P7C3-OMe
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MedKoo CAT#: 530596

CAS#: 1235481-43-2

Description: P7C3-OMe, also known as (R)-P7C3-OMe, is an analogue of P7C3 and P3C3-A20. P7C3 Attenuates the Scopolamine-Induced Memory Impairments in C57BL/6J Mice.P7C3-A20 promotes neurogenesis and improves cognitive function after ischemic stroke.

Chemical Structure

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P7C3-OMe
CAS# 1235481-43-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530596
Name: P7C3-OMe
CAS#: 1235481-43-2
Chemical Formula: C22H20Br2N2O2
Exact Mass: 501.99
Molecular Weight: 504.222
Elemental Analysis: C, 52.41; H, 4.00; Br, 31.69; N, 5.56; O, 6.35

Price and Availability

Size Price Availability Quantity
100mg USD 850 2 weeks
200mg USD 1450 2 weeks
500mg USD 2250 2 weeks
1g USD 3650 2 weeks
2g USD 4850 2 weeks
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Synonym: P7C3-OMe; (R)-P7C3-OMe

IUPAC/Chemical Name: (2R)-1-(3,6-dibromocarbazol-9-yl)-3-(3-methoxyanilino)propan-2-ol

InChi Key: LEICNUMXFWNCSJ-QGZVFWFLSA-N

InChi Code: InChI=1S/C22H20Br2N2O2/c1-28-18-4-2-3-16(11-18)25-12-17(27)13-26-21-7-5-14(23)9-19(21)20-10-15(24)6-8-22(20)26/h2-11,17,25,27H,12-13H2,1H3/t17-/m1/s1

SMILES Code: O[C@H](CNC1=CC=CC(OC)=C1)CN2C3=C(C4=C2C=CC(Br)=C4)C=C(Br)C=C3

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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: (S)-P7C3-OMe, P7C3-A20 hydroxylated analog, is the (S)-enantiomer of P7C3-OMe. P7C3-OMe is a pro-neurogenic compound.
In vitro activity: This study showed that P7C3 specially suppressed the expression of lipopolysaccharide (LPS)-induced pro-inflammatory factors but not influenced the anti-inflammatory factors in microglia. The inhibition of the nuclear factor κB (NF-κB) signaling pathway was involved in the mechanisms of the anti-inflammatory effects by P7C3. LPS-induced activation of IκB kinase (IKK), degradation of the inhibitory κB alpha (IκBα) and nuclear translocation of NF-κB can be attenuated by the pretreatment of P7C3 in microglia. Furthermore, in LPS-treated microglia, P7C3-pretreatment decreased the toxicity of conditioned media to MES23.5 cells (a dopaminergic (DA) cell line). Reference: Front Cell Neurosci. 2018 Nov 5;12:400. https://pubmed.ncbi.nlm.nih.gov/30455635/
In vivo activity: In vivo studies gave evidence that P7C3 exerts its proneurogenic activity by protecting newborn neurons from apoptosis. Mice missing the gene encoding neuronal PAS domain protein 3 (NPAS3) are devoid of hippocampal neurogenesis and display malformation and electrophysiological dysfunction of the dentate gyrus. Prolonged administration of P7C3 to npas3(-/-) mice corrected these deficits by normalizing levels of apoptosis of newborn hippocampal neurons. Prolonged administration of P7C3 to aged rats also enhanced neurogenesis in the dentate gyrus, impeded neuron death, and preserved cognitive capacity as a function of terminal aging. Reference: Cell. 2010 Jul 9;142(1):39-51. https://pubmed.ncbi.nlm.nih.gov/20603013/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 59.50
Ethanol 1.0 1.98

Preparing Stock Solutions

The following data is based on the product molecular weight 504.22 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. Chen W, Jia W, Wu C, Chen L, Sun K, Wang J, Ding B, Liu N, Xu R. The Neurogenic Compound P7C3 Regulates the Aerobic Glycolysis by Targeting Phosphoglycerate Kinase 1 in Glioma. Front Oncol. 2021 Jun 18;11:644492. doi: 10.3389/fonc.2021.644492. PMID: 34221965; PMCID: PMC8252887. 2. Gu C, Hu Q, Wu J, Mu C, Ren H, Liu CF, Wang G. P7C3 Inhibits LPS-Induced Microglial Activation to Protect Dopaminergic Neurons Against Inflammatory Factor-Induced Cell Death in vitro and in vivo. Front Cell Neurosci. 2018 Nov 5;12:400. doi: 10.3389/fncel.2018.00400. PMID: 30455635; PMCID: PMC6230654. 3. Latchney SE, Jaramillo TC, Rivera PD, Eisch AJ, Powell CM. Chronic P7C3 treatment restores hippocampal neurogenesis in the Ts65Dn mouse model of Down Syndrome [Corrected]. Neurosci Lett. 2015 Mar 30;591:86-92. doi: 10.1016/j.neulet.2015.02.008. Epub 2015 Feb 7. Erratum in: Neurosci Lett. 2015 Jun 15;597():25. PMID: 25668489; PMCID: PMC4363293. 4. Pieper AA, Xie S, Capota E, Estill SJ, Zhong J, Long JM, Becker GL, Huntington P, Goldman SE, Shen CH, Capota M, Britt JK, Kotti T, Ure K, Brat DJ, Williams NS, MacMillan KS, Naidoo J, Melito L, Hsieh J, De Brabander J, Ready JM, McKnight SL.
In vitro protocol: 1. Chen W, Jia W, Wu C, Chen L, Sun K, Wang J, Ding B, Liu N, Xu R. The Neurogenic Compound P7C3 Regulates the Aerobic Glycolysis by Targeting Phosphoglycerate Kinase 1 in Glioma. Front Oncol. 2021 Jun 18;11:644492. doi: 10.3389/fonc.2021.644492. PMID: 34221965; PMCID: PMC8252887. 2. Gu C, Hu Q, Wu J, Mu C, Ren H, Liu CF, Wang G. P7C3 Inhibits LPS-Induced Microglial Activation to Protect Dopaminergic Neurons Against Inflammatory Factor-Induced Cell Death in vitro and in vivo. Front Cell Neurosci. 2018 Nov 5;12:400. doi: 10.3389/fncel.2018.00400. PMID: 30455635; PMCID: PMC6230654.
In vivo protocol: 1. Latchney SE, Jaramillo TC, Rivera PD, Eisch AJ, Powell CM. Chronic P7C3 treatment restores hippocampal neurogenesis in the Ts65Dn mouse model of Down Syndrome [Corrected]. Neurosci Lett. 2015 Mar 30;591:86-92. doi: 10.1016/j.neulet.2015.02.008. Epub 2015 Feb 7. Erratum in: Neurosci Lett. 2015 Jun 15;597():25. PMID: 25668489; PMCID: PMC4363293. 2. Pieper AA, Xie S, Capota E, Estill SJ, Zhong J, Long JM, Becker GL, Huntington P, Goldman SE, Shen CH, Capota M, Britt JK, Kotti T, Ure K, Brat DJ, Williams NS, MacMillan KS, Naidoo J, Melito L, Hsieh J, De Brabander J, Ready JM, McKnight SL.

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1: Oku H, Morishita S, Horie T, Nishikawa Y, Kida T, Mimura M, Kojima S, Ikeda T. Protective effect of P7C3 on retinal ganglion cells from optic nerve injury. Jpn J Ophthalmol. 2017 Mar;61(2):195-203. doi: 10.1007/s10384-016-0493-6. Epub 2016 Dec 28. PubMed PMID: 28032230.

2: Loris ZB, Pieper AA, Dalton Dietrich W. The neuroprotective compound P7C3-A20 promotes neurogenesis and improves cognitive function after ischemic stroke. Exp Neurol. 2017 Apr;290:63-73. doi: 10.1016/j.expneurol.2017.01.006. Epub 2017 Jan 8. PubMed PMID: 28077334.

3: Wang SN, Xu TY, Wang X, Guan YF, Zhang SL, Wang P, Miao CY. Neuroprotective Efficacy of an Aminopropyl Carbazole Derivative P7C3-A20 in Ischemic Stroke. CNS Neurosci Ther. 2016 Sep;22(9):782-8. doi: 10.1111/cns.12576. Epub 2016 Jun 23. PubMed PMID: 27333812.

4: Jiang B, Song L, Huang C, Zhang W. P7C3 Attenuates the Scopolamine-Induced Memory Impairments in C57BL/6J Mice. Neurochem Res. 2016 May;41(5):1010-9. doi: 10.1007/s11064-015-1783-y. Epub 2015 Dec 8. PubMed PMID: 26646000.

5: De Jesús-Cortés H, Miller AD, Britt JK, DeMarco AJ, De Jesús-Cortés M, Stuebing E, Naidoo J, Vázquez-Rosa E, Morlock L, Williams NS, Ready JM, Narayanan NS, Pieper AA. Protective efficacy of P7C3-S243 in the 6-hydroxydopamine model of Parkinson's disease. NPJ Parkinsons Dis. 2015;1. pii: 15010. Epub 2015 May 21. PubMed PMID: 27158662; PubMed Central PMCID: PMC4859442.

6: Walker AK, Rivera PD, Wang Q, Chuang JC, Tran S, Osborne-Lawrence S, Estill SJ, Starwalt R, Huntington P, Morlock L, Naidoo J, Williams NS, Ready JM, Eisch AJ, Pieper AA, Zigman JM. The P7C3 class of neuroprotective compounds exerts antidepressant efficacy in mice by increasing hippocampal neurogenesis. Mol Psychiatry. 2015 Apr;20(4):500-8. doi: 10.1038/mp.2014.34. Epub 2014 Apr 22. PubMed PMID: 24751964; PubMed Central PMCID: PMC4206684.

7: Latchney SE, Jaramillo TC, Rivera PD, Eisch AJ, Powell CM. Chronic P7C3 treatment restores hippocampal neurogenesis in the Ts65Dn mouse model of Down Syndrome [Corrected]. Neurosci Lett. 2015 Mar 30;591:86-92. doi: 10.1016/j.neulet.2015.02.008. Epub 2015 Feb 7. Erratum in: Neurosci Lett. 2015 Jun 15;597():25. PubMed PMID: 25668489; PubMed Central PMCID: PMC4363293.

8: Kemp SW, Szynkaruk M, Stanoulis KN, Wood MD, Liu EH, Willand MP, Morlock L, Naidoo J, Williams NS, Ready JM, Mangano TJ, Beggs S, Salter MW, Gordon T, Pieper AA, Borschel GH. Pharmacologic rescue of motor and sensory function by the neuroprotective compound P7C3 following neonatal nerve injury. Neuroscience. 2015 Jan 22;284:202-16. doi: 10.1016/j.neuroscience.2014.10.005. Epub 2014 Oct 13. PubMed PMID: 25313000.

9: Pieper AA, McKnight SL, Ready JM. P7C3 and an unbiased approach to drug discovery for neurodegenerative diseases. Chem Soc Rev. 2014 Oct 7;43(19):6716-26. doi: 10.1039/c3cs60448a. Review. PubMed PMID: 24514864; PubMed Central PMCID: PMC4237066.

10: Yin TC, Britt JK, De Jesús-Cortés H, Lu Y, Genova RM, Khan MZ, Voorhees JR, Shao J, Katzman AC, Huntington PJ, Wassink C, McDaniel L, Newell EA, Dutca LM, Naidoo J, Cui H, Bassuk AG, Harper MM, McKnight SL, Ready JM, Pieper AA. P7C3 neuroprotective chemicals block axonal degeneration and preserve function after traumatic brain injury. Cell Rep. 2014 Sep 25;8(6):1731-40. doi: 10.1016/j.celrep.2014.08.030. Epub 2014 Sep 15. PubMed PMID: 25220467; PubMed Central PMCID: PMC4206693.

11: Dutca LM, Stasheff SF, Hedberg-Buenz A, Rudd DS, Batra N, Blodi FR, Yorek MS, Yin T, Shankar M, Herlein JA, Naidoo J, Morlock L, Williams N, Kardon RH, Anderson MG, Pieper AA, Harper MM. Early detection of subclinical visual damage after blast-mediated TBI enables prevention of chronic visual deficit by treatment with P7C3-S243. Invest Ophthalmol Vis Sci. 2014 Dec 2;55(12):8330-41. doi: 10.1167/iovs.14-15468. PubMed PMID: 25468886; PubMed Central PMCID: PMC5102342.

12: Wang G, Han T, Nijhawan D, Theodoropoulos P, Naidoo J, Yadavalli S, Mirzaei H, Pieper AA, Ready JM, McKnight SL. P7C3 neuroprotective chemicals function by activating the rate-limiting enzyme in NAD salvage. Cell. 2014 Sep 11;158(6):1324-34. doi: 10.1016/j.cell.2014.07.040. PubMed PMID: 25215490; PubMed Central PMCID: PMC4163014.

13: Naidoo J, De Jesus-Cortes H, Huntington P, Estill S, Morlock LK, Starwalt R, Mangano TJ, Williams NS, Pieper AA, Ready JM. Discovery of a neuroprotective chemical, (S)-N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-6-methoxypyridin-2-amine [(-)-P7C3-S243], with improved druglike properties. J Med Chem. 2014 May 8;57(9):3746-54. doi: 10.1021/jm401919s. Epub 2014 Apr 16. PubMed PMID: 24697290; PubMed Central PMCID: PMC4206694.

14: Blaya MO, Bramlett HM, Naidoo J, Pieper AA, Dietrich WD. Neuroprotective efficacy of a proneurogenic compound after traumatic brain injury. J Neurotrauma. 2014 Mar 1;31(5):476-86. doi: 10.1089/neu.2013.3135. Epub 2013 Dec 19. PubMed PMID: 24070637; PubMed Central PMCID: PMC3934600.

15: De Jesús-Cortés H, Xu P, Drawbridge J, Estill SJ, Huntington P, Tran S, Britt J, Tesla R, Morlock L, Naidoo J, Melito LM, Wang G, Williams NS, Ready JM, McKnight SL, Pieper AA. Neuroprotective efficacy of aminopropyl carbazoles in a mouse model of Parkinson disease. Proc Natl Acad Sci U S A. 2012 Oct 16;109(42):17010-5. doi: 10.1073/pnas.1213956109. Epub 2012 Oct 1. PubMed PMID: 23027934; PubMed Central PMCID: PMC3479520.

16: Tesla R, Wolf HP, Xu P, Drawbridge J, Estill SJ, Huntington P, McDaniel L, Knobbe W, Burket A, Tran S, Starwalt R, Morlock L, Naidoo J, Williams NS, Ready JM, McKnight SL, Pieper AA. Neuroprotective efficacy of aminopropyl carbazoles in a mouse model of amyotrophic lateral sclerosis. Proc Natl Acad Sci U S A. 2012 Oct 16;109(42):17016-21. doi: 10.1073/pnas.1213960109. Epub 2012 Oct 1. PubMed PMID: 23027932; PubMed Central PMCID: PMC3479516.

17: Pieper AA, Xie S, Capota E, Estill SJ, Zhong J, Long JM, Becker GL, Huntington P, Goldman SE, Shen CH, Capota M, Britt JK, Kotti T, Ure K, Brat DJ, Williams NS, MacMillan KS, Naidoo J, Melito L, Hsieh J, De Brabander J, Ready JM, McKnight SL. Discovery of a proneurogenic, neuroprotective chemical. Cell. 2010 Jul 9;142(1):39-51. doi: 10.1016/j.cell.2010.06.018. PubMed PMID: 20603013; PubMed Central PMCID: PMC2930815.

18: Lee AS, De Jesús-Cortés H, Kabir ZD, Knobbe W, Orr M, Burgdorf C, Huntington P, McDaniel L, Britt JK, Hoffmann F, Brat DJ, Rajadhyaksha AM, Pieper AA. The Neuropsychiatric Disease-Associated Gene cacna1c Mediates Survival of Young Hippocampal Neurons. eNeuro. 2016 Mar 31;3(2). pii: ENEURO.0006-16.2016. doi: 10.1523/ENEURO.0006-16.2016. eCollection 2016 Mar-Apr. PubMed PMID: 27066530; PubMed Central PMCID: PMC4819284.

19: De Jesús-Cortés H, Rajadhyaksha AM, Pieper AA. Cacna1c: Protecting young hippocampal neurons in the adult brain. Neurogenesis (Austin). 2016 Sep 2;3(1):e1231160. eCollection 2016. PubMed PMID: 27900342; PubMed Central PMCID: PMC5111576.

20: MacMillan KS, Naidoo J, Liang J, Melito L, Williams NS, Morlock L, Huntington PJ, Estill SJ, Longgood J, Becker GL, McKnight SL, Pieper AA, De Brabander JK, Ready JM. Development of proneurogenic, neuroprotective small molecules. J Am Chem Soc. 2011 Feb 9;133(5):1428-37. doi: 10.1021/ja108211m. Epub 2011 Jan 6. PubMed PMID: 21210688; PubMed Central PMCID: PMC3033481.