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Key Documents

SML0877

Sigma-Aldrich

Gardiquimod

≥98% (HPLC)

Synonym(s):

1-(4-Amino-2-ethylaminomethylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, 4-Amino-2-[(ethylamino)methyl]-?,?-dimethyl-1H-Imidazo[4,5-c]quinoline-1-ethanol

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About This Item

Empirical Formula (Hill Notation):
C17H23N5O
CAS Number:
1020412-43-4
Molecular Weight:
313.40
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

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.

Features and Benefits

This compound is featured on the Cytokine Receptors (Interleukin-1 Receptor/TIR Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The TLR7 agonists imiquimod and gardiquimod improve DC-based immunotherapy for melanoma in mice
Ma F, et al.
Cellular & Molecular Immunology, 7(5), 381-381 (2010)
Maarten Buitendijk et al.
AIDS research and human retroviruses, 29(6), 907-918 (2013-01-16)
Immune response modifiers are being studied as therapeutic agents for viral infections and cancer. These molecules include agonists for the Toll-like receptors (TLR), a family of innate immune receptors. TLR7 and 8, located in cellular endosomes, bind single-stranded RNA characteristic
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Journal for immunotherapy of cancer, 9(9) (2021-09-04)
Immunization with tumor neoantigens is a promising vaccine approach to promote antitumor immunity due to their high immunogenicity, lack of expression in normal tissue, and preferential induction of tumor neoantigen-specific T cells, which are central mediators of the anti-cancer response.

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