GTS-21 | CAS#148372-04-7 | anti-inflammatory

MedKoo Cat#: 584410 | Name: GTS-21

Description:

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

GTS-21 is an alpha7nAChR nicotinic receptor agonist found to inhibit the inflammation associated with rheumatoid arthritis (RA) by inhibiting RA Th1-cell differentiation.

Chemical Structure

GTS-21

CAS#148372-04-7 (free base)

Theoretical Analysis

MedKoo Cat#: 584410

Name: GTS-21

CAS#: 148372-04-7 (free base)

Chemical Formula: C19H20N2O2

Exact Mass: 308.1525

Molecular Weight: 308.38

Elemental Analysis: C, 74.00; H, 6.54; N, 9.08; O, 10.38

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

148372-04-7 (free base) 156223-05-1 (HCl)

Synonym

GTS-21; GTS21; GTS 21; DMXB-A

IUPAC/Chemical Name

2,3'-Bipyridine, 3-((2,4-dimethoxyphenyl)methylene)-3,4,5,6-tetrahydro-, (3E)-

InChi Key

RPYWXZCFYPVCNQ-RVDMUPIBSA-N

InChi Code

InChI=1S/C19H20N2O2/c1-22-17-8-7-14(18(12-17)23-2)11-15-5-4-10-21-19(15)16-6-3-9-20-13-16/h3,6-9,11-13H,4-5,10H2,1-2H3/b15-11+

SMILES Code

COC1=CC=C(/C=C2C(C3=CC=CN=C3)=NCCC/2)C(OC)=C1

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 308.38 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

1: Yue Y, Liu R, Cheng W, Hu Y, Li J, Pan X, Peng J, Zhang P. GTS-21 attenuates lipopolysaccharide-induced inflammatory cytokine production in vitro by modulating the Akt and NF-κB signaling pathway through the α7 nicotinic acetylcholine receptor. Int Immunopharmacol. 2015 Dec;29(2):504-512. doi: 10.1016/j.intimp.2015.10.005. Epub 2015 Oct 18. PubMed PMID: 26490221. 2: Kong FJ, Ma LL, Zhang HH, Zhou JQ. Alpha 7 nicotinic acetylcholine receptor agonist GTS-21 mitigates isoflurane-induced cognitive impairment in aged rats. J Surg Res. 2015 Mar;194(1):255-61. doi: 10.1016/j.jss.2014.09.043. Epub 2014 Oct 5. PubMed PMID: 25450597. 3: Hu Y, Liu R, Li J, Yue Y, Cheng W, Zhang P. Attenuation of Collagen-Induced Arthritis in rat by nicotinic alpha7 receptor partial agonist GTS-21. Biomed Res Int. 2014;2014:325875. doi: 10.1155/2014/325875. Epub 2014 Feb 27. PubMed PMID: 24719855; PubMed Central PMCID: PMC3955649. 4: Callahan PM, Terry AV Jr, Tehim A. Effects of the nicotinic α7 receptor partial agonist GTS-21 on NMDA-glutamatergic receptor related deficits in sensorimotor gating and recognition memory in rats. Psychopharmacology (Berl). 2014 Sep;231(18):3695-706. doi: 10.1007/s00213-014-3509-2. Epub 2014 Mar 5. PubMed PMID: 24595504; PubMed Central PMCID: PMC4748388. 5: Sitapara RA, Antoine DJ, Sharma L, Patel VS, Ashby CR Jr, Gorasiya S, Yang H, Zur M, Mantell LL. The α7 nicotinic acetylcholine receptor agonist GTS-21 improves bacterial clearance in mice by restoring hyperoxia-compromised macrophage function. Mol Med. 2014 Jun 19;20:238-47. doi: 10.2119/molmed.2013.00086. PubMed PMID: 24664237; PubMed Central PMCID: PMC4069272. 6: Wu S, Zhao H, Luo H, Xiao X, Zhang H, Li T, Zuo X. GTS-21, an α7-nicotinic acetylcholine receptor agonist, modulates Th1 differentiation in CD4(+) T cells from patients with rheumatoid arthritis. Exp Ther Med. 2014 Aug;8(2):557-562. Epub 2014 Jun 3. PubMed PMID: 25009619; PubMed Central PMCID: PMC4079428. 7: Nullens S, Staessens M, Peleman C, Schrijvers DM, Malhotra-Kumar S, Francque S, Matteoli G, Boeckxstaens GE, De Man JG, De Winter BY. EFFECT OF GTS-21, AN ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONIST, ON CLP-INDUCED INFLAMMATORY, GASTROINTESTINAL MOTILITY, AND COLONIC PERMEABILITY CHANGES IN MICE. Shock. 2016 Apr;45(4):450-9. doi: 10.1097/SHK.0000000000000519. PubMed PMID: 26618987. 8: Cannon CE, Puri V, Vivian JA, Egbertson MS, Eddins D, Uslaner JM. The nicotinic α7 receptor agonist GTS-21 improves cognitive performance in ketamine impaired rhesus monkeys. Neuropharmacology. 2013 Jan;64:191-6. doi: 10.1016/j.neuropharm.2012.05.003. Epub 2012 May 29. PubMed PMID: 22659472. 9: Kox M, Pompe JC, Gordinou de Gouberville MC, van der Hoeven JG, Hoedemaekers CW, Pickkers P. Effects of the α7 nicotinic acetylcholine receptor agonist GTS-21 on the innate immune response in humans. Shock. 2011 Jul;36(1):5-11. doi: 10.1097/SHK.0b013e3182168d56. PubMed PMID: 21368716. 10: Khan MA, Farkhondeh M, Crombie J, Jacobson L, Kaneki M, Martyn JA. Lipopolysaccharide upregulates α7 acetylcholine receptors: stimulation with GTS-21 mitigates growth arrest of macrophages and improves survival in burned mice. Shock. 2012 Aug;38(2):213-9. doi: 10.1097/SHK.0b013e31825d628c. PubMed PMID: 22683726; PubMed Central PMCID: PMC3399057. 11: Kox M, Pompe JC, Peters E, Vaneker M, van der Laak JW, van der Hoeven JG, Scheffer GJ, Hoedemaekers CW, Pickkers P. α7 nicotinic acetylcholine receptor agonist GTS-21 attenuates ventilator-induced tumour necrosis factor-α production and lung injury. Br J Anaesth. 2011 Oct;107(4):559-66. doi: 10.1093/bja/aer202. Epub 2011 Jul 18. PubMed PMID: 21771746. 12: Schmidt K, Bhakdisongkhram S, Uhle F, Philipsenburg C, Zivkovic AR, Brenner T, Motsch J, Weigand MA, Hofer S. GTS-21 reduces microvascular permeability during experimental endotoxemia. Microvasc Res. 2018 Jan;115:75-82. doi: 10.1016/j.mvr.2017.08.002. Epub 2017 Aug 15. PubMed PMID: 28818494. 13: Thomsen MS, Mikkelsen JD. The α7 nicotinic acetylcholine receptor ligands methyllycaconitine, NS6740 and GTS-21 reduce lipopolysaccharide-induced TNF-α release from microglia. J Neuroimmunol. 2012 Oct 15;251(1-2):65-72. doi: 10.1016/j.jneuroim.2012.07.006. Epub 2012 Aug 9. PubMed PMID: 22884467. 14: Stokes C, Papke JK, Horenstein NA, Kem WR, McCormack TJ, Papke RL. The structural basis for GTS-21 selectivity between human and rat nicotinic alpha7 receptors. Mol Pharmacol. 2004 Jul;66(1):14-24. PubMed PMID: 15213292. 15: Azuma R, Komuro M, Black SR, Mathews JM. The effect of repeat administration of GTS-21 on mixed-function oxidase activities in rat. Toxicol Lett. 1999 Nov 22;110(3):137-44. PubMed PMID: 10597024. 16: Gao Y, Kang K, Liu H, Kong W, Han Q, Zhang X, Huang R, Qu J, Wang H, Wang S, Liu R, Liu Y, Yu K. GTS-21 attenuates LPS-induced renal injury via the cholinergic anti-inflammatory pathway in mice. Am J Transl Res. 2017 Oct 15;9(10):4673-4681. eCollection 2017. PubMed PMID: 29118926; PubMed Central PMCID: PMC5666073. 17: Nanri M, Kasahara N, Yamamoto J, Miyake H, Watanabe H. A comparative study on the effects of nicotine and GTS-21, a new nicotinic agonist, on the locomotor activity and brain monoamine level. Jpn J Pharmacol. 1998 Nov;78(3):385-9. PubMed PMID: 9869274. 18: Yang X, Zhao C, Chen X, Jiang L, Su X. Monocytes primed with GTS-21/α7 nAChR (nicotinic acetylcholine receptor) agonist develop anti-inflammatory memory. QJM. 2017 Jul 1;110(7):437-445. doi: 10.1093/qjmed/hcx014. PubMed PMID: 28082382. 19: Kox M, van Velzen JF, Pompe JC, Hoedemaekers CW, van der Hoeven JG, Pickkers P. GTS-21 inhibits pro-inflammatory cytokine release independent of the Toll-like receptor stimulated via a transcriptional mechanism involving JAK2 activation. Biochem Pharmacol. 2009 Oct 1;78(7):863-72. doi: 10.1016/j.bcp.2009.06.096. Epub 2009 Jul 1. PubMed PMID: 19576181. 20: Azuma R, Hirota T, Manabe H, Komuro M, Kiwada H. First-pass of GTS-21 on canine gut wall and liver determined by portal-systemic concentration difference. Eur J Pharm Sci. 2001 Sep;14(2):159-65. PubMed PMID: 11500261.