Gardiquimod | CAS#1020412-43-4 | TLR7 agonist

MedKoo Cat#: 563634 | Name: Gardiquimod free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Gardiquimod free base

CAS#1020412-43-4 (free base)

Theoretical Analysis

MedKoo Cat#: 563634

Name: Gardiquimod free base

CAS#: 1020412-43-4 (free base)

Chemical Formula: C17H23N5O

Exact Mass: 313.1903

Molecular Weight: 313.40

Elemental Analysis: C, 65.15; H, 7.40; N, 22.35; O, 5.10

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks

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Related CAS #

1020412-43-4 (free base) 2956183-81-4 (HCl) 1159840-61-5 (2TFA)

Synonym

Gardiquimod;

IUPAC/Chemical Name

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

InChi Key

FHJATBIERQTCTN-UHFFFAOYSA-N

InChi Code

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 Code

CC(O)(C)CN1C(CNCC)=NC2=C1C3=CC=CC=C3N=C2N

Appearance

Solid powder

Purity

>97% (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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gardiquimod, 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/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	63.82
	DMSO	20.0	63.82
	Ethanol	12.0	38.29
	PBS (pH 7.2)	0.2	0.64

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 313.40 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.

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. Toll-like 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:

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. Toll-like 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.

1: Kim S, Kaiser P, Borowska D, Vervelde L. Synergistic effect of co-stimulation of membrane and endosomal TLRs on chicken innate immune responses. Vet Immunol Immunopathol. 2018 May;199:15-21. doi: 10.1016/j.vetimm.2018.03.005. Epub 2018 Mar 19. PubMed PMID: 29678225. 2: Enosi Tuipulotu D, Netzler NE, Lun JH, Mackenzie JM, White PA. TLR7 Agonists Display Potent Antiviral Effects against Norovirus Infection via Innate Stimulation. Antimicrob Agents Chemother. 2018 Apr 26;62(5). pii: e02417-17. doi: 10.1128/AAC.02417-17. Print 2018 May. PubMed PMID: 29530841; PubMed Central PMCID: PMC5923118. 3: Rudra JS, Banasik BN, Milligan GN. A combined carrier-adjuvant system of peptide nanofibers and toll-like receptor agonists potentiates robust CD8+ T cell responses. Vaccine. 2018 Jan 25;36(4):438-441. doi: 10.1016/j.vaccine.2017.12.017. Epub 2017 Dec 14. PubMed PMID: 29248267; PubMed Central PMCID: PMC5769694. 4: Braun RO, Python S, Summerfield A. Porcine B Cell Subset Responses to Toll-like Receptor Ligands. Front Immunol. 2017 Aug 25;8:1044. doi: 10.3389/fimmu.2017.01044. eCollection 2017. PubMed PMID: 28890720; PubMed Central PMCID: PMC5574874. 5: Chi H, Li C, Zhao FS, Zhang L, Ng TB, Jin G, Sha O. Anti-tumor Activity of Toll-Like Receptor 7 Agonists. Front Pharmacol. 2017 May 31;8:304. doi: 10.3389/fphar.2017.00304. eCollection 2017. Review. PubMed PMID: 28620298; PubMed Central PMCID: PMC5450331. 6: Zhu Q, Kanneganti TD. Cutting Edge: Distinct Regulatory Mechanisms Control Proinflammatory Cytokines IL-18 and IL-1β. J Immunol. 2017 Jun 1;198(11):4210-4215. doi: 10.4049/jimmunol.1700352. Epub 2017 May 3. PubMed PMID: 28468974; PubMed Central PMCID: PMC5544497. 7: 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. 8: Seth A, Lee H, Cho MY, Park C, Korm S, Lee JY, Choi I, Lim YT, Hong KS. Combining vasculature disrupting agent and Toll-like receptor 7/8 agonist for cancer therapy. Oncotarget. 2017 Jan 17;8(3):5371-5381. doi: 10.18632/oncotarget.14260. PubMed PMID: 28036266; PubMed Central PMCID: PMC5354915. 9: Gupta N, Vedi S, Kunimoto DY, Agrawal B, Kumar R. Novel lipopeptides of ESAT-6 induce strong protective immunity against Mycobacterium tuberculosis: Routes of immunization and TLR agonists critically impact vaccine's efficacy. Vaccine. 2016 Nov 4;34(46):5677-5688. doi: 10.1016/j.vaccine.2016.08.075. Epub 2016 Sep 29. PubMed PMID: 27693020. 10: Liu Y, Guo X, Wu L, Yang M, Li Z, Gao Y, Liu S, Zhou G, Zhao J. Lipid rafts promote liver cancer cell proliferation and migration by up-regulation of TLR7 expression. Oncotarget. 2016 Sep 27;7(39):63856-63869. doi: 10.18632/oncotarget.11697. PubMed PMID: 27588480; PubMed Central PMCID: PMC5325409. 11: Nyberg WA, Espinosa A. Imiquimod induces ER stress and Ca(2+) influx independently of TLR7 and TLR8. Biochem Biophys Res Commun. 2016 May 13;473(4):789-794. doi: 10.1016/j.bbrc.2016.03.080. Epub 2016 Mar 19. PubMed PMID: 27003259. 12: Wang F, Jin R, Zou BB, Li L, Cheng FW, Luo X, Geng X, Zhang SQ. Activation of Toll-like receptor 7 regulates the expression of IFN-λ1, p53, PTEN, VEGF, TIMP-1 and MMP-9 in pancreatic cancer cells. Mol Med Rep. 2016 Feb;13(2):1807-12. doi: 10.3892/mmr.2015.4730. Epub 2015 Dec 29. PubMed PMID: 26718740. 13: 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. PubMed PMID: 26433159. 14: Zou BB, Wang F, Li L, Cheng FW, Jin R, Luo X, Zhu LX, Geng X, Zhang SQ. Activation of Toll-like receptor 7 inhibits the proliferation and migration, and induces the apoptosis of pancreatic cancer cells. Mol Med Rep. 2015 Oct;12(4):6079-85. doi: 10.3892/mmr.2015.4130. Epub 2015 Jul 28. PubMed PMID: 26238718. 15: Lee HJ, Kim KC, Han JA, Choi SS, Jung YJ. The early induction of suppressor of cytokine signaling 1 and the downregulation of toll-like receptors 7 and 9 induce tolerance in costimulated macrophages. Mol Cells. 2015 Jan 31;38(1):26-32. doi: 10.14348/molcells.2015.2136. Epub 2014 Dec 15. PubMed PMID: 25518931; PubMed Central PMCID: PMC4314129. 16: Bikker A, Kruize AA, van der Wurff-Jacobs KM, Peters RP, Kleinjan M, Redegeld F, de Jager W, Lafeber FP, van Roon JA. Interleukin-7 and Toll-like receptor 7 induce synergistic B cell and T cell activation. PLoS One. 2014 Apr 16;9(4):e94756. doi: 10.1371/journal.pone.0094756. eCollection 2014. PubMed PMID: 24740301; PubMed Central PMCID: PMC3989236. 17: Li L, Cheng FW, Wang F, Jia B, Luo X, Zhang SQ. The activation of TLR7 regulates the expression of VEGF, TIMP1, MMP2, IL-6, and IL-15 in Hela cells. Mol Cell Biochem. 2014 Apr;389(1-2):43-9. doi: 10.1007/s11010-013-1925-y. Epub 2013 Dec 18. PubMed PMID: 24347177. 18: Quan FS, Ko EJ, Kwon YM, Joo KH, Compans RW, Kang SM. Mucosal adjuvants for influenza virus-like particle vaccine. Viral Immunol. 2013 Dec;26(6):385-95. doi: 10.1089/vim.2013.0013. Epub 2013 Nov 16. PubMed PMID: 24236855; PubMed Central PMCID: PMC3868302. 19: 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. 20: Oumata N, Nguyen PH, Beringue V, Soubigou F, Pang Y, Desban N, Massacrier C, Morel Y, Paturel C, Contesse MA, Bouaziz S, Sanyal S, Galons H, Blondel M, Voisset C. The toll-like receptor agonist imiquimod is active against prions. PLoS One. 2013 Aug 16;8(8):e72112. doi: 10.1371/journal.pone.0072112. eCollection 2013. PubMed PMID: 23977222; PubMed Central PMCID: PMC3745460.