Gardiquimod TFA
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MedKoo CAT#: 330135

CAS#: 1159840-61-5 (TFA)

Description: Gardiquimod is a chemical compound which acts selectively at both mouse and human forms of toll-like receptor 7 (TLR7). It functions as an immune response modifier. The core structure is 1H-imidazo[4,5-c]quinoline, as found in related drugs such as imiquimod and resiquimod. It is structurally very similar to resiquimod differing only by an oxygen for nitrogen switch.


Chemical Structure

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Gardiquimod TFA
CAS# 1159840-61-5 (TFA)

Theoretical Analysis

MedKoo Cat#: 330135
Name: Gardiquimod TFA
CAS#: 1159840-61-5 (TFA)
Chemical Formula: C19H24F3N5O3
Exact Mass: 427.1831
Molecular Weight: 427.4282
Elemental Analysis: C, 53.39; H, 5.66; F, 13.33; N, 16.39; O, 11.23

Price and Availability

Size Price Availability Quantity
50.0mg USD 550.0 2 Weeks
100.0mg USD 950.0 2 Weeks
200.0mg USD 1650.0 2 Weeks
500.0mg USD 3250.0 2 Weeks
1.0g USD 5150.0 2 Weeks
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Related CAS #: 1159840-61-5 (TFA)   1020412-43-4 (free base)    

Synonym: Gardiquimod TFA salt; Gardiquimod;

IUPAC/Chemical Name: 1-(4-amino-2-((ethylamino)methyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol 2,2,2-trifluoroacetate

InChi Key: POTWNBLXWPBSSG-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H23N5O.C2HF3O2/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;3-2(4,5)1(6)7/h5-8,19,23H,4,9-10H2,1-3H3,(H2,18,20);(H,6,7)

SMILES Code: CC(O)(C)CN1C(CNCC)=NC2=C1C3=CC=CC=C3N=C2N.O=C(O)C(F)(F)F

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Gardiquimod diTFA, an imidazoquinoline analog, is a TLR7/8 agonist.
In vitro activity: Treatment of macrophages with gardiquimod on day 5 of culture, followed by infection with HIV-1Ba-L on day 8, significantly reduced levels of HIV-1 DNA in the cells (p≤0.001) at all gardiquimod concentrations tested compared to untreated controls, as determined on day 4 postinfection (Fig. 1). Reference: AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. https://pubmed.ncbi.nlm.nih.gov/23316755/
In vivo activity: GDQ (gardiquimod) infusion was associated with sustained moderate hypertension that resolved after 72 h recovery. Electrophysiologically, GDQ infusion was associated with reduced number and burden of postasphyxial seizures in preterm fetal sheep in the first 18 h of recovery (p < 0.05). Subsequently, GDQ was associated with induction of slow rhythmic epileptiform discharges (EDs) from 72 to 96 h of recovery (p < 0.05 vs asphyxia + vehicle). The total burden of EDs was associated with reduced numbers of neurons in the caudate nucleus (r2 = 0.61, p < 0.05) and CA1/2 hippocampal region (r2 = 0.66, p < 0.05). These data demonstrate that TLR7 activation by GDQ modulated blood pressure and suppressed seizures in the early phase of postasphyxial recovery, with subsequent prolonged induction of epileptiform activity. Reference: Int J Mol Sci. 2021 Jun 19;22(12):6593. https://pubmed.ncbi.nlm.nih.gov/34205464/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 116.98
Water 25.0 58.49

Preparing Stock Solutions

The following data is based on the product molecular weight 427.4282 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi: 10.1089/aid.2012.0313. Epub 2013 Feb 5. PMID: 23316755; PMCID: PMC3653394. 2. Zhou Z, Yu X, Zhang J, Tian Z, Zhang C. TLR7/8 agonists promote NK-DC cross-talk to enhance NK cell anti-tumor effects in hepatocellular carcinoma. Cancer Lett. 2015 Dec 28;369(2):298-306. doi: 10.1016/j.canlet.2015.09.017. Epub 2015 Oct 9. PMID: 26433159. 3. Cho KHT, Fraser M, Xu B, Dean JM, Gunn AJ, Bennet L. Induction of Tertiary Phase Epileptiform Discharges after Postasphyxial Infusion of a Toll-Like Receptor 7 Agonist in Preterm Fetal Sheep. Int J Mol Sci. 2021 Jun 19;22(12):6593. doi: 10.3390/ijms22126593. PMID: 34205464; PMCID: PMC8234830. 4. Leung PY, Stevens SL, Packard AE, Lessov NS, Yang T, Conrad VK, van den Dungen NN, Simon RP, Stenzel-Poore MP. Tolllike receptor 7 preconditioning induces robust neuroprotection against stroke by a novel type I interferon-mediated mechanism. Stroke. 2012 May;43(5):1383-9. doi: 10.1161/STROKEAHA.111.641522. Epub 2012 Mar 8. PMID: 22403050; PMCID: PMC3943206.
In vitro protocol: 1. Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7 agonist that inhibits HIV type 1 infection of human macrophages and activated T cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi: 10.1089/aid.2012.0313. Epub 2013 Feb 5. PMID: 23316755; PMCID: PMC3653394. 2. Zhou Z, Yu X, Zhang J, Tian Z, Zhang C. TLR7/8 agonists promote NK-DC cross-talk to enhance NK cell anti-tumor effects in hepatocellular carcinoma. Cancer Lett. 2015 Dec 28;369(2):298-306. doi: 10.1016/j.canlet.2015.09.017. Epub 2015 Oct 9. PMID: 26433159.
In vivo protocol: 1. Cho KHT, Fraser M, Xu B, Dean JM, Gunn AJ, Bennet L. Induction of Tertiary Phase Epileptiform Discharges after Postasphyxial Infusion of a Toll-Like Receptor 7 Agonist in Preterm Fetal Sheep. Int J Mol Sci. 2021 Jun 19;22(12):6593. doi: 10.3390/ijms22126593. PMID: 34205464; PMCID: PMC8234830. 2. Leung PY, Stevens SL, Packard AE, Lessov NS, Yang T, Conrad VK, van den Dungen NN, Simon RP, Stenzel-Poore MP. Tolllike receptor 7 preconditioning induces robust neuroprotection against stroke by a novel type I interferon-mediated mechanism. Stroke. 2012 May;43(5):1383-9. doi: 10.1161/STROKEAHA.111.641522. Epub 2012 Mar 8. PMID: 22403050; PMCID: PMC3943206.

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1: Guo S, Zhang Y, Wang Z, Yu Y, Wang G. Intraperitoneal gardiquimod protects
against hepatotoxicity through inhibition of oxidative stress and inflammation in
mice with sepsis. J Biochem Mol Toxicol. 2017 Aug;31(8). doi: 10.1002/jbt.21923.
Epub 2017 Apr 19. PubMed PMID: 28422377.

2: Jia B, Luo X, Cheng FW, Li L, Hu DJ, Wang F, Zhang SQ. Gardiquimod inhibits
the expression of calcium-induced differentiation markers in HaCaT cells. Mol
Biol Rep. 2013 Nov;40(11):6363-9. doi: 10.1007/s11033-013-2750-9. Epub 2013 Sep
22. PubMed PMID: 24057248.

3: Buitendijk M, Eszterhas SK, Howell AL. Gardiquimod: a Toll-like receptor-7
agonist that inhibits HIV type 1 infection of human macrophages and activated T
cells. AIDS Res Hum Retroviruses. 2013 Jun;29(6):907-18. doi:
10.1089/AID.2012.0313. Epub 2013 Feb 5. PubMed PMID: 23316755; PubMed Central
PMCID: PMC3653394.

4: Ma F, Zhang J, Zhang J, Zhang C. The TLR7 agonists imiquimod and gardiquimod
improve DC-based immunotherapy for melanoma in mice. Cell Mol Immunol. 2010
Sep;7(5):381-8. doi: 10.1038/cmi.2010.30. Epub 2010 Jun 14. PubMed PMID:
20543857; PubMed Central PMCID: PMC4002679.