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MedKoo Cat#: 563604 | Name: Ogerin
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Description:

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

Ogerin is a selective GPR68 agonist, suppressing recall in fear conditioning in wild-type but not in GPR68-knockout mice. Ogerin induces PKA dependent CREB phosphorylation, a marker of Galphas pathway activation.

Chemical Structure

Ogerin
Ogerin
CAS#1309198-71-7

Theoretical Analysis

MedKoo Cat#: 563604

Name: Ogerin

CAS#: 1309198-71-7

Chemical Formula: C17H17N5O

Exact Mass: 307.1433

Molecular Weight: 307.36

Elemental Analysis: C, 66.43; H, 5.58; N, 22.79; O, 5.21

Price and Availability

Size Price Availability Quantity
5mg USD 450.00
25mg USD 875.00
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Related CAS #
No Data
Synonym
Ogerin; ZINC67740571; ZINC-67740571; ZINC 67740571;
IUPAC/Chemical Name
{2-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]phenyl}methanol
InChi Key
MDGIEDNDSFMSLP-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H17N5O/c18-16-20-15(14-9-5-4-8-13(14)11-23)21-17(22-16)19-10-12-6-2-1-3-7-12/h1-9,23H,10-11H2,(H3,18,19,20,21,22)
SMILES Code
OCC1=CC=CC=C1C2=NC(N)=NC(NCC3=CC=CC=C3)=N2
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
>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:
Ogerin is a selective GPR68 positive aliasing modulator (PAM) (pEC50=6.83) with a moderate antagonistic effect on A2A (Ki=220 nM).
In vitro activity:
Ogerin is a positive allosteric modulator (PAM) of GPR68, inducing a leftward shift of the dose response curve to proton induced signaling. Using PHLFs derived from patients with both non-fibrotic and IPF diagnoses, this study shows that Ogerin inhibits, and partially reverses TGF-β induced myofibroblast differentiation in a dose dependent manner. This occurs at the transcriptional level without inhibition of canonical TGF-β induced SMAD signaling. Ogerin induces PKA dependent CREB phosphorylation, a marker of Gαs pathway activation. The ability of Ogerin to inhibit both basal and TGF-β induced collagen gene transcription, and induction of Gαs signaling is enhanced at an acidic pH (pH 6.8). Reference: PLoS One. 2022 Jul 28;17(7):e0271608. https://pubmed.ncbi.nlm.nih.gov/35901086/
In vivo activity:
In WT mice, ogerin attenuated contextual-based fear memory without effects on cue-based memory (Figure 4c–d). Crucially, administration of ogerin had no effect on memory retrieval in GPR68 KO mice (Figure 4c–d), indicating that ogerin’s in vivo effects are GPR68-dependent. Furthermore, the less active ogerin isomer, ZINC32547799, had no measurable effect on learning and memory in wild-type mice (Figure 4c–d and Extended Data Fig 8d–h). Ogerin’s effects thus support a role for GPR68 in hippocampal-associated memory. Reference: Nature. 2015 Nov 26;527(7579):477-83. https://pubmed.ncbi.nlm.nih.gov/26550826/
Solvent mg/mL mM
Solubility
DMSO 110.2 358.68
Ethanol 6.2 20.00
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 307.36 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.

Recalculate based on batch purity %
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. Greenwald E, Posner C, Bharath A, Lyons A, Salmerón C, Sriram K, Wiley SZ, Insel PA, Zhang J. GPCR Signaling Measurement and Drug Profiling with an Automated Live-Cell Microscopy System. ACS Sens. 2023 Jan 27;8(1):19-27. doi: 10.1021/acssensors.2c01341. Epub 2023 Jan 5. PMID: 36602887; PMCID: PMC9994309. 2. Bell TJ, Nagel DJ, Woeller CF, Kottmann RM. Ogerin mediated inhibition of TGF-β(1) induced myofibroblast differentiation is potentiated by acidic pH. PLoS One. 2022 Jul 28;17(7):e0271608. doi: 10.1371/journal.pone.0271608. PMID: 35901086; PMCID: PMC9333254. 3. Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PMID: 26550826; PMCID: PMC4796946.
In vitro protocol:
1. Greenwald E, Posner C, Bharath A, Lyons A, Salmerón C, Sriram K, Wiley SZ, Insel PA, Zhang J. GPCR Signaling Measurement and Drug Profiling with an Automated Live-Cell Microscopy System. ACS Sens. 2023 Jan 27;8(1):19-27. doi: 10.1021/acssensors.2c01341. Epub 2023 Jan 5. PMID: 36602887; PMCID: PMC9994309. 2. Bell TJ, Nagel DJ, Woeller CF, Kottmann RM. Ogerin mediated inhibition of TGF-β(1) induced myofibroblast differentiation is potentiated by acidic pH. PLoS One. 2022 Jul 28;17(7):e0271608. doi: 10.1371/journal.pone.0271608. PMID: 35901086; PMCID: PMC9333254.
In vivo protocol:
1. Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PMID: 26550826; PMCID: PMC4796946.
1: Mazuelas H, Magallón-Lorenz M, Uriarte-Arrazola I, Negro A, Rosas I, Blanco I, Castellanos E, Lázaro C, Gel B, Carrió M, Serra E. Unbalancing cAMP and Ras/MAPK pathways as a therapeutic strategy for cutaneous neurofibromas. JCI Insight. 2024 Jan 4;9(3):e168826. doi: 10.1172/jci.insight.168826. PMID: 38175707; PMCID: PMC11143965. 2: Khan NM, Diaz-Hernandez ME, Martin WN, Patel B, Chihab S, Drissi H. pH- sensing G protein-coupled orphan receptor GPR68 is expressed in human cartilage and correlates with degradation of extracellular matrix during OA progression. PeerJ. 2023 Dec 5;11:e16553. doi: 10.7717/peerj.16553. PMID: 38077417; PMCID: PMC10704986. 3: Greenwald E, Posner C, Bharath A, Lyons A, Salmerón C, Sriram K, Wiley SZ, Insel PA, Zhang J. GPCR Signaling Measurement and Drug Profiling with an Automated Live-Cell Microscopy System. ACS Sens. 2023 Jan 27;8(1):19-27. doi: 10.1021/acssensors.2c01341. Epub 2023 Jan 5. PMID: 36602887; PMCID: PMC9994309. 4: Bell TJ, Nagel DJ, Woeller CF, Kottmann RM. Ogerin mediated inhibition of TGF-β(1) induced myofibroblast differentiation is potentiated by acidic pH. PLoS One. 2022 Jul 28;17(7):e0271608. doi: 10.1371/journal.pone.0271608. PMID: 35901086; PMCID: PMC9333254. 5: Ozkan AD, Gettas T, Sogata A, Phaychanpheng W, Zhou M, Lacroix JJ. Mechanical and chemical activation of GPR68 probed with a genetically encoded fluorescent reporter. J Cell Sci. 2021 Aug 15;134(16):jcs255455. doi: 10.1242/jcs.255455. Epub 2021 Aug 17. PMID: 34322699; PMCID: PMC8435289. 6: Huang XP, Kenakin TP, Gu S, Shoichet BK, Roth BL. Differential Roles of Extracellular Histidine Residues of GPR68 for Proton-Sensing and Allosteric Modulation by Divalent Metal Ions. Biochemistry. 2020 Sep 29;59(38):3594-3614. doi: 10.1021/acs.biochem.0c00576. Epub 2020 Sep 10. PMID: 32865988; PMCID: PMC7872588. 7: Murakami S, Mochimaru Y, Musha S, Kojima R, Deai M, Mogi C, Sato K, Okajima F, Tomura H. Species-Dependent Enhancement of Ovarian Cancer G Protein-Coupled Receptor 1 Activation by Ogerin. Zoolog Sci. 2020 Apr;37(2):103-108. doi: 10.2108/zs190106. PMID: 32282140. 8: Yu X, Huang XP, Kenakin TP, Slocum ST, Chen X, Martini ML, Liu J, Jin J. Design, Synthesis, and Characterization of Ogerin-Based Positive Allosteric Modulators for G Protein-Coupled Receptor 68 (GPR68). J Med Chem. 2019 Aug 22;62(16):7557-7574. doi: 10.1021/acs.jmedchem.9b00869. Epub 2019 Aug 1. PMID: 31298539; PMCID: PMC6923801. 9: McAleer JP, Fan J, Roar B, Primerano DA, Denvir J. Cytokine Regulation in Human CD4 T Cells by the Aryl Hydrocarbon Receptor and Gq-Coupled Receptors. Sci Rep. 2018 Jul 19;8(1):10954. doi: 10.1038/s41598-018-29262-4. PMID: 30026493; PMCID: PMC6053392. 10: Huang XP, Karpiak J, Kroeze WK, Zhu H, Chen X, Moy SS, Saddoris KA, Nikolova VD, Farrell MS, Wang S, Mangano TJ, Deshpande DA, Jiang A, Penn RB, Jin J, Koller BH, Kenakin T, Shoichet BK, Roth BL. Allosteric ligands for the pharmacologically dark receptors GPR68 and GPR65. Nature. 2015 Nov 26;527(7579):477-83. doi: 10.1038/nature15699. Epub 2015 Nov 9. PMID: 26550826; PMCID: PMC4796946.