Gardiquimod - Moligand™, ≥97% , CAS No.1020412-43-4

CAS: 1020412-43-4 Cat. No.: G274801 Fórmula: C₁₇H₂₃N₅O Peso molecular: 313.4 Número CE: 806-274-5

GRADE & PURITY Moligand™, ≥97%

Synonyms

1-[4-amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol | 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol | 1-(4-amino-2-ethylaminomethylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Visão geral

Biochem/physiol Actions

Gardiquimod is a potent and specific agonist for human or mouse Toll-like receptor 7 (TLR7). Also, at high concentration gardiquimod activates TLR8. Similarly to imiquimod, gardiquimod could mimic the effects of viral nucleic acids on the immune system.

Gardiquimod is developed as a new imidazoquinoline compound. It stimulates NF-κB (nuclear factor-κB) activation in cells expressing human or murine toll like receptor 7 (TLR7). Gardiquimod is found to be ten times more efficient than imiquimod. It induces splenocyte activation and prevents murine B16 melanoma growth and metastasis. Gardiquimod might serve as a therapeutic agent to prevent HIV-1 (human immunodeficiency virus - 1) transmission. It hinders the life cycle of HIV-1, by blocking the action of HIV-1 reverse transcriptase.

Specifications

Sinónimos

1-[4-amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol | 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol | 1-(4-amino-2-ethylaminomethylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Especificações e pureza

Moligand™, ≥97%

Mecanismos bioquímicos e fisiológicos

Selective TLR7 agonist. Inhibits HIV-1 reverse transcriptase. Induces pro-inflammatory cytokine production in thymocytes. Antiproliferative effects. Shows immunomodulatory effects in vivo. More active than Imiquimod.

Condições de armazenamento de armazenamento

Store at -20°C,Desiccated

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Tipo de ação

INHIBITOR

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥97%

Nomes e identificadores

Pubchem Sid

528770954

Sorrisos canónicos

CCNCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N

IUPAC Name

1-[4-amino-2-(ethylaminomethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

InChIKey

FHJATBIERQTCTN-UHFFFAOYSA-N

INCHI

1S/C17H23N5O/c1-4-19-9-13-21-14-15(22(13)10-17(2,3)23)11-7-5-6-8-12(11)20-16(14)18/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20)

SMILES isoméricas

CCNCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N

Peso molecular

313.4

Reaxy-Rn

19659786

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=19659786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Quinolines and derivatives
      • Subclass Imidazoquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Quinolines and derivatives
• Subclass: Imidazoquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Imidazoquinolines
• Alternative Parents: Aminoquinolines and derivatives Imidazo-[4,5-c]pyridines Aralkylamines Aminopyridines and derivatives N-substituted imidazoles Imidolactams Benzenoids Tertiary alcohols Heteroaromatic compounds Dialkylamines Azacyclic compounds Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Imidazoquinoline - Aminoquinoline - Imidazopyridine - Imidazo-[4,5-c]pyridine - Aminopyridine - Aralkylamine - N-substituted imidazole - Pyridine - Benzenoid - Imidolactam - Tertiary alcohol - Imidazole - Azole - Heteroaromatic compound - Secondary amine - Secondary aliphatic amine - Azacycle - Amine - Primary amine - Organooxygen compound - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as imidazoquinolines. These are aromatic heterocyclic compounds containing an imidazole ring fused to a quinoline ring system. In some configurations, the imidazole ring shares a nitrogen atom with the quinoline moiety.
• External Descriptors: Not available

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

Alvos associados (humanos)

TLR8 Tchem Toll-like receptor 8 (1853 Activities)

Discover Target: TLR8

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

Alvos associados (não humanos)

Tlr7 Toll-like receptor 7 (174 Activities)

Discover Target: Tlr7

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

Mecanismos de ação

Propriedades químicas e físicas

• Solubilidade: Soluble in DMSO to 100 mM
• Peso molecular: 313.400 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 313.19 Da
• Monoisotopic Mass: 313.19 Da
• Topological Polar Surface Area: 89.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 404.000
• 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