GGsTop | CAS#926281-37-0 | GGT inhibitor

MedKoo Cat#: 563173 | Name: GGsTop

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Description:

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

GGsTop, also known as Nahlsgen, is an irreversible γ-glutamyl transpeptidase (GGT) inhibitor.

Chemical Structure

GGsTop

CAS#926281-37-0

Theoretical Analysis

MedKoo Cat#: 563173

Name: GGsTop

CAS#: 926281-37-0

Chemical Formula: C13H18NO7P

Exact Mass: 331.0821

Molecular Weight: 331.26

Elemental Analysis: C, 47.14; H, 5.48; N, 4.23; O, 33.81; P, 9.35

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Synonym

GGsTop; GGs-Top; GGs Top; Nahlsgen;

IUPAC/Chemical Name

2-amino-4-((3-(carboxymethyl)phenoxy)(methoxy)phosphoryl)butanoic acid

InChi Key

NTFPDEDRMYYPAC-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H18NO7P/c1-20-22(19,6-5-11(14)13(17)18)21-10-4-2-3-9(7-10)8-12(15)16/h2-4,7,11H,5-6,8,14H2,1H3,(H,15,16)(H,17,18)

SMILES Code

O=C(O)CC1=CC=CC(OP(OC)(CCC(N)C(O)=O)=O)=C1

Appearance

Solid powder

Purity

>95% (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:

GGsTop (Nahlsgen) is a γ−glutamyl transpeptidase (GGT) inhibitor, with a Ki of 170 μM for Human GGT. GGsTop shows a pKa of 9.71, also exhibits Kons of 150±10 and 51±3 M-1 s-1 against E.coli GGT and human GGT, respectively.

In vitro activity:

GGsTOP was found to facilitate the migration of cells when compared with the control cells (Fig. 4A). Migration of the control cells was slow at 24 h and was not much different at 48 h post-wounding. However, increased cell migration was observed in the GGsTOP group, in which the wounded area was reduced by ~50% at 48 h (Fig. 4B). By contrast, in the presence of NAC, the wound closure stimulated by GGsTOP was completely inhibited at 24 and 48 h post-wounding. Reference: Mol Med Rep. 2016 May;13(5):3813-20. https://pubmed.ncbi.nlm.nih.gov/27035100/

In vivo activity:

From day 7 onward, it was observed that collagen was increased in the GGsTop®-treated group compared with the no-treatment rat group. As shown in Figure 4, on days 7 and 12, the GGsTop®-treated group had a significantly increased collagen concentration in the oral mucosa tissue as compared with the no-treatment group. On day 12, the GGsTop®-treated group approached the value of the control group, and it was confirmed that the ulcer had almost healed in terms of collagen concentration. Reference: In Vivo. 2021 Jan-Feb;35(1):175-180. https://pubmed.ncbi.nlm.nih.gov/33402464/

	Solvent	mg/mL	mM
Solubility
	Water	6.6	20.01

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 331.26 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. Jiang Y, Wang X, Li Y, Mu S, Zhou S, Liu Y, Zhang B. GGsTOP increases migration of human periodontal ligament cells in vitro via reactive oxygen species pathway. Mol Med Rep. 2016 May;13(5):3813-20. doi: 10.3892/mmr.2016.5038. Epub 2016 Mar 21. PMID: 27035100; PMCID: PMC4838071. 2. Takeuchi I, Kawamata R, Makino K. Effects of GGsTop® on Collagen and Glutathione in the Oral Mucosa Using a Rat Model of 5-Fluorouracil-Induced Oral Mucositis. In Vivo. 2021 Jan-Feb;35(1):175-180. doi: 10.21873/invivo.12246. PMID: 33402464; PMCID: PMC7880782. 3. Kubota R, Hayashi N, Kinoshita K, Saito T, Ozaki K, Ueda Y, Tsuchishima M, Tsutsumi M, George J. Inhibition of γ-glutamyltransferase ameliorates ischaemia-reoxygenation tissue damage in rats with hepatic steatosis. Br J Pharmacol. 2020 Nov;177(22):5195-5207. doi: 10.1111/bph.15258. Epub 2020 Oct 19. PMID: 32910829; PMCID: PMC7589019.

In vitro protocol:

In vivo protocol:

1. Takeuchi I, Kawamata R, Makino K. Effects of GGsTop® on Collagen and Glutathione in the Oral Mucosa Using a Rat Model of 5-Fluorouracil-Induced Oral Mucositis. In Vivo. 2021 Jan-Feb;35(1):175-180. doi: 10.21873/invivo.12246. PMID: 33402464; PMCID: PMC7880782. 2. Kubota R, Hayashi N, Kinoshita K, Saito T, Ozaki K, Ueda Y, Tsuchishima M, Tsutsumi M, George J. Inhibition of γ-glutamyltransferase ameliorates ischaemia-reoxygenation tissue damage in rats with hepatic steatosis. Br J Pharmacol. 2020 Nov;177(22):5195-5207. doi: 10.1111/bph.15258. Epub 2020 Oct 19. PMID: 32910829; PMCID: PMC7589019.

1: Olson CA, Vuong HE, Yano JM, Liang QY, Nusbaum DJ, Hsiao EY. The Gut Microbiota Mediates the Anti-Seizure Effects of the Ketogenic Diet. Cell. 2018 Jun 14;173(7):1728-1741.e13. doi: 10.1016/j.cell.2018.04.027. Epub 2018 May 24. PubMed PMID: 29804833; PubMed Central PMCID: PMC6003870. 2: Watanabe B, Tabuchi Y, Wada K, Hiratake J. Synthesis and evaluation of the inhibitory activity of the four stereoisomers of the potent and selective human γ-glutamyl transpeptidase inhibitor GGsTop. Bioorg Med Chem Lett. 2017 Nov 1;27(21):4920-4924. doi: 10.1016/j.bmcl.2017.09.017. Epub 2017 Sep 8. PubMed PMID: 28985998. 3: Kamiyama A, Nakajima M, Han L, Wada K, Mizutani M, Tabuchi Y, Kojima-Yuasa A, Matsui-Yuasa I, Suzuki H, Fukuyama K, Watanabe B, Hiratake J. Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity. Bioorg Med Chem. 2016 Nov 1;24(21):5340-5352. doi: 10.1016/j.bmc.2016.08.050. Epub 2016 Aug 31. PubMed PMID: 27622749. 4: Tamura K, Hayashi N, George J, Toshikuni N, Arisawa T, Hiratake J, Tsuchishima M, Tsutsumi M. GGsTop, a novel and specific γ-glutamyl transpeptidase inhibitor, protects hepatic ischemia-reperfusion injury in rats. Am J Physiol Gastrointest Liver Physiol. 2016 Aug 1;311(2):G305-12. doi: 10.1152/ajpgi.00439.2015. Epub 2016 Jun 30. PubMed PMID: 27365338. 5: Jiang Y, Wang X, Li Y, Mu S, Zhou S, Liu Y, Zhang B. GGsTOP increases migration of human periodontal ligament cells in vitro via reactive oxygen species pathway. Mol Med Rep. 2016 May;13(5):3813-20. doi: 10.3892/mmr.2016.5038. Epub 2016 Mar 21. PubMed PMID: 27035100; PubMed Central PMCID: PMC4838071. 6: Terzyan SS, Burgett AW, Heroux A, Smith CA, Mooers BH, Hanigan MH. Human γ-Glutamyl Transpeptidase 1: STRUCTURES OF THE FREE ENZYME, INHIBITOR-BOUND TETRAHEDRAL TRANSITION STATES, AND GLUTAMATE-BOUND ENZYME REVEAL NOVEL MOVEMENT WITHIN THE ACTIVE SITE DURING CATALYSIS. J Biol Chem. 2015 Jul 10;290(28):17576-86. doi: 10.1074/jbc.M115.659680. Epub 2015 May 26. PubMed PMID: 26013825; PubMed Central PMCID: PMC4498091. 7: Tuzova M, Jean JC, Hughey RP, Brown LA, Cruikshank WW, Hiratake J, Joyce-Brady M. Inhibiting lung lining fluid glutathione metabolism with GGsTop as a novel treatment for asthma. Front Pharmacol. 2014 Jul 31;5:179. doi: 10.3389/fphar.2014.00179. eCollection 2014. PubMed PMID: 25132819; PubMed Central PMCID: PMC4116799. 8: Yamamoto S, Watanabe B, Hiratake J, Tanaka R, Ohkita M, Matsumura Y. Preventive effect of GGsTop, a novel and selective γ-glutamyl transpeptidase inhibitor, on ischemia/reperfusion-induced renal injury in rats. J Pharmacol Exp Ther. 2011 Dec;339(3):945-51. doi: 10.1124/jpet.111.183004. Epub 2011 Sep 21. PubMed PMID: 21937737.