PPDA

CAS# 684283-16-7

PPDA

Catalog No. BCC5918----Order now to get a substantial discount!

Product Name & Size Price Stock
PPDA:10mg $171.00 In stock
PPDA:20mg $291.00 In stock
PPDA:50mg $684.00 In stock
PPDA:100mg $1197.00 In stock
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Chemical structure

PPDA

3D structure

Chemical Properties of PPDA

Cas No. 684283-16-7 SDF Download SDF
PubChem ID 20811874 Appearance Powder
Formula C21H18N2O5 M.Wt 378.38
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 50 mM in 2eq. NaOH and to 100 mM in DMSO
Chemical Name (2S,3R)-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid
SMILES C1CN(C(C(N1)C(=O)O)C(=O)O)C(=O)C2=CC3=C(C=C2)C4=CC=CC=C4C=C3
Standard InChIKey IWWXIZOMXGOTPP-MSOLQXFVSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of PPDA

DescriptionSubtype-selective NMDA receptor antagonist that preferentially binds to NR2C/NR2D-containing receptors (Ki values are 0.096, 0.125, 0.31 and 0.55 μM for NR2C, NR2D, NR2B and NR2A subunits respectively).

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Preparing Stock Solutions of PPDA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6428 mL 13.2142 mL 26.4285 mL 52.8569 mL 66.0711 mL
5 mM 0.5286 mL 2.6428 mL 5.2857 mL 10.5714 mL 13.2142 mL
10 mM 0.2643 mL 1.3214 mL 2.6428 mL 5.2857 mL 6.6071 mL
50 mM 0.0529 mL 0.2643 mL 0.5286 mL 1.0571 mL 1.3214 mL
100 mM 0.0264 mL 0.1321 mL 0.2643 mL 0.5286 mL 0.6607 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on PPDA

Development-Dependent Changes in the NR2 Subtype of the N-Methyl-D-Aspartate Receptor in the Suprachiasmatic Nucleus of the Rat.[Pubmed:30654688]

J Biol Rhythms. 2019 Feb;34(1):39-50.

The suprachiasmatic nucleus (SCN) is the main brain clock that regulates circadian rhythms in mammals. The SCN synchronizes to the LD cycle through the retinohypothalamic tract (RHT), which projects to ventral SCN neurons via glutamatergic synapses. Released glutamate activates N-methyl-D-aspartate (NMDA) receptors, which play a critical role in the activation of signaling cascades to enable phase shifts. Previous evidence indicates that presynaptic changes during postnatal development consist of an increase in RHT fibers impinging on SCN neurons between postnatal day (P) 1 to 4 and P15. The aim of this study was to evaluate postsynaptic developmental changes in the NR2 subunits that determine the pharmacological and biophysical properties of the neuronal NMDA receptors in the ventral SCN. To identify the expression of NR2 subtypes, we utilized RT-PCR, immunohistochemical fluorescence, and electrophysiological recordings of synaptic activity. We identified development-dependent changes in NR2A, C, and D subtypes in mRNA and protein expression, whereas NR2B protein was equally present at all analyzed postnatal ages. The NR2A antagonist PEAQX (100 nM) reduced the frequency of NMDA excitatory postsynaptic currents (EPSCs) at P8 significantly more than at P34, but the antagonists for NR2B (3 muM Ro 25-6981) and NR2C/D (150 nM PPDA) did not influence NMDA EPSCs differently at the 2 analyzed postnatal ages. Our results point to P8 as the earliest analyzed postnatal age that shows mRNA and protein expression similar to those found at the juvenile stage P34. Taken together, our findings indicate that postsynaptic development-dependent modifications in the NR2 subtypes of the NMDA receptor could be important for the synchronization of ventral SCN neurons to the LD cycle at adult stages.

Atomic/molecular layer deposition of Cu-organic thin films.[Pubmed:30357190]

Dalton Trans. 2018 Nov 13;47(44):15791-15800.

The gas-phase atomic/molecular layer deposition (ALD/MLD) technique is strongly emerging as a viable approach to fabricate new exciting inorganic-organic hybrid thin-film materials. However, much less effort has been made to develop new precursors specifically intended for ALD/MLD; this applies to both the organic and inorganic precursors, and in the latter case in particular to transition metal precursors. Here we introduce copper bisdimethylaminopropoxide (Cu(dmap)2) as a promising transition metal precursor for ALD/MLD to be combined with a variety of organic precursors with different backbones and functional groups, i.e. hydroquinone (HQ), terephthalic acid (TPA), 4,4'-oxydianiline (ODA), p-phenylenediamine (PPDA) and 1,4-benzenedithiol (BDT). Hybrid Cu-organic thin films were obtained from all five organic precursors with appreciably high growth rates ranging from 1.0 to 2.6 A per cycle. However, the Cu(dmap)2 + HQ process was found to yield hybrid Cu-organic films only at temperatures below 120 degrees C, while at higher temperatures metallic Cu films were obtained. The films were characterized by XRR, GIXRD, FTIR, Raman, XPS and UV-Vis spectroscopy.

Fire safety enhancement of a highly efficient flame retardant poly(phenylphosphoryl phenylenediamine) in biodegradable poly(lactic acid).[Pubmed:30300772]

J Hazard Mater. 2019 Feb 5;363:1-9.

Flame-retarded poly(lactic acid) (PLA) biodegradable materials are viewed as promising as sustainable alternatives to petroleum-based commodity polymers. A new highly efficient flame retardant, poly(phenylphosphoryl phenylenediamine) (PPDA), was synthesized by the condensation of phenylphosphoryl dichloride with p-phenylenediamine and its structure was confirmed by (1)H nulear magnetic resonance and Fourier-transform infrared spectroscopy. When 3 wt% PPDA was incorporated into PLA, the limited oxygen index increased from 20.0% of neat PLA to 25.5% and its UL-94 vertical burning testing achieved V-0 rating. Moreover, the total heat release and peak heat release rate values of PLA/3 wt% PPDA material were decreased from 109.1 MJ/m(2) and 643.7 kW/m(2) of PLA to 98.3 MJ/m(2) and 570.0 kW/m(2), respectively, and the fire performance index increased from 0.081 of PLA to 0.132 m(2) s/kW. The high fire safety of PPDA in PLA is mainly attributed to the combined effects of the phosphorous-containing radical inhibition and inert gases and the barrier action of the formed char layer. The addition of less than 3 wt% PPDA has little influence on the tensile and impact properties of PLA. The flame retardant PLA blends have great application potential in electrical casing, automobile interiors and three-dimensional printing materials.

NMDA Receptors Containing GluN2B/2C/2D Subunits Mediate an Increase in Glutamate Release at Hippocampal CA3-CA1 Synapses.[Pubmed:29916144]

Mol Neurobiol. 2019 Mar;56(3):1694-1706.

NMDA receptors (NMDARs) are involved in synaptic transmission and synaptic plasticity in different brain regions, and they modulate glutamate release at different presynaptic sites. Here, we studied whether non-postsynaptic NMDARs, putatively presynaptic (preNMDARs), are tonically active at hippocampal CA3-CA1 synapses, and if they modulate glutamate release. We found that when postsynaptic NMDARs are blocked by MK801, D-AP5 depresses evoked and spontaneous excitatory synaptic transmission, indicating that preNMDARs are tonically active at CA3-CA1 synapses, facilitating glutamate release. The subunit composition of these NMDARs was determined by studying evoked and spontaneous excitatory synaptic transmission in the presence of Zn(2+), Ro 25-6981, and PPDA, antagonists of NMDARs containing GluN2A, GluN2B, and GluN2C/D, respectively. We found that evoked and spontaneous release decreased when the activity of NMDARs containing GluN2B and GluN2C/D subunits but not GluN2A was impeded. In addition, we found that the increase in glutamate release mediated by these NMDARs requires protein kinase A (PKA) activation. We conclude that preNMDARs that contain GluN2B and GluN2C/2D subunits facilitate glutamate release at hippocampal CA3-CA1 synapses through a mechanism that involves PKA.

Crystal structure of a new mol-ecular salt: 4-amino-benzenaminium 5-carb-oxy-penta-noate.[Pubmed:29850054]

Acta Crystallogr E Crystallogr Commun. 2018 Jan 26;74(Pt 2):201-205.

The asymmetric unit of the title mol-ecular salt (systematic name: 4-amino-anilinium 5-carb-oxy-penta-noate), C6H9N2(+).C6H9O4(-), consists of half a 4-amino-benzenaminium cation (4-ABA) and half a 5-carb-oxy-penta-noate anion (5-CP); the other half of each ion is generated by inversion symmetry. Protonation of p-phenyl-enedi-amine (PPDA) leads to the formation of a 1:1 salt, but scrutiny of the crystal structure reveals that both of the amine groups of PPDA are partially protonated, with a half-occupied H atom. For the 5-CP anion, an H atom is positioned on an inversion center midway between two O atoms of inversion-related 5-CP ions. In the crystal, the 5-CP anions are linked by the O-Hcdots, three dots, centeredO hydrogen bond to form chains propagating along the [1-10] direction. The chains are linked via N-Hcdots, three dots, centeredO and N-Hcdots, three dots, centeredN hydrogen bonds involving the 4-ABA cations, forming a three-dimensional supra-molecular framework. The title salt was also prepared by mechanochemical synthesis using liquid-assisted grinding (LAG). Its PXRD pattern matches that of the simulated pattern of the crystal structure of the title mol-ecular salt.

Reactive hyperemia-peripheral arterial tonometry is useful for assessment of not only endothelial function but also stenosis of the digital artery.[Pubmed:29622435]

Int J Cardiol. 2018 Jun 1;260:178-183.

BACKGROUND: Although reactive hyperemia-peripheral arterial tonometry (RH-PAT) is widely used for assessment of endothelial function, RH index (RHI) cannot be measured in some cases when pulse wave amplitude (PWA) is very low. Decrease in PWA is mainly caused by proper palmar digital artery (PPDA) stenosis. The purpose of this study was to evaluate the relationship between PWA measured by RH-PAT and stenosis of the PPDA measured by digital subtraction angiography and to evaluate the limitation of assessment of endothelial function measured by RHI in patients with PPDA stenosis. METHODS: We measured baseline PWA in 51 fingers including the first to third fingers of both hands in 10 patients who had PPDA stenosis and in 66 fingers that were the first fingers of both hands in 33 subjects who had no PPDA stenosis. Severe stenosis was defined as over 75% by lower percent diameter stenosis between two PPDAs in a finger. RESULTS: PWA was significantly correlated with stenosis of the digital artery (r=-0.55; P<0.0001). A PWV value of 300mV was the optimal cut-off value for severe stenosis (sensitivity, 84.0%; specificity, 88.5%). Log RHI was significantly lower in patients with PPDA stenosis than in subjects without PPDA stenosis (0.33+/-0.27 versus 0.73+/-0.27, P=0.007). CONCLUSIONS: RH-PAT may be useful for assessment of not only endothelial function but also PPDA stenosis. RHI may be underestimated in patients with PPDA stenosis. We should pay attention to low baseline PWA when measuring RHI. CLINICAL TRIAL REGISTRATION INFORMATION: URL for clinical trial: http://UMIN; registration number for clinical trial: UMIN000003409.

Chiral Discrimination of Diamines by a Binaphthalene-Bridged Porphyrin Dimer.[Pubmed:28648063]

Inorg Chem. 2017 Jul 17;56(14):8223-8231.

A pair of 1,1'-binaphthalene-bridged bisporphyrins, (R)- and (S)-H1, were designed to examine their chiral discrimination abilities toward a range of model diamines by using UV-vis absorption, CD, and (1)H NMR spectroscopy with the assistance of DFT molecular modeling. The spectroscopic titrations revealed that (R)-/(S)-H1 could encapsulate (R)-/(S)-DACH and (R)-/(S)-PPDA in the chiral bisporphyrin cavities, leading to the selective formation of sandwich-type 1:1 complexes via dual Zn-N coordination interactions. In particular, the chiral recognition energy (DeltaDeltaG degrees ) toward (R)-/(S)-DACH was evaluated to be -4.02 kJ mol(-1). The binding processes afforded sensitive CD spectral changes in response to the stereostructure of chiral diamines. Remarkable enantiodiscrimination effects were also detected in the NMR titrations of (R)-/(S)-H1, in which the nonequivalent chemical shift (DeltaDeltadelta) can reach up to 0.57 ppm for (R)-/(S)-DACH. However, due to the large steric effect, another chiral diamine ((R)-/(S)-DPEA) could not be sandwiched in the chiral bisporphyrin cavity; therefore, (R)-/(S)-DPEA could hardly be discriminated by (R)-/(S)-H1. The present results demonstrate a chiral bisporphyrin host with integrated CD and NMR chiral sensing functions and also highlight the binding-mode-dependent character of its enantiodiscrimination performance for different chiral guests.

The role of GluN2B-containing NMDA receptors in short- and long-term fear recall.[Pubmed:28400283]

Physiol Behav. 2017 Aug 1;177:44-48.

N-methyl-d-aspartate (NMDA) receptors are crucial synaptic elements in long-term memory formation, including the associative learning of fearful events. Although NMDA blockers were consistently shown to inhibit fear memory acquisition and recall, the clinical use of general NMDA blockers is hampered by their side effects. Recent studies revealed significant heterogeneity in the distribution and neurophysiological characteristics of NMDA receptors with different GluN2 (NR2) subunit composition, which may have differential role in fear learning and recall. To investigate the specific role of NMDA receptor subpopulations with different GluN2 subunit compositions in the formation of lasting traumatic memories, we contrasted the effects of general NMDA receptor blockade with GluN2A-, GluN2B-, and GluN2C/D subunit selective antagonists (MK-801, PEAQX, Ro25-6981, PPDA, respectively). To investigate acute and lasting consequences, behavioral responses were investigated 1 and 28days after fear conditioning. We found that MK-801 (0.05 and 0.1mg/kg) decreased fear recall at both time points. GluN2B receptor subunit blockade produced highly similar effects, albeit efficacy was somewhat smaller 28days after fear conditioning. Unlike MK-801, Ro25-6981 (3 and 10mg/kg) did not affect locomotor activity in the open-field. In contrast, GluN2A and GluN2C/D blockers (6 and 20mg/kg PEAQX; 3 and 10mg/kg PPDA, respectively) had no effect on conditioned fear recall at any time point and dose. This sharp contrast between GluN2B- and other subunit-containing NMDA receptor function indicates that GluN2B receptor subunits are intimately involved in fear memory formation, and may provide a novel pharmacological target in post-traumatic stress disorder or other fear-related disorders.

Identification of subunit- and antagonist-specific amino acid residues in the N-Methyl-D-aspartate receptor glutamate-binding pocket.[Pubmed:15743930]

J Pharmacol Exp Ther. 2005 Jun;313(3):1066-74.

The resolved X-ray crystal structures of the glutamate-binding domain (S1/S2 domains) of the GluR2 and NR1 glutamate receptor subunits were used to model the homologous regions of the N-methyl-D-aspartate (NMDA) receptor's NR2 subunits. To test the predictive value of these models, all four stereoisomers of the antagonist 1-(phenanthren-2-carbonyl) piperazine-2,3-dicarboxylic acid (PPDA) were docked into the NR2B glutamate-binding site model. 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. In contrast, the NR2B H486F mutation increased the affinity of the typical antagonists CGS-19755 [(2R*,4S*)-4-phosphonomethyl-2-piperidine carboxylic acid] and 4-(3-phosphonopropyl) piperidine-2-carboxylic acid. In the NR1-based NR2 models, there were only four subunit-specific amino acid residues exposed to the ligand-binding pocket (and six in the GluR2-based models). These residues are located at the edge of the binding pocket, suggesting that large antagonists may be necessary for subtype specificity. Of these residues, mutational analysis and modeling suggest that A414, R712, and G713 (NR2B numbering) may be especially useful for developing NR2C- and NR2D-selective NMDA receptor antagonists and that residues A414 and T428 may determine subunit variations in agonist affinity.

Synthesis and pharmacology of N1-substituted piperazine-2,3-dicarboxylic acid derivatives acting as NMDA receptor antagonists.[Pubmed:15801853]

J Med Chem. 2005 Apr 7;48(7):2627-37.

The binding site for competitive NMDA receptor antagonists is on the NR2 subunit, of which there are four types (NR2A-D). Typical antagonists such as (R)-AP5 have a subunit selectivity of NR2A > NR2B > NR2C > NR2D. The competitive NMDA receptor antagonist (2R,3S)-(1-biphenylyl-4-carbonyl)piperazine-2,3-dicarboxylic acid (PBPD, 16b) displays an unusual selectivity with improved relative affinity for NR2C and NR2D vs NR2A and NR2B. Analogues of 16b bearing aroyl or aryl substituents attached to the N(1) position of piperazine-2,3-dicarboxylic acid have been synthesized to probe the structural requirements for NR2C/NR2D selectivity. A phenanthrenyl-2-carbonyl analogue, 16e, had >60-fold higher affinity for NR2C and NR2D and showed 3-5-fold selectivity for NR2C/NR2D vs NR2A/NR2B. The phenanthrenyl-3-carbonyl analogue (16f) was less potent but more selective, having 5- and 7-fold selectivity for NR2D vs NR2A and NR2B, respectively. Thus, antagonists bearing bulky hydrophobic residues have a different NR2 subunit selectivity than that of typical antagonists.

Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid.[Pubmed:14718249]

Br J Pharmacol. 2004 Feb;141(3):508-16.

(2S*,3R*)-1-(biphenyl-4-carbonyl)piperazine-2,3-dicarboxylic acid (PBPD) is a moderate affinity, competitive N-methyl-d-aspartate (NMDA) receptor antagonist with an atypical pattern of selectivity among NMDA receptor 2 subunit (NR2) subunits. We now describe the activity of several derivatives of PBPD tested at both rat brain NMDA receptors using l-[3H]-glutamate binding assays and at recombinant receptors expressed in Xenopus oocytes. Substituting various branched ring structures for the biphenyl group of PBPD reduced NMDA receptor activity. However, substituting linearly arranged ring structures - fluorenone or phenanthrene groups - retained or enhanced activity. Relative to PBPD, the phenanthrene derivative (2S*, 3R*)-1-(phenanthrene-2-carbonyl)piperazine-2,3-dicarboxylic acid (PPDA) displayed a 30- to 78-fold increase in affinity for native NMDA receptors. At recombinant receptors, PPDA displayed a 16-fold (NR2B) to 94-fold (NR2C) increase in affinity over PBPD. Replacement of the biphenyl group of PBPD with a 9-oxofluorene ring system resulted in small changes in receptor affinity and subtype selectivity. 2'-Bromo substitution on the biphenyl group of PBPD reduced antagonist affinity 3- to 5-fold at NR2A-, NR2B- and NR2D-containing receptors, but had little effect on NR2C-containing receptors. In contrast, 4'-fluoro substitution of the biphenyl ring of PBPD selectively increased NR2A affinity. The aromatic rings of PBPD and PPDA increase antagonist affinity and appear to interact with a region of the NMDA receptor displaying subunit heterogeneity. PPDA is the most potent and selective NR2C/NR2D-preferring antagonist yet reported and thus may be useful in defining NR2C/NR2D function and developing related antagonists with improved NMDA receptor subtype selectivity. British Journal of Pharmacology (2004) 141, 508-516. doi:10.1038/sj.bjp.0705644

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