5-Chloro-8-hydroxy-7-iodoquinoline - 10mM in DMSO , Iron chelating agent, CAS No.130-26-7, Iron chelating agent

CAS: 130-26-7 Cat. No.: C421179 Peso molecular: 305.5 Beilstein Registry Number: 153637 Número EC: 204-984-4

GRADE & PURITY 10mM in DMSO

Synonyms

clioquinol|130-26-7|5-Chloro-7-iodoquinolin-8-ol|Iodochlorhydroxyquin|Chinoform|Chloroiodoquin|5-Chloro-7-iodo-8-quinolinol|Chloroiodoquine|5-Chloro-8-hydroxy-7-iodoquinoline|Vioform|Iodochloroxyquinoline|Cliquinol|Iodochlorohydroxyquinoline|Chlorojodochi

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Clioquinol is a member of the hydroxyquinoline family which inhibits certain enzymes related to DNA replication. Clioquinol is a metal chelating ligand which displays protective effects in various neurodegenerative states as well as being a component in antifungal and antiprotozoal agents. It has been shown to modulate amyloid beta-peptide accumulation via upregulation of metalloprotease activity. When co-administered with vitamin B12, Clioquinol rescues lead-induced impairments of synaptic plasticity in an animal models. In recent animal studies Clioquinol has shown to reverse the progression of Parkinson's, Alzheimer's, and Huntington's diseases. Clioquinol has been observed to induce apoptosis in human cancer cell lines by generating free zinc in lysosomes.
A metal chelating ligand that inhibits certain enzymes related to DNA replication.

Specifications

Sinónimos

clioquinol | 130-26-7 | 5-Chloro-7-iodoquinolin-8-ol | Iodochlorhydroxyquin | Chinoform | Chloroiodoquin | 5-Chloro-7-iodo-8-quinolinol | Chloroiodoquine | 5-Chloro-8-hydroxy-7-iodoquinoline | Vioform | Iodochloroxyquinoline | Cliquinol | Iodochlorohydroxyquinoline | Chlorojodochi

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Metal chelator and ionophore with beneficial effects in animal models of neurodegenerative diseases (Alzheimer's, Parkinson's and Huntington's disease).

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

CHELATING AGENT

Mecanismo de acción

Iron chelating agent

Propiedades del producto

• ALogP: 3.5

Nombres e identificadores

• Sonrisas canónicas: C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
• IUPAC Name: 5-chloro-7-iodoquinolin-8-ol
• InChIKey: QCDFBFJGMNKBDO-UHFFFAOYSA-N
• INCHI: 1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
• Isómeros SMILES: C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
• WGK Alemania: 3
• RTECS: VC5075000
• Peso molecular: 305.5
• Beilstein: 153637
• Reaxy-Rn: 153637
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=153637&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Quinolines and derivatives
      • Subclass Haloquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Quinolines and derivatives
• Subclass: Haloquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Chloroquinolines
• Alternative Parents: 8-hydroxyquinolines O-iodophenols Pyridines and derivatives Aryl iodides Aryl chlorides Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organoiodides Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Chloroquinoline - 8-hydroxyquinoline - 2-iodophenol - Aryl chloride - Aryl halide - Aryl iodide - Pyridine - Benzenoid - Heteroaromatic compound - Azacycle - Organooxygen compound - Organonitrogen compound - Organoiodide - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as chloroquinolines. These are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
• External Descriptors: organoiodine compound - organochlorine compound - monohydroxyquinoline

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)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

COMT Tclin Catechol O-methyltransferase (404 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA3 Tclin Carbonic anhydrase III (753 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA6 Tclin Carbonic anhydrase VI (993 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA1 Tclin Carbonic anhydrase I (13240 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Ca7 Carbonic anhydrase VII (3 Activities)

Discover Target: Ca7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ttr Transthyretin (14 Activities)

Discover Target: Ttr

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp13 Matrix metalloproteinase 13 (19 Activities)

Discover Target: Mmp13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cruzipain (33337 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ca13 Carbonic anhydrase XIII (322 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA4 Carbonic anhydrase IV (1713 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp2 Matrix metalloproteinase-2 (12 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trichophyton benhamiae (1686 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Salmonella typhimurium (15756 Activities)

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Plesiomonas shigelloides (58 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Citrobacter freundii (1864 Activities)

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Escherichia coli (133304 Activities)

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Morganella morganii (1291 Activities)

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Salmonella enteritidis (727 Activities)

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Serratia marcescens (3237 Activities)

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Shigella dysenteriae (933 Activities)

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Aeromonas hydrophila (292 Activities)

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Aspergillus niger (16508 Activities)

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Bacillus subtilis (32866 Activities)

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Clostridium acetobutylicum (18 Activities)

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Listeria monocytogenes (2626 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Pneumocystis carinii (749 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Enterococcus faecalis (29875 Activities)

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Bacillus cereus (7522 Activities)

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Corynebacterium diphtheriae (64 Activities)

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Cutibacterium acnes (887 Activities)

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Aspergillus oryzae (433 Activities)

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Leishmania infantum (5912 Activities)

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Trypanosoma brucei (78846 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Entamoeba histolytica (2676 Activities)

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Cryptosporidium parvum (1150 Activities)

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Plasmodium falciparum (966862 Activities)

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Tetrahymena thermophila (42 Activities)

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Albifimbria verrucaria (26 Activities)

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Candida (1648 Activities)

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Candida albicans (78123 Activities)

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Trichoderma viride (1263 Activities)

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Leishmania amazonensis (3813 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Light sensitive
• Punto de fusión (°C): 175°C
• Peso molecular: 305.500 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 304.91 Da
• Monoisotopic Mass: 304.91 Da
• Topological Polar Surface Area: 33.100 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 192.000
• 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. Qin Tan, Xuanxuan An, Shuang Pan, Shujun Zhen, Yongmei Hu, Xiaoli Hu.  (2021)  One-pot hydrothermal method synthesis carbon dots as a fluorescent sensor for the sensitive and selective detection of clioquinol.  OPTICAL MATERIALS,      [PMID:] [10.1016/j.optmat.2021.111830]

2. Lijun Xu, Jialin Sai, Dongguo Xue, Lu Zhou, Renjun Pei, Aihua Liu.  (2021)  Amplified Peroxidase-like Activity of Co2+ Using 8-Hydroxyquinoline and Its Application for Ultrasensitive Colorimetric Detection of Clioquinol.  Chemistry-An Asian Journal,  16  (23): (3957-3962).  [PMID:34605211] [10.1002/asia.202100997]