P7C3 | 301353-96-8 | neuroprotective agent

MedKoo Cat#: 510282 | Name: P7C3

Description:

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

P7C3 is a proneurogenic, neuroprotective agent. P7C3 protects newborn neurons from apoptotic cell death, and promotes neurogenesis in mice and rats in the subgranular zone of the hippocampal dentate gyrus, the site of normal neurogenesis in adult mammals. P7C3 is orally available, nontoxic, stable in mice, rats, and cell culture, and capable of penetrating the blood-brain barrier.

Chemical Structure

P7C3

CAS#301353-96-8

Theoretical Analysis

MedKoo Cat#: 510282

Name: P7C3

CAS#: 301353-96-8

Chemical Formula: C21H18Br2N2O

Exact Mass: 471.9786

Molecular Weight: 474.20

Elemental Analysis: C, 53.19; H, 3.83; Br, 33.70; N, 5.91; O, 3.37

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 weeks
200mg	USD 1,150.00	2 weeks
500mg	USD 1,950.00	2 weeks
1g	USD 3,250.00	2 weeks
2g	USD 4,650.00	2 weeks

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Synonym

P7C3

IUPAC/Chemical Name

1-(3,6-dibromo-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol

InChi Key

FZHHRERIIVOATI-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H18Br2N2O/c22-14-6-8-20-18(10-14)19-11-15(23)7-9-21(19)25(20)13-17(26)12-24-16-4-2-1-3-5-16/h1-11,17,24,26H,12-13H2

SMILES Code

OC(CNC1=CC=CC=C1)CN2C3=C(C4=C2C=CC(Br)=C4)C=C(Br)C=C3

Appearance

white to off-white 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, not in water

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:

P7C3 is an orally bioavailable and blood-brain barrier penetrant aminopropyl carbazole, with neuroprotective effects.

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/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	63.26
	DMSO	51.4	108.30
	Ethanol	10.1	21.30

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 474.20 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. 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. Discovery of a proneurogenic, neuroprotective chemical. Cell. 2010 Jul 9;142(1):39-51. doi: 10.1016/j.cell.2010.06.018. PMID: 20603013; PMCID: PMC2930815.

In vitro protocol:

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. Discovery of a proneurogenic, neuroprotective chemical. Cell. 2010 Jul 9;142(1):39-51. doi: 10.1016/j.cell.2010.06.018. PMID: 20603013; PMCID: PMC2930815.

1: 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. 2014 Apr 22. doi: 10.1038/mp.2014.34. [Epub ahead of print] PubMed PMID: 24751964. 2: 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. 3: Pieper AA, McKnight SL, Ready JM. P7C3 and an unbiased approach to drug discovery for neurodegenerative diseases. Chem Soc Rev. 2014 Feb 11. [Epub ahead of print] PubMed PMID: 24514864. 4: 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. 5: Asai-Coakwell M, March L, Dai XH, Duval M, Lopez I, French CR, Famulski J, De Baere E, Francis PJ, Sundaresan P, SauvÃ© Y, Koenekoop RK, Berry FB, Allison WT, Waskiewicz AJ, Lehmann OJ. Contribution of growth differentiation factor 6-dependent cell survival to early-onset retinal dystrophies. Hum Mol Genet. 2013 Apr 1;22(7):1432-42. doi: 10.1093/hmg/dds560. Epub 2013 Jan 9. PubMed PMID: 23307924. 6: De JesÃºs-CortÃ©s 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. 7: 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. 8: 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. 9: Mahapatra A. A small molecule which protects newborn neurons. ACS Chem Neurosci. 2010 Sep 15;1(9):589. doi: 10.1021/cn1000809. Review. PubMed PMID: 22778848; PubMed Central PMCID: PMC3368691. 10: Saxe JP. Screening: Your brain on drugs. Nat Chem Biol. 2010 Sep;6(9):639-40. doi: 10.1038/nchembio.427. PubMed PMID: 20720548. 11: 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.