Cinoxacina - Moligand™, ≥99% , CAS No.28657-80-9

CAS: 28657-80-9 Cat. No.: C135059 Peso molecular: 262.22 Número EC: 249-133-8

GRADE & PURITY Moligand™, ≥99%

Synonyms

áCIDO (1,3)DIOXOLO(4,5-G)CINNOLINA-3- CARBOXÍLICO, 1-ETIL-1,4-DIHIDRO-4-OXO | Ácido (1,3)Dioxolo(4,5-g)cinolina-3-carboxílico, 1-etil-1,4-dihidro-4-oxo- | ácido 5-etil-8-oxo-5,8-dihidro-1,3-dioxa-5,6-diaza-ciclopenta[b]naftaleno-7-carboxílico | BPBio1_000

Storage

Conservar a -20°C

Shipped In

Hielera + almohadillas de hielo

Descripción general

descripción del producto：

La cinoxacina es una quinolona antibacteriana análoga al ácido oxolínico. El compuesto ha sido documentado para bloquear la síntesis de ADN throμgh inhibición de Topo II (ADN girasa), así como la topoisomerasa IV. Se ha observado que la cinoxacina bloquea tanto la topoisomerasa IV en líneas celulares procariotas como eucariotas. Debido a la actividad inhibidora de la Cinoxacina, el compuesto ha mostrado toxicidad contra las células eucariotas. Estudios in vitro han demostrado que el daño renal causado por la Cinoxacina se atribuye a la deposición de cristales de Cinoxacina en el tracto urinario. La Cinoxacina es un antimicrobiano sintético comúnmente utilizado en infecciones del tracto urinario causadas por Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella y Enterobacter. Es un inhibidor de la quinolona girasa. Se utiliza para estudiar el transportador renal de aniones orgánicos 1 (OAT1) de rata. Se utiliza para estudiar Streptococcus pyogenes resistentes a las fluoroquinolonas.

Specifications

Sinónimos

áCIDO (1, 3)DIOXOLO(4, 5-G)CINNOLINA-3- CARBOXÍLICO, 1-ETIL-1, 4-DIHIDRO-4-OXO | Ácido (1, 3)Dioxolo(4, 5-g)cinolina-3-carboxílico, 1-etil-1, 4-dihidro-4-oxo- | ácido 5-etil-8-oxo-5, 8-dihidro-1, 3-dioxa-5, 6-diaza-ciclopenta[b]naftaleno-7-carboxílico | BPBio1_000

Especificaciones y pureza

Moligand™, ≥99%

Mecanismos bioquímicos y fisiológicos

La cinoxacina interfiere en la replicación del ADN al inhibir la ADN girasa y la topoisomerasa IV (topo IV) mediante una estrecha unión al ADN. La cinoxacina permite la separación adecuada del ADN replicado. Por lo tanto, la inhibición de la Cinoxacina in

Condiciones de almacenamiento de almacenamiento

Conservar a -20°C

Enviado en

Hielera + almohadillas de hielo

Grado

Moligand™

Pureza

≥99%

Propiedades del producto

• ALogP: 2.1

Nombres e identificadores

• Pubchem Sid: 504750602
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750602
• Sonrisas canónicas: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
• IUPAC Name: 1-ethyl-4-oxo-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
• InChIKey: VDUWPHTZYNWKRN-UHFFFAOYSA-N
• INCHI: 1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)
• Isómeros SMILES: CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
• Peso molecular: 262.22
• Reaxy-Rn: 1084304
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1084304&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Diazanaphthalenes
      • Subclass Benzodiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinnolines
• Alternative Parents: Benzodioxoles Pyridazines and derivatives Benzenoids Vinylogous amides Heteroaromatic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cinnoline - Benzodioxole - Pyridazine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Oxacycle - Azacycle - Acetal - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring.
• External Descriptors: oxacycle - oxo carboxylic acid - cinnolines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

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Objetivos asociados (no humanos)

ampC Beta-lactamase AmpC (62480 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Faah Anandamide amidohydrolase (3907 Activities)

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MDH2 Malate dehydrogenase mitochondrial (131 Activities)

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Plasmodium yoelii yoelii (73 Activities)

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Plasmodium falciparum (966862 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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gyrB DNA gyrase (2092 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in alka line solutions (pH 10 or more), and most polar organic solvents.. Insoluble in water.
• Peso molecular: 262.220 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 262.059 Da
• Monoisotopic Mass: 262.059 Da
• Topological Polar Surface Area: 88.400 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 449.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Lin Yue, Min Wang, Imran Mahmood Khan, Sobia Niazi, Bin Wang, Xiaoyuan Ma, Zhouping Wang, Wenshui Xia.  (2021)  Preparation and characterization of chitosan oligosaccharide derivatives containing cinnamyl moieties with enhanced antibacterial activities.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2021.111663]

2. Feng Jiang, Guoping Wu, Wanrong Li, Jiajia Yang, Junli Yan, Yi Wang, Wenli Yao, Xue Zhou, Zhiyong He, Linjing Wu, Chaoda Xiao, Ting Xiao, Min Zhang, Xiangchun Shen, Ling Tao.  (2018)  Preparation and protective effects of 1,8-cineole-loaded self-microemulsifying drug delivery system on lipopolysaccharide-induced endothelial injury in mice.  EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES,      [PMID:30336203] [10.1016/j.ejps.2018.10.012]

3. He Tian-Fu, Wang Lang-Hong, Niu De-bao, Wen Qing-hui, Zeng Xin-An.  (2018)  Cinnamaldehyde inhibit Escherichia coli associated with membrane disruption and oxidative damage.  ARCHIVES OF MICROBIOLOGY,  201  (4): (451-458).  [PMID:30293114] [10.1007/s00203-018-1572-5]

4. Tian-Fu He, Zhi-Hong Zhang, Xin-An Zeng, Lang-Hong Wang, Charles S. Brennan.  (2017)  Determination of membrane disruption and genomic DNA binding of cinnamaldehyde to Escherichia coli by use of microbiological and spectroscopic techniques.  JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY,      [PMID:29306845] [10.1016/j.jphotobiol.2017.11.015]

5. Beibei Mao, Fei Qu, Shuyun Zhu, Jinmao You.  (2016)  Fluorescence turn-on strategy based on silver nanoclusters-Cu2+ system for trace detection of quinolones.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2016.04.174]