Dihydroxyphenylglycine (anhydrous) | CAS3162870-29-3 | agonist

MedKoo Cat#: 596070 | Name: Dihydroxyphenylglycine

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Description:

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

Dihydroxyphenylglycine is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.

Chemical Structure

Dihydroxyphenylglycine

CAS#162870-29-3

Theoretical Analysis

MedKoo Cat#: 596070

Name: Dihydroxyphenylglycine

CAS#: 162870-29-3

Chemical Formula: C8H9NO4

Exact Mass: 183.0530

Molecular Weight: 183.16

Elemental Analysis: C, 52.46; H, 4.95; N, 7.65; O, 34.94

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Synonym

Dihydroxyphenylglycine; DHPG; S-DHPG; (S)-3,5-DHPG;

IUPAC/Chemical Name

(S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid

InChi Key

HOOWCUZPEFNHDT-ZETCQYMHSA-N

InChi Code

InChI=1S/C8H9NO4/c9-7(8(12)13)4-1-5(10)3-6(11)2-4/h1-3,7,10-11H,9H2,(H,12,13)/t7-/m0/s1

SMILES Code

O=C(O)[C@@H](N)C1=CC(O)=CC(O)=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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

A selective agonist of group I mGluRs.

In vitro activity:

While pressure ejection of the group I mGluR (mGluR1/5) agonist DHPG [(S)-3,5-dihydroxyphenylglycine] equally engages both mGluR1 and mGluR5 subtypes, the mGluR-dependent component of IPSCs elicited by intrastriatal electrical stimulation is almost exclusively mediated by the mGluR1 subtype. Reference: J Neurosci. 2013 Feb 6;33(6):2697-708. https://pubmed.ncbi.nlm.nih.gov/23392696/

In vivo activity:

After treating the astrocytes from the EC and hippocampus of non-Tg and 3xTg-AD mice with 100 nM Aβ1-42 oligomers, cells were loaded with the calcium probe Fluo4-AM, and their responses to 100 nM DHPG (15 s) were analyzed. Figures 3a and b show representative traces of DHPG-induced Ca2+ responses in astrocytes derived from the hippocampus and EC of non-Tg and 3xTg-AD mice. Treatment with Aβ significantly increased the amplitude of DHPG-responses in hippocampal astrocytes when compared with control. Reference: Cell Death Dis. 2013 May 9;4(5):e623. https://pubmed.ncbi.nlm.nih.gov/23661001/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	99.41
	PBS (pH 7.2)	20.0	99.41

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 183.16 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. Clements MA, Swapna I, Morikawa H. Inositol 1,4,5-triphosphate drives glutamatergic and cholinergic inhibition selectively in spiny projection neurons in the striatum. J Neurosci. 2013 Feb 6;33(6):2697-708. doi: 10.1523/JNEUROSCI.4759-12.2013. PMID: 23392696; PMCID: PMC3572919. 2. Durakoglugil MS, Wasser CR, Wong CH, Pohlkamp T, Xian X, Lane-Donovan C, Fritschle K, Naestle L, Herz J. Reelin Regulates Neuronal Excitability through Striatal-Enriched Protein Tyrosine Phosphatase (STEP61) and Calcium Permeable AMPARs in an NMDAR-Dependent Manner. J Neurosci. 2021 Sep 1;41(35):7340-7349. doi: 10.1523/JNEUROSCI.0388-21.2021. Epub 2021 Jul 21. PMID: 34290083; PMCID: PMC8412985. 3. Grolla AA, Sim JA, Lim D, Rodriguez JJ, Genazzani AA, Verkhratsky A. Amyloid-β and Alzheimer's disease type pathology differentially affects the calcium signalling toolkit in astrocytes from different brain regions. Cell Death Dis. 2013 May 9;4(5):e623. doi: 10.1038/cddis.2013.145. PMID: 23661001; PMCID: PMC3674354. 4. Zho WM, You JL, Huang CC, Hsu KS. The group I metabotropic glutamate receptor agonist (S)-3,5-dihydroxyphenylglycine induces a novel form of depotentiation in the CA1 region of the hippocampus. J Neurosci. 2002 Oct 15;22(20):8838-49. doi: 10.1523/JNEUROSCI.22-20-08838.2002. PMID: 12388590; PMCID: PMC6757695.

In vitro protocol:

In vivo protocol:

1. Grolla AA, Sim JA, Lim D, Rodriguez JJ, Genazzani AA, Verkhratsky A. Amyloid-β and Alzheimer's disease type pathology differentially affects the calcium signalling toolkit in astrocytes from different brain regions. Cell Death Dis. 2013 May 9;4(5):e623. doi: 10.1038/cddis.2013.145. PMID: 23661001; PMCID: PMC3674354. 2. Zho WM, You JL, Huang CC, Hsu KS. The group I metabotropic glutamate receptor agonist (S)-3,5-dihydroxyphenylglycine induces a novel form of depotentiation in the CA1 region of the hippocampus. J Neurosci. 2002 Oct 15;22(20):8838-49. doi: 10.1523/JNEUROSCI.22-20-08838.2002. PMID: 12388590; PMCID: PMC6757695.

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