PPDA | CAS#684283-16-7 | NMDA receptor antagonist

MedKoo Cat#: 527840 | Name: PPDA

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Description:

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

PPDA is a subtype-selective NMDA receptor antagonist that preferentially binds to NR2C/NR2D-containing receptors.

Chemical Structure

PPDA

CAS#684283-16-7

Theoretical Analysis

MedKoo Cat#: 527840

Name: PPDA

CAS#: 684283-16-7

Chemical Formula: C21H18N2O5

Exact Mass: 378.1216

Molecular Weight: 378.38

Elemental Analysis: C, 66.66; H, 4.80; N, 7.40; O, 21.14

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 355.00
50mg	USD 1,250.00

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Synonym

PPDA

IUPAC/Chemical Name

(2S*,3R*)-1-(Phenanthren-2-carbonyl)piperazine-2,3-dicarboxylic acid

InChi Key

IWWXIZOMXGOTPP-MSOLQXFVSA-N

InChi Code

InChI=1S/C21H18N2O5/c24-19(23-10-9-22-17(20(25)26)18(23)21(27)28)14-7-8-16-13(11-14)6-5-12-3-1-2-4-15(12)16/h1-8,11,17-18,22H,9-10H2,(H,25,26)(H,27,28)/t17-,18+/m1/s1

SMILES Code

O=C([C@H]1N(C(C2=CC=C3C4=CC=CC=C4C=CC3=C2)=O)CCN[C@H]1C(O)=O)O

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:

PPDA is a subtype-selective NMDA receptor antagonist that preferentially binds to NR2C/NR2D containing receptors.

In vitro activity:

This analysis suggested an affinity order for the PPDA isomers of d-cis > L-cis > L-trans = D-trans and predicted that the 2-position carboxylate group of the cis-PPDA isomers, but not of the trans-PPDA isomers, may be interacting with histidine 486 in NR2B. Consistent with these predictions, cis-PPDA displays a 35-fold higher affinity for NR2B-containing NMDA receptors than trans-PPDA. In addition, mutating NR2B's H486 to phenylalanine decreased cis-PPDA affinity 8-fold but had no effect on trans-PPDA affinity. Reference: J Pharmacol Exp Ther. 2005 Jun;313(3):1066-74. https://pubmed.ncbi.nlm.nih.gov/15743930/

In vivo activity:

In addition, selective inhibition of NR2C/2D-containing NMDARs with PPDA caused a larger decrease on peak amplitude of NMDAR-EPSCs in SNL than that in sham-operated mice. Appling of selective potentiator of NR2C/2D, CIQ, markedly enhanced the evoked NMDAR-EPSCs in SNL-operated mice, but no change in sham-operated mice. Finally, intra-NAc injection of PPDA significantly attenuated SNL-induced mechanical allodynia and depressive-like behavior. Reference: Mol Pain. 2022 Jan-Dec;18:17448069211053255. https://pubmed.ncbi.nlm.nih.gov/35057644/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	37.8	100.00

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 378.38 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. Kinarsky L, Feng B, Skifter DA, Morley RM, Sherman S, Jane DE, Monaghan DT. Identification of subunit- and antagonist-specific amino acid residues in the N-Methyl-D-aspartate receptor glutamate-binding pocket. J Pharmacol Exp Ther. 2005 Jun;313(3):1066-74. doi: 10.1124/jpet.104.082990. Epub 2005 Mar 2. PMID: 15743930. 2. Feng B, Tse HW, Skifter DA, Morley R, Jane DE, Monaghan DT. Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid. Br J Pharmacol. 2004 Feb;141(3):508-16. doi: 10.1038/sj.bjp.0705644. Epub 2004 Jan 12. PMID: 14718249; PMCID: PMC1574223. 3. Jing PB, Chen XH, Lu HJ, Gao YJ, Wu XB. Enhanced function of NR2C/2D-containing NMDA receptor in the nucleus accumbens contributes to peripheral nerve injury-induced neuropathic pain and depression in mice. Mol Pain. 2022 Jan-Dec;18:17448069211053255. doi: 10.1177/17448069211053255. PMID: 35057644; PMCID: PMC8785348.

In vitro protocol:

In vivo protocol:

1. Jing PB, Chen XH, Lu HJ, Gao YJ, Wu XB. Enhanced function of NR2C/2D-containing NMDA receptor in the nucleus accumbens contributes to peripheral nerve injury-induced neuropathic pain and depression in mice. Mol Pain. 2022 Jan-Dec;18:17448069211053255. doi: 10.1177/17448069211053255. PMID: 35057644; PMCID: PMC8785348.

1: Kishimoto S, Matsumoto T, Maruhashi T, Iwamoto Y, Kajikawa M, Oda N, Matsui S, Hashimoto H, Hidaka T, Kihara Y, Chayama K, Goto C, Aibara Y, Yusoff FBM, Nakashima A, Noma K, Higashi Y. Reactive hyperemia-peripheral arterial tonometry is useful for assessment of not only endothelial function but also stenosis of the digital artery. Int J Cardiol. 2018 Jun 1;260:178-183. doi: 10.1016/j.ijcard.2017.10.069. PubMed PMID: 29622435. 2: Targhoo A, Amiri A, Baghayeri M. Magnetic nanoparticles coated with poly(p-phenylenediamine-co-thiophene) as a sorbent for preconcentration of organophosphorus pesticides. Mikrochim Acta. 2017 Dec 5;185(1):15. doi: 10.1007/s00604-017-2560-1. PubMed PMID: 29594381. 3: Zhang X, Zhan Z, Liang X, Chen C, Liu X, Jia Y, Hu M. Lanthanide-MOFs constructed from mixed dicarboxylate ligands as selective multi-responsive luminescent sensors. Dalton Trans. 2018 Mar 6;47(10):3272-3282. doi: 10.1039/c7dt02966g. PubMed PMID: 29431809. 4: Byrne AW, Graham J, Brown C, Donaghy A, Guelbenzu-Gonzalo M, McNair J, Skuce RA, Allen A, McDowell SW. Modelling the variation in skin-test tuberculin reactions, post-mortem lesion counts and case pathology in tuberculosis-exposed cattle: Effects of animal characteristics, histories and co-infection. Transbound Emerg Dis. 2018 Jan 23. doi: 10.1111/tbed.12814. [Epub ahead of print] PubMed PMID: 29363285. 5: Parsons SDC, Morar-Leather D, Buss P, Hofmeyr J, McFadyen R, Rutten VPMG, van Helden PD, Miller MA, Michel AL. The Kinetics of the Humoral and Interferon-Gamma Immune Responses to Experimental Mycobacterium bovis Infection in the White Rhinoceros (Ceratotherium simum). Front Immunol. 2017 Dec 22;8:1831. doi: 10.3389/fimmu.2017.01831. eCollection 2017. PubMed PMID: 29312328; PubMed Central PMCID: PMC5743672. 6: Joharian M, Abedi S, Morsali A. Sonochemical synthesis and structural characterization of a new nanostructured Co(II) supramolecular coordination polymer with Lewis base sites as a new catalyst for Knoevenagel condensation. Ultrason Sonochem. 2017 Nov;39:897-907. doi: 10.1016/j.ultsonch.2017.06.009. Epub 2017 Jun 15. PubMed PMID: 28733021. 7: Lu W, Yang H, Li X, Wang C, Zhan X, Qi D, Bian Y, Jiang J. Chiral Discrimination of Diamines by a Binaphthalene-Bridged Porphyrin Dimer. Inorg Chem. 2017 Jul 17;56(14):8223-8231. doi: 10.1021/acs.inorgchem.7b00920. Epub 2017 Jun 24. PubMed PMID: 28648063. 8: Mikics E, Toth M, Biro L, Bruzsik B, Nagy B, Haller J. The role of GluN2B-containing NMDA receptors in short- and long-term fear recall. Physiol Behav. 2017 Aug 1;177:44-48. doi: 10.1016/j.physbeh.2017.04.005. Epub 2017 Apr 8. PubMed PMID: 28400283. 9: Williams JC, Nguyen BN, McCorkle L, Scheiman D, Griffin JS, Steiner SA 3rd, Meador MA. Highly Porous, Rigid-Rod Polyamide Aerogels with Superior Mechanical Properties and Unusually High Thermal Conductivity. ACS Appl Mater Interfaces. 2017 Jan 18;9(2):1801-1809. doi: 10.1021/acsami.6b13100. Epub 2017 Jan 6. PubMed PMID: 28060486. 10: Xu Z, Xue P, Gao YE, Liu S, Shi X, Hou M, Kang Y. pH-responsive polymeric micelles based on poly(ethyleneglycol)-b-poly(2-(diisopropylamino) ethyl methacrylate) block copolymer for enhanced intracellular release of anticancer drugs. J Colloid Interface Sci. 2017 Mar 15;490:511-519. doi: 10.1016/j.jcis.2016.11.091. Epub 2016 Nov 27. PubMed PMID: 27918989. 11: Shibata E, Takao H, Amemiya S, Ohtomo K. Perioperative Hemodynamic Monitoring of Common Hepatic Artery for Endovascular Embolization of a Pancreaticoduodenal Arcade Aneurysm with Celiac Stenosis. Cardiovasc Intervent Radiol. 2017 Mar;40(3):465-469. doi: 10.1007/s00270-016-1517-9. Epub 2016 Nov 18. PubMed PMID: 27864611. 12: Bhandari D, Ruhl J, Murphy A, McGahee E, Chambers D, Blount BC. Isotope Dilution UPLC-APCI-MS/MS Method for the Quantitative Measurement of Aromatic Diamines in Human Urine: Biomarkers of Diisocyanate Exposure. Anal Chem. 2016 Nov 1;88(21):10687-10692. Epub 2016 Oct 14. PubMed PMID: 27690384; PubMed Central PMCID: PMC5292774. 13: Dong WL, Li SY, Yue JY, Wang C, Wang D, Wan LJ. Fabrication of bilayer tetrathiafulvalene integrated surface covalent organic frameworks. Phys Chem Chem Phys. 2016 Jun 29;18(26):17356-9. doi: 10.1039/c6cp01804a. PubMed PMID: 27314983. 14: Ortiz Salvador JM, Esteve Martínez A, Subiabre Ferrer D, Victoria Martínez AM, de la Cuadra Oyanguren J, Zaragoza Ninet V. [Para-phenylenediamine allergic contact dermatitis due to henna tattoos in a child and adolescent population]. An Pediatr (Barc). 2017 Mar;86(3):122-126. doi: 10.1016/j.anpedi.2016.02.010. Epub 2016 May 9. Spanish. PubMed PMID: 27174179. 15: Hoa le T, Hur SH. Non-Enzymatic Glucose Sensor Based on 3D Graphene Oxide Hydrogel Crosslinked by Various Diamines. J Nanosci Nanotechnol. 2015 Nov;15(11):8697-700. PubMed PMID: 26726578. 16: Muhamadali H, Xu Y, Morra R, Trivedi DK, Rattray NJ, Dixon N, Goodacre R. Metabolomic analysis of riboswitch containing E. coli recombinant expression system. Mol Biosyst. 2016 Feb;12(2):350-61. doi: 10.1039/c5mb00624d. PubMed PMID: 26621574. 17: Shoja Y, Rafati AA, Ghodsi J. Glassy carbon electrode modified with horse radish peroxidase/organic nucleophilic-functionalized carbon nanotube composite for enhanced electrocatalytic oxidation and efficient voltammetric sensing of levodopa. Mater Sci Eng C Mater Biol Appl. 2016 Jan 1;58:835-45. doi: 10.1016/j.msec.2015.09.028. Epub 2015 Sep 11. PubMed PMID: 26478378. 18: Dong WL, Wang L, Ding HM, Zhao L, Wang D, Wang C, Wan LJ. Substrate Orientation Effect in the On-Surface Synthesis of Tetrathiafulvalene-Integrated Single-Layer Covalent Organic Frameworks. Langmuir. 2015 Nov 3;31(43):11755-9. doi: 10.1021/acs.langmuir.5b02412. Epub 2015 Oct 20. PubMed PMID: 26467436. 19: Qi Y, Yang Y. Hunger States Control the Directions of Synaptic Plasticity via Switching Cell Type-Specific Subunits of NMDA Receptors. J Neurosci. 2015 Sep 23;35(38):13171-82. doi: 10.1523/JNEUROSCI.0855-15.2015. PubMed PMID: 26400946. 20: Oikonomou KD, Singh MB, Rich MT, Short SM, Antic SD. Contribution of extrasynaptic N-methyl-D-aspartate and adenosine A1 receptors in the generation of dendritic glutamate-mediated plateau potentials. Philos Trans R Soc Lond B Biol Sci. 2015 Jul 5;370(1672). pii: 20140193. doi: 10.1098/rstb.2014.0193. PubMed PMID: 26009772; PubMed Central PMCID: PMC4455762.