G-15

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

MedKoo CAT#: 407480

CAS#: 1161002-05-6

Description: G-15, also known as GRB-G15, is a cell-permeable non-steroidal antagonist of GPER (Ki = 20 nM).


Price and Availability

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G15 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

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Theoretical Analysis

MedKoo Cat#: 407480
Name: G-15
CAS#: 1161002-05-6
Chemical Formula: C19H16BrNO2
Exact Mass: 369.0364
Molecular Weight: 370.246
Elemental Analysis: C, 61.64; H, 4.36; Br, 21.58; N, 3.78; O, 8.64


Synonym: G-15; G15; G 15; GRB-G15.

IUPAC/Chemical Name: (3aS,4R,9bR)-4-(6-bromo-1,3-benzodioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline

InChi Key: YOLTZIVRJAPVPH-MJLGCCKJSA-N

InChi Code: InChI=1S/C19H16BrNO2/c20-15-9-18-17(22-10-23-18)8-14(15)19-13-6-3-5-11(13)12-4-1-2-7-16(12)21-19/h1-5,7-9,11,13,19,21H,6,10H2/t11-,13-,19+/m0/s1

SMILES Code: BrC1=C([C@@H]2NC3=C(C=CC=C3)[C@@]4([H])[C@]2([H])CC=C4)C=C5OCOC5=C1


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: Imesch P, Samartzis EP, Dedes KJ, Fink D, Fedier A. Histone deacetylase inhibitors down-regulate G-protein-coupled estrogen receptor and the GPER-antagonist G-15 inhibits proliferation in endometriotic cells. Fertil Steril. 2013 Sep;100(3):770-6. doi: 10.1016/j.fertnstert.2013.05.008. Epub 2013 Jun 10. PubMed PMID: 23755949.

2: Tamura T, Noda M, Ozaki M, Maruyama M, Matoba Y, Kumagai T, Sugiyama M. Establishment of an efficient fermentation system of gamma-aminobutyric acid by a lactic acid bacterium, Enterococcus avium G-15, isolated from carrot leaves. Biol Pharm Bull. 2010;33(10):1673-9. PubMed PMID: 20930374.

3: Januskauskas A, Lukoseviciute K, Nagy S, Johannisson A, Rodriguez-Martinez H. Assessment of the efficacy of Sephadex G-15 filtration of bovine spermatozoa for cryopreservation. Theriogenology. 2005 Jan 1;63(1):160-78. PubMed PMID: 15589282.

4: Okada TK, Nakabayashi Y, Miyakoshi M, Inoue M. Potassium and sodium chloride ion pairs are presumed to constitute a complex during elution from a Sephadex G-15 column with sodium phosphate buffer. J Chromatogr A. 2003 Feb 14;987(1-2):49-55. PubMed PMID: 12613796.

5: Hawley WR, Battista C, Divack SR, Morales Núñez NB. The role of estrogen G-protein coupled receptor 30 (GPR30) and sexual experience in sexual incentive motivation in male rats. Physiol Behav. 2017 May 1. pii: S0031-9384(17)30131-2. doi: 10.1016/j.physbeh.2017.05.001. [Epub ahead of print] PubMed PMID: 28472669.

6: Cheng Q, Meng J, Wang XS, Kang WB, Tian Z, Zhang K, Liu G, Zhao JN. G-1 exerts neuroprotective effects through G protein-coupled estrogen receptor 1 following spinal cord injury in mice. Biosci Rep. 2016 Aug 31;36(4). pii: e00373. doi: 10.1042/BSR20160134. Print 2016 Aug. PubMed PMID: 27407175; PubMed Central PMCID: PMC5006313.

7: Gibbs RB, Nelson D, Hammond R. Role of GPR30 in mediating estradiol effects on acetylcholine release in the hippocampus. Horm Behav. 2014 Jul;66(2):339-45. doi: 10.1016/j.yhbeh.2014.06.002. Epub 2014 Jun 11. PubMed PMID: 24928571; PubMed Central PMCID: PMC4131743.

8: Kawamura T, Hirata A, Ohno S, Nomura Y, Nagano T, Nameki N, Yokogawa T, Hori H. Multisite-specific archaeosine tRNA-guanine transglycosylase (ArcTGT) from Thermoplasma acidophilum, a thermo-acidophilic archaeon. Nucleic Acids Res. 2016 Feb 29;44(4):1894-908. doi: 10.1093/nar/gkv1522. Epub 2015 Dec 31. PubMed PMID: 26721388; PubMed Central PMCID: PMC4770233.

9: Kurt AH, Bosnak M, Inan SY, Celik A, Uremis MM. Epileptogenic effects of G protein-coupled estrogen receptor 1 in the rat pentylenetetrazole kindling model of epilepsy. Pharmacol Rep. 2016 Feb;68(1):66-70. doi: 10.1016/j.pharep.2015.07.001. Epub 2015 Jul 17. PubMed PMID: 26721354.

10: Ma HR, Wang J, Chen YF, Chen H, Wang WS, Aisa HA. Icariin and icaritin stimulate the proliferation of SKBr3 cells through the GPER1-mediated modulation of the EGFR-MAPK signaling pathway. Int J Mol Med. 2014 Jun;33(6):1627-34. doi: 10.3892/ijmm.2014.1722. Epub 2014 Apr 3. PubMed PMID: 24718680.

11: Okada TK, Miyakoshi M, Inoue M, Nakabayashi Y, Jisaki F. Differential elution of sodium or potassium dihydrogen- and hydrogenphosphate ions from a sephadex G-15 column with sodium or potassium chloride solution. J Chromatogr A. 2001 Apr 20;914(1-2):175-81. PubMed PMID: 11358211.

12: Broughton BR, Brait VH, Kim HA, Lee S, Chu HX, Gardiner-Mann CV, Guida E, Evans MA, Miller AA, Arumugam TV, Drummond GR, Sobey CG. Sex-dependent effects of G protein-coupled estrogen receptor activity on outcome after ischemic stroke. Stroke. 2014 Mar;45(3):835-41. doi: 10.1161/STROKEAHA.113.001499. Epub 2014 Jan 23. PubMed PMID: 24457292.

13: Mikhaĭlova RV, Logbanok AG, Shishko ZhF, Iasenko MI. [Effect of conditions of culturing Penicillium funiculosum G-15 on production of extracellular glucose oxidase]. Prikl Biokhim Mikrobiol. 2000 Mar-Apr;36(2):199-203. Russian. PubMed PMID: 10780009.

14: Hammond R, Nelson D, Kline E, Gibbs RB. Chronic treatment with a GPR30 antagonist impairs acquisition of a spatial learning task in young female rats. Horm Behav. 2012 Sep;62(4):367-74. doi: 10.1016/j.yhbeh.2012.07.004. Epub 2012 Jul 22. PubMed PMID: 22828404; PubMed Central PMCID: PMC3477261.

15: Okada TK, Nakabayashi Y, Jisaki F. Coupling of chromatographic ion-exchange reaction with change-partner reaction. Presumed mechanism on the ion-ion interaction of inorganic ions in Sephadex G-15 columns. J Chromatogr A. 2000 Feb 11;869(1-2):91-9. PubMed PMID: 10720228.

16: Abu-Ghazalah RM, Irizar J, Helmy AS, Macgregor RB Jr. A study of the interactions that stabilize DNA frayed wires. Biophys Chem. 2010 Apr;147(3):123-9. doi: 10.1016/j.bpc.2010.01.003. Epub 2010 Jan 20. PubMed PMID: 20122787.

17: Tatti S, Stockfleth E, Beutner KR, Tawfik H, Elsasser U, Weyrauch P, Mescheder A. Polyphenon E: a new treatment for external anogenital warts. Br J Dermatol. 2010 Jan;162(1):176-84. doi: 10.1111/j.1365-2133.2009.09375.x. Epub 2009 Jul 27. PubMed PMID: 19709100.

18: Ramió-Lluch L, Balasch S, Bonet S, Briz M, Pinart E, Rodríguez-Gil JE. Effects of filtration through Sephadex columns improve overall quality parameters and "in vivo" fertility of subfertile refrigerated boar-semen. Anim Reprod Sci. 2009 Oct;115(1-4):189-200. doi: 10.1016/j.anireprosci.2008.12.015. Epub 2008 Dec 24. PubMed PMID: 19157731.

19: Méndez-Luna D, Bello M, Correa-Basurto J. Understanding the molecular basis of agonist/antagonist mechanism of GPER1/GPR30 through structural and energetic analyses. J Steroid Biochem Mol Biol. 2016 Apr;158:104-16. doi: 10.1016/j.jsbmb.2016.01.001. Epub 2016 Jan 6. PubMed PMID: 26772481.

20: Kim J, Szinte JS, Boulware MI, Frick KM. 17β-Estradiol and Agonism of G-protein-Coupled Estrogen Receptor Enhance Hippocampal Memory via Different Cell-Signaling Mechanisms. J Neurosci. 2016 Mar 16;36(11):3309-21. doi: 10.1523/JNEUROSCI.0257-15.2016. PubMed PMID: 26985039; PubMed Central PMCID: PMC4792941.