GAT107

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

MedKoo CAT#: 530939

CAS#: 1476807-74-5

Description: GAT107 is an allosteric activator and positive modulator of α7 nicotinic acetylcholine receptors (nAChR). GAT107 is the bioactive enantiomer of 4BP-TQS. GAT107 reverses nociception in mouse models of inflammatory and neuropathic pain.


Price and Availability

Size
Price

Size
Price

Size
Price

GAT107 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 530939
Name: GAT107
CAS#: 1476807-74-5
Chemical Formula: C18H17BrN2O2S
Exact Mass: 404.0194
Molecular Weight: 405.31
Elemental Analysis: C, 53.34; H, 4.23; Br, 19.71; N, 6.91; O, 7.89; S, 7.91


Synonym: GAT107; GAT-107; GAT 107.

IUPAC/Chemical Name: (3aR,4S,9bS)-4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide

InChi Key: YNCXHXYZTLIZTO-HDMKZQKVSA-N

InChi Code: InChI=1S/C18H17BrN2O2S/c19-12-6-4-11(5-7-12)18-15-3-1-2-14(15)16-10-13(24(20,22)23)8-9-17(16)21-18/h1-2,4-10,14-15,18,21H,3H2,(H2,20,22,23)/t14-,15+,18+/m0/s1

SMILES Code: O=S(C1=CC2=C(N[C@H](C3=CC=C(Br)C=C3)[C@H]4[C@@H]2C=CC4)C=C1)(N)=O


Technical Data

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).

Harmonized System Code:
293490


References

1: Papke RL, Horenstein NA, Kulkarni AR, Stokes C, Corrie LW, Maeng CY, Thakur GA. The activity of GAT107, an allosteric activator and positive modulator of α7 nicotinic acetylcholine receptors (nAChR), is regulated by aromatic amino acids that span the subunit interface. J Biol Chem. 2014 Feb 14;289(7):4515-31. doi: 10.1074/jbc.M113.524603. Epub 2013 Dec 20. PubMed PMID: 24362025; PubMed Central PMCID: PMC3924313.

2: Bagdas D, Wilkerson JL, Kulkarni A, Toma W, AlSharari S, Gul Z, Lichtman AH, Papke RL, Thakur GA, Damaj MI. The α7 nicotinic receptor dual allosteric agonist and positive allosteric modulator GAT107 reverses nociception in mouse models of inflammatory and neuropathic pain. Br J Pharmacol. 2016 Aug;173(16):2506-20. doi: 10.1111/bph.13528. Epub 2016 Jul 18. PubMed PMID: 27243753; PubMed Central PMCID: PMC4959951.

3: Papke RL, Stokes C, Damaj MI, Thakur GA, Manther K, Treinin M, Bagdas D, Kulkarni AR, Horenstein NA. Persistent activation of α7 nicotinic ACh receptors associated with stable induction of different desensitized states. Br J Pharmacol. 2017 May 6. doi: 10.1111/bph.13851. [Epub ahead of print] PubMed PMID: 28477386.

4: Donvito G, Bagdas D, Toma W, Rahimpour E, Jackson A, Meade JA, AlSharari S, Kulkarni AR, Ivy Carroll F, Lichtman AH, Papke RL, Thakur GA, Imad Damaj M. The interaction between alpha 7 nicotinic acetylcholine receptor and nuclear peroxisome proliferator-activated receptor-α represents a new antinociceptive signaling pathway in mice. Exp Neurol. 2017 Sep;295:194-201. doi: 10.1016/j.expneurol.2017.06.014. Epub 2017 Jun 9. PubMed PMID: 28606623; PubMed Central PMCID: PMC5558428.

5: Grazioso G, Sgrignani J, Capelli R, Matera C, Dallanoce C, De Amici M, Cavalli A. Allosteric Modulation of Alpha7 Nicotinic Receptors: Mechanistic Insight through Metadynamics and Essential Dynamics. J Chem Inf Model. 2015 Dec 28;55(12):2528-39. doi: 10.1021/acs.jcim.5b00459. Epub 2015 Nov 20. PubMed PMID: 26569022.

6: Thakur GA, Kulkarni AR, Deschamps JR, Papke RL. Expeditious synthesis, enantiomeric resolution, and enantiomer functional characterization of (4-(4-bromophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-sulfonamide (4BP-TQS): an allosteric agonist-positive allosteric modulator of α7 nicotinic acetylcholine receptors. J Med Chem. 2013 Nov 14;56(21):8943-7. doi: 10.1021/jm401267t. Epub 2013 Oct 25. PubMed PMID: 24090443; PubMed Central PMCID: PMC3933094.

7: Horenstein NA, Papke RL, Kulkarni AR, Chaturbhuj GU, Stokes C, Manther K, Thakur GA. Critical Molecular Determinants of α7 Nicotinic Acetylcholine Receptor Allosteric Activation: SEPARATION OF DIRECT ALLOSTERIC ACTIVATION AND POSITIVE ALLOSTERIC MODULATION. J Biol Chem. 2016 Mar 4;291(10):5049-67. doi: 10.1074/jbc.M115.692392. Epub 2016 Jan 7. PubMed PMID: 26742843; PubMed Central PMCID: PMC4777841.