PB-28

PB-28
Names
	IUPAC name 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetra- hydronaphthalen-1-yl)propyl]piperazine
	Other names PB28
Identifiers
CAS Number	dihydrochloride: 172906-90-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:189648;
ChEMBL	ChEMBL53325 ;
ChemSpider	8649746 ;
ECHA InfoCard	100.215.826
IUPHAR/BPS	6681;
MeSH	C097775
PubChem CID	10474335; dihydrochloride: 46861545;
UNII	XTX7Z22467 ;
CompTox Dashboard (EPA)	DTXSID00676880 ;
	InChI InChI=1S/C24H38N2O/c1-27-24-14-6-12-22-20(8-5-13-23(22)24)9-7-15-25-16-18-26(19-17-25)21-10-3-2-4-11-21/h6,12,14,20-21H,2-5,7-11,13,15-19H2,1H3 Key: PHRCDWVPTULQMT-UHFFFAOYSA-N ; InChI=1/C24H38N2O/c1-27-24-14-6-12-22-20(8-5-13-23(22)24)9-7-15-25-16-18-26(19-17-25)21-10-3-2-4-11-21/h6,12,14,20-21H,2-5,7-11,13,15-19H2,1H3 Key: PHRCDWVPTULQMT-UHFFFAOYAW;
	SMILES COc1c(CCCC2CCCN3CCN(C4CCCCC4)CC3)c2ccc1;
Properties
Chemical formula	C24H38N2O
Molar mass	370.57 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

PB-28^[1] is an agonist of the sigma-2 receptor.^[2]^[3]^[4]^[5]^[6]

It is derived from cyclohexylpiperazine.

References

^ Berardi F, Colabufo NA, Giudice G, Perrone R, Tortorella V, Govoni S, Lucchi L (1996). "New sigma and 5-HT1A receptor ligands: omega-(tetralin-1-yl)-n-alkylamine derivatives". J. Med. Chem. 39 (1): 176–82. doi:10.1021/jm950409c. PMID 8568804.
^ Cassano G, Gasparre G, Contino M, Niso M, Berardi F, Perrone R, Colabufo NA (2006). "The sigma-2 receptor agonist PB28 inhibits calcium release from the endoplasmic reticulum of SK-N-SH neuroblastoma cells". Cell Calcium. 40 (1): 23–8. doi:10.1016/j.ceca.2006.03.004. PMID 16687172.
^ Azzariti A, Colabufo NA, Berardi F, Porcelli L, Niso M, Simone GM, Perrone R, Paradiso A (2006). "Cyclohexylpiperazine derivative PB28, a sigma2 agonist and sigma1 antagonist receptor, inhibits cell growth, modulates P-glycoprotein, and synergizes with anthracyclines in breast cancer" (PDF). Mol. Cancer Ther. 5 (7): 1807–16. doi:10.1158/1535-7163.MCT-05-0402. PMID 16891467. S2CID 24267660.
^ Colabufo NA, Berardi F, Abate C, Contino M, Niso M, Perrone R (July 2006). "Is the sigma2 receptor a histone binding protein?". Journal of Medicinal Chemistry. 49 (14): 4153–8. doi:10.1021/jm0600592. PMID 16821775.
^ Berardi F, Abate C, Ferorelli S, Uricchio V, Colabufo NA, Niso M, Perrone R (December 2009). "Exploring the importance of piperazine N-atoms for sigma(2) receptor affinity and activity in a series of analogs of 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28)". Journal of Medicinal Chemistry. 52 (23): 7817–28. doi:10.1021/jm9007505. PMID 19842660.
^ Abate C, Elenewski J, Niso M, Berardi F, Colabufo NA, Azzariti A, Perrone R, Glennon RA (February 2010). "Interaction of the sigma(2) receptor ligand PB28 with the human nucleosome: computational and experimental probes of interaction with the H2A/H2B dimer". ChemMedChem. 5 (2): 268–73. doi:10.1002/cmdc.200900402. PMID 20077462. S2CID 33532349.

External links

PB28+compound at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

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[pmid8568804-1] Berardi F, Colabufo NA, Giudice G, Perrone R, Tortorella V, Govoni S, Lucchi L (1996). "New sigma and 5-HT1A receptor ligands: omega-(tetralin-1-yl)-n-alkylamine derivatives". J. Med. Chem. 39 (1): 176–82. doi:10.1021/jm950409c. PMID 8568804.

[pmid16687172-2] Cassano G, Gasparre G, Contino M, Niso M, Berardi F, Perrone R, Colabufo NA (2006). "The sigma-2 receptor agonist PB28 inhibits calcium release from the endoplasmic reticulum of SK-N-SH neuroblastoma cells". Cell Calcium. 40 (1): 23–8. doi:10.1016/j.ceca.2006.03.004. PMID 16687172.

[pmid16891467-3] Azzariti A, Colabufo NA, Berardi F, Porcelli L, Niso M, Simone GM, Perrone R, Paradiso A (2006). "Cyclohexylpiperazine derivative PB28, a sigma2 agonist and sigma1 antagonist receptor, inhibits cell growth, modulates P-glycoprotein, and synergizes with anthracyclines in breast cancer" (PDF). Mol. Cancer Ther. 5 (7): 1807–16. doi:10.1158/1535-7163.MCT-05-0402. PMID 16891467. S2CID 24267660.

[pmid16821775-4] Colabufo NA, Berardi F, Abate C, Contino M, Niso M, Perrone R (July 2006). "Is the sigma2 receptor a histone binding protein?". Journal of Medicinal Chemistry. 49 (14): 4153–8. doi:10.1021/jm0600592. PMID 16821775.

[pmid19842660-5] Berardi F, Abate C, Ferorelli S, Uricchio V, Colabufo NA, Niso M, Perrone R (December 2009). "Exploring the importance of piperazine N-atoms for sigma(2) receptor affinity and activity in a series of analogs of 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28)". Journal of Medicinal Chemistry. 52 (23): 7817–28. doi:10.1021/jm9007505. PMID 19842660.

[pmid20077462-6] Abate C, Elenewski J, Niso M, Berardi F, Colabufo NA, Azzariti A, Perrone R, Glennon RA (February 2010). "Interaction of the sigma(2) receptor ligand PB28 with the human nucleosome: computational and experimental probes of interaction with the H2A/H2B dimer". ChemMedChem. 5 (2): 268–73. doi:10.1002/cmdc.200900402. PMID 20077462. S2CID 33532349.

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v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators