen phosphate, 5 g/L ammonium sulfate, 1 g/L citric acid (anhydrous), 5 g/L casamino acid (manufactured by Difco), 10 g/L glucose, 10 mg/L vitamin B1, 25 mg/L magnesium sulfate heptahydrate, 50 mg/L iron sulfate heptahydrate, 100 mg/L L-proline, adjusted with 10 mol/L sodium hydroxide to pH 7.2, and glucose, vitamin B1, magnesium sulfate heptahydrate and iron sulfate heptahydrate were separately autoclaved and added] in a test tube, and cultured at 30° C. for 24 hr. The culture medium was centrifuged and a culture supernatant was obtained. The accumulated amounts of L-glutamine and L-glutamic acid in the culture supernatant were quantified by high performance liquid chromatography (HPLC), and productivity of L-glutamine and L-glutamic acid was evaluated.
Name
iron sulfate heptahydrate
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Ten
Name
dipotassium hydrogen phosphate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
Name
potassium dihydrogen phosphate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
Name
iron sulfate heptahydrate
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Eleven
Name
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Reactant of Route 1
Nalidixic acid
Reactant of Route 2
Nalidixic acid
Reactant of Route 3
Nalidixic acid
Reactant of Route 4
Reactant of Route 4
Nalidixic acid
Reactant of Route 5
Reactant of Route 5
Nalidixic acid
Reactant of Route 6
Nalidixic acid
試験管内研究製品の免責事項と情報
BenchChemで提示されるすべての記事および製品情報は、情報提供を目的としています。BenchChemで購入可能な製品は、生体外研究のために特別に設計されています。生体外研究は、ラテン語の "in glass" に由来し、生物体の外で行われる実験を指します。これらの製品は医薬品または薬として分類されておらず、FDAから任何の医療状態、病気、または疾患の予防、治療、または治癒のために承認されていません。これらの製品を人間または動物に体内に導入する形態は、法律により厳格に禁止されています。これらのガイドラインに従うことは、研究と実験において法的および倫理的な基準の遵守を確実にするために重要です。
![[(1r,2s,4s,5s)-4-[2-Iodo-6-(Methylamino)-9h-Purin-9-Yl]-2-(Phosphonooxy)bicyclo[3.1.0]hex-1-Yl]methyl Dihydrogen Phosphate](/img/structure/B1676837.png)
[(1r,2s,4s,5s)-4-[2-Iodo-6-(Methylamino)-9h-Purin-9-Yl]...
Cat. No.: B1676837
CAS No.: 779323-43-2
Flavone, 2',3,4',5,7-pentamethoxy-
Cat. No.: B1676841
CAS No.: 7555-80-8
3,5,7-Trimethoxyflavone
Cat. No.: B1676842
CAS No.: 26964-29-4
![N-(5-Pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide](/img/structure/B1676843.png)
N-(5-Pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)butyra...
Cat. No.: B1676843
CAS No.: 405221-09-2
![2-bromo-N-(4-(8-methylimidazo[1,2-a]pyridin-2-yl)phenyl)benzamide](/img/structure/B1676849.png)
![1-Quinolin-5-yloxy-3-[4-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)piperazin-1-yl]propan-2-ol](/img/structure/B1676850.png)
