WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 556337
CAS#: 201216-39-9 (maleate)
Description: 4-PPBP is a σ ligand and selective non-competitive antagonist at recombinant NR1a/2B NMDA receptors expressed in Xenopus oocytes. 4-PPBP protects against newborn excitotoxic brain injury by stabilizing the mitochondrial membrane potential in vitro and inhibiting microglial activation in vivo. 4-PPBP modulates neuronal nitric oxide synthase/postsynaptic density-95 coupling mechanisms and protects against neonatal ischemic degeneration of striatal neurons.
MedKoo Cat#: 556337
Name: 4-PPBP maleate
CAS#: 201216-39-9 (maleate)
Chemical Formula: C25H31NO4
Exact Mass:
Molecular Weight: 409.526
Elemental Analysis: C, 73.32; H, 7.63; N, 3.42; O, 15.63
Related CAS #: 201216-39-9 (maleate) 136534-70-8 (free base)
Synonym: 4-PPBP maleate
IUPAC/Chemical Name: 4-Phenyl-1-(4-phenylbutyl)piperidine maleate
InChi Key: OASPNIMFGJVLES-BTJKTKAUSA-N
InChi Code: InChI=1S/C21H27N.C4H4O4/c1-3-9-19(10-4-1)11-7-8-16-22-17-14-21(15-18-22)20-12-5-2-6-13-20;5-3(6)1-2-4(7)8/h1-6,9-10,12-13,21H,7-8,11,14-18H2;1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code: O=C(O)/C=C\C(O)=O.N1(CCCCC2=CC=CC=C2)CCC(C3=CC=CC=C3)CC1
Appearance: To be determined
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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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
The following data is based on the product molecular weight 409.526 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 |
1: Shen H, Tarafder S, Park G, Qiu J, Xia Y, Lee CH, Gelberman RH, Thomopoulos S. The use of connective tissue growth factor mimics for flexor tendon repair. J Orthop Res. 2022 Dec;40(12):2754-2762. doi: 10.1002/jor.25301. Epub 2022 Feb 25. PMID: 35212415; PMCID: PMC9402796.
2: Park GY, Tarafder S, Eyen SL, Park S, Kim R, Siddiqui Z, Kumar V, Lee CH. Oxo-M and 4-PPBP Delivery via Multi-Domain Peptide Hydrogel Toward Tendon Regeneration. Front Bioeng Biotechnol. 2022 Jan 27;10:773004. doi: 10.3389/fbioe.2022.773004. PMID: 35155388; PMCID: PMC8829701.
3: Dalwadi DA, Kim S, Schetz J, Schreihofer DA, Kim S. Brain-derived neurotrophic factor for high-throughput evaluation of selective Sigma-1 receptor ligands. J Pharmacol Toxicol Methods. 2022 Jan-Feb;113:107129. doi: 10.1016/j.vascn.2021.107129. Epub 2021 Oct 20. PMID: 34678430; PMCID: PMC9358981.
4: Tarafder S, Ricupero C, Minhas S, Yu RJ, Alex AD, Lee CH. A Combination of Oxo-M and 4-PPBP as a potential regenerative therapeutics for tendon injury. Theranostics. 2019 May 31;9(14):4241-4254. doi: 10.7150/thno.35285. PMID: 31281545; PMCID: PMC6592164.
5: Yano H, Bonifazi A, Xu M, Guthrie DA, Schneck SN, Abramyan AM, Fant AD, Hong WC, Newman AH, Shi L. Pharmacological profiling of sigma 1 receptor ligands by novel receptor homomer assays. Neuropharmacology. 2018 May 1;133:264-275. doi: 10.1016/j.neuropharm.2018.01.042. Epub 2018 Jan 31. PMID: 29407216; PMCID: PMC5858991.
6: Dalwadi DA, Kim S, Schetz JA. Activation of the sigma-1 receptor by haloperidol metabolites facilitates brain-derived neurotrophic factor secretion from human astroglia. Neurochem Int. 2017 May;105:21-31. doi: 10.1016/j.neuint.2017.02.003. Epub 2017 Feb 8. PMID: 28188803; PMCID: PMC5375023.
7: Ehlken C, Grundel B, Michels D, Junker B, Stahl A, Schlunck G, Hansen LL, Feltgen N, Martin G, Agostini HT, Pielen A. Increased expression of angiogenic and inflammatory proteins in the vitreous of patients with ischemic central retinal vein occlusion. PLoS One. 2015 May 15;10(5):e0126859. doi: 10.1371/journal.pone.0126859. PMID: 25978399; PMCID: PMC4433200.
8: Hashimoto K. Targeting the sigma-1 receptor chaperone in the treatment of perinatal brain injury. Exp Neurol. 2015 Mar;265:118-21. doi: 10.1016/j.expneurol.2014.12.019. Epub 2015 Jan 10. PMID: 25585013.
9: Wegleiter K, Hermann M, Posod A, Wechselberger K, Stanika RI, Obermair GJ, Kiechl-Kohlendorfer U, Urbanek M, Griesmaier E. The sigma-1 receptor agonist 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP) protects against newborn excitotoxic brain injury by stabilizing the mitochondrial membrane potential in vitro and inhibiting microglial activation in vivo. Exp Neurol. 2014 Nov;261:501-9. doi: 10.1016/j.expneurol.2014.07.022. Epub 2014 Aug 8. PMID: 25111531.
10: Banister SD, Manoli M, Barron ML, Werry EL, Kassiou M. N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects. Bioorg Med Chem. 2013 Oct 1;21(19):6038-52. doi: 10.1016/j.bmc.2013.07.045. Epub 2013 Aug 6. PMID: 23981939.
11: Zhang Y, Shi Y, Qiao L, Sun Y, Ding W, Zhang H, Li N, Chen D. Sigma-1 receptor agonists provide neuroprotection against gp120 via a change in bcl-2 expression in mouse neuronal cultures. Brain Res. 2012 Jan 11;1431:13-22. doi: 10.1016/j.brainres.2011.10.053. Epub 2011 Nov 6. PMID: 22133307.
12: Tan F, Guio-Aguilar PL, Downes C, Zhang M, O'Donovan L, Callaway JK, Crack PJ. The σ 1 receptor agonist 4-PPBP elicits ERK1/2 phosphorylation in primary neurons: a possible mechanism of neuroprotective action. Neuropharmacology. 2010 Nov;59(6):416-24. doi: 10.1016/j.neuropharm.2010.05.014. Epub 2010 Jun 9. PMID: 20538010.
13: Yang ZJ, Carter EL, Torbey MT, Martin LJ, Koehler RC. Sigma receptor ligand 4-phenyl-1-(4-phenylbutyl)-piperidine modulates neuronal nitric oxide synthase/postsynaptic density-95 coupling mechanisms and protects against neonatal ischemic degeneration of striatal neurons. Exp Neurol. 2010 Jan;221(1):166-74. doi: 10.1016/j.expneurol.2009.10.019. Epub 2009 Oct 31. PMID: 19883643; PMCID: PMC2812675.
14: Yang S, Alkayed NJ, Hurn PD, Kirsch JR. Cyclic adenosine monophosphate response element-binding protein phosphorylation and neuroprotection by 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP). Anesth Analg. 2009 Mar;108(3):964-70. doi: 10.1213/ane.0b013e318192442c. PMID: 19224810; PMCID: PMC2828492.
15: Nishimura T, Ishima T, Iyo M, Hashimoto K. Potentiation of nerve growth factor-induced neurite outgrowth by fluvoxamine: role of sigma-1 receptors, IP3 receptors and cellular signaling pathways. PLoS One. 2008 Jul 2;3(7):e2558. doi: 10.1371/journal.pone.0002558. PMID: 18596927; PMCID: PMC2435603.
16: Schetz JA, Perez E, Liu R, Chen S, Lee I, Simpkins JW. A prototypical Sigma-1 receptor antagonist protects against brain ischemia. Brain Res. 2007 Nov 21;1181:1-9. doi: 10.1016/j.brainres.2007.08.068. Epub 2007 Sep 12. PMID: 17919467; PMCID: PMC4896215.
17: Yang S, Bhardwaj A, Cheng J, Alkayed NJ, Hurn PD, Kirsch JR. Sigma receptor agonists provide neuroprotection in vitro by preserving bcl-2. Anesth Analg. 2007 May;104(5):1179-84, tables of contents. doi: 10.1213/01.ane.0000260267.71185.73. PMID: 17456670; PMCID: PMC2596726.
18: Goyagi T, Bhardwaj A, Koehler RC, Traystman RJ, Hurn PD, Kirsch JR. Potent sigma 1-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine provides ischemic neuroprotection without altering dopamine accumulation in vivo in rats. Anesth Analg. 2003 Feb;96(2):532-8, table of contents. doi: 10.1097/00000539-200302000-00043. PMID: 12538208.
19: Goyagi T, Goto S, Bhardwaj A, Dawson VL, Hurn PD, Kirsch JR. Neuroprotective effect of sigma(1)-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine (PPBP) is linked to reduced neuronal nitric oxide production. Stroke. 2001 Jul;32(7):1613-20. doi: 10.1161/01.str.32.7.1613. PMID: 11441209.
20: Harukuni I, Bhardwaj A, Shaivitz AB, DeVries AC, London ED, Hurn PD, Traystman RJ, Kirsch JR, Faraci FM. sigma(1)-receptor ligand 4-phenyl-1-(4-phenylbutyl)-piperidine affords neuroprotection from focal ischemia with prolonged reperfusion. Stroke. 2000 Apr;31(4):976-82. doi: 10.1161/01.str.31.4.976. PMID: 10754008.
