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Chemical Properties of 1,3-Dipropyl-8-phenylxanthine

Cas No. 85872-53-3 SDF Download SDF
Chemical Name 8-phenyl-1,3-dipropyl-7H-purine-2,6-dione
SMILES CCCN1C(=O)N(CCC)c2[nH]c(nc2C1=O)c3ccccc3 CCCN1C(=O)N(CCC)c2nc([nH]c2C1=O)c3ccccc3
Standard InChI InChI=1S/C17H20N4O2/c1-3-10-20-15-13(16(22)21(11-4-2)17(20)23)18-14(19-15)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3,(H,18,19)
Formula C17H20N4O2 M.Wt 312.37
Solubility Soluble to 5 mM in ethanol with gentle warming and to 10 mM in DMSO with gentle warming
Storage Store at RT
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.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of 1,3-Dipropyl-8-phenylxanthine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2013 mL 16.0067 mL 32.0133 mL 64.0266 mL 80.0333 mL
5 mM 0.6403 mL 3.2013 mL 6.4027 mL 12.8053 mL 16.0067 mL
10 mM 0.3201 mL 1.6007 mL 3.2013 mL 6.4027 mL 8.0033 mL
50 mM 0.064 mL 0.3201 mL 0.6403 mL 1.2805 mL 1.6007 mL
100 mM 0.032 mL 0.1601 mL 0.3201 mL 0.6403 mL 0.8003 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.

References on 1,3-Dipropyl-8-phenylxanthine

[Selectivity of the action of 1,3-dipropyl-8-phenylxanthine on the purine receptors of the intestines].[Pubmed: 3191974]

In experiments on the isolated ileum of guinea pigs and rats it was shown that 1,3-dipropyl-8-phenylxanthine (DPPX) is a highly potent adenosine antagonist blocking A1-adenosine receptors of the myenteric plexus (pA2 = 7.29 +/- 0.06) and allosterically modulating affinity of A2-receptors of the intestinal smooth muscles to adenosine (pA2 = 6.64 +/- 0.05). DPPX exerted no influence on purinergic (PR2), adrenergic and opiate receptors of the nervous and muscular cells of the intestine. Exceeding the activity of theophylline by 339-87 times, DPPX failed to exert the selective effect on A1- and A2-subtypes of adenosine receptors.

Analogues of 1,3-dipropyl-8-phenylxanthine: enhancement of selectivity at A1-adenosine receptors by aryl substituents.[Pubmed: 3016270]

The effect of a variety of aryl substituents on the potency and selectivity of 19 analogues of 1,3-dipropyl-8-phenylxanthine as antagonists at A1- and A2-adenosine receptors in brain tissue was determined. The 4-sulfamoylphenyl and 4-carbamoylphenyl analogues are potent and somewhat selective for the A1 receptor. None of the dihydroxyphenyl analogues are remarkably potent, but all are selective for the A1 receptor. 1,3-Dipropyl-8-(2-hydroxy-4-methoxyphenyl)xanthine is the most selective A1 antagonist of the analogues with a A1/A2 potency ratio of about 90.

[3H]xanthine amine congener of 1,3-dipropyl-8-phenylxanthine: an antagonist radioligand for adenosine receptors.[Pubmed: 3012550]

An amine-functionalized derivative of 1,3-dipropyl-8-phenylxanthine has been prepared in tritiated form as a xanthine amine congener ([3H]XAC) for use as an antagonist radioligand for adenosine receptors. [3H]XAC has higher receptor affinity, higher specific activity, lower nonspecific membrane binding, and more favorable hydrophilicity than 1,3-diethyl-8-[3H]phenylxanthine, the xanthine commonly used for adenosine receptor binding. In rat cerebral cortical membranes, [3H]XAC exhibits saturable, specific binding with a Kd of 1.23 nM and a Bmax of 580 fmol/mg of protein at 37 degrees C. N6-(R-Phenylisopropyl)adenosine is a more potent inhibitor of [3H]XAC binding than is 5'-N-ethylcarboxamidoadenosine, indicating that binding is to an A1-adenosine receptor. In the absence of GTP, the inhibition curves for adenosine agonists versus [3H]XAC binding are biphasic, indicating that [3H]XAC is binding to low- and high-affinity agonist states of the A1 receptor. In the presence of GTP, adenosine analogs exhibit monophasic, low-affinity inhibition of binding of [3H]XAC. Inhibition of [3H]XAC binding by theophylline or by various 8-phenylxanthines is monophasic, and the potencies are commensurate with the potencies of these xanthines as adenosine receptor antagonists. The receptor sites in calf brain membranes exhibit a higher affinity (Kd = 0.17 nM) for [3H]XAC, whereas sites in guinea pig exhibit a slightly lower affinity (Kd = 3.0 nM). Densities of [3H]XAC binding sites are similar in brain membranes from all species.

A [3H]amine congener of 1,3-dipropyl-8-phenylxanthine. A new radioligand for A2 adenosine receptors of human platelets.[Pubmed: 3009222]

A xanthine amine congener (XAC), an amine-functionalized derivative of 1,3-dipropyl-8-phenylxanthine, is an antagonist ligand for A2 adenosine receptors of human platelets. XAC inhibited 5'-N-ethylcarboxamidoadenosine (NECA)-induced stimulation of adenylate cyclase activity with a KB of 24 nM. [3H]XAC exhibits saturable, specific binding with a Kd of 12 nM and a Bmax of 1.1 pmol/mg protein at 37 degrees C. [3H]XAC binding in platelets is the first example of labeling of A2 adenosine receptors in which the potencies of adenosine agonists and antagonists in inhibiting binding are commensurate with their potencies at these receptors in functional studies. Furthermore, [3H]XAC is the first antagonist radioligand with high affinity at A2 adenosine receptors.


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