Dipropilciklopentilksantin

Dipropilciklopentilksantin
IUPAC ime
	8-ciklopentil-1,3-dipropil-7H-purin-2,6-dion
Pravni status
Pravni status	Uncontrolled;
Identifikatori
CAS broj	102146-07-6
ATC kod	none
PubChem	CID 1329
IUPHAR/BPS	386
ChemSpider	1289
ChEMBL	CHEMBL183
Hemijski podaci
Formula	C16H24N4O2
Molarna masa	304,386 g/mol
	SMILES C3CCCC3c(nc2c1=O)nc2n(CCC)c(=O)n1CCC; ;
	InChI InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18) ; Key:FFBDFADSZUINTG-UHFFFAOYSA-N ;
Fizički podaci
Tačka topljenja	191 to 194 °C (376 to 381 °F)

8-Ciklopentil-1,3-dipropilksantin (DPCPX, PD-116,948) je lek koji deluje kao potentan i selektivan antagonist adenozinskog A₁ receptora.^[1]^[2] On je visoko selektivan za A₁ u odnosu na druge tipove adenozinskog receptora, ali poput drugih derivata ksantina on takođe deluje kao inhibitor fosfodiesteraze, i skoro je jednako potentan kao i rolipram u inhibiranju PDE4.^[3] On se koristi za studiranje funkcije adenozinskog A₁ receptora kod životinja.^[4]^[5] Utvrđeno je da učestvuje u više važnih funkcija kao što su regulacija disanja^[6] i da je aktivan u različitim regionima mozga.^[7]^[8] Za DPCPX je takođe pokazano da proizvodi bihaviouralne efekte, kao što je povišenje halucinogenih odgovora proizvedenih dejstvom 5-HT_2A agonista DOI,^[9] i otpuštanje dopamina indukovanog MDMA-om,^[10] kao i da formira interakcije sa brojnim antikonvulzivnim lekovima.^[11]^[12]

Reference уреди

^ Martinson EA, Johnson RA, Wells JN (1987). „Potent adenosine receptor antagonists that are selective for the A1 receptor subtype”. Molecular Pharmacology. 31 (3): 247—52. PMID 3561384. ^{[мртва веза]}
^ Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA (1987). „8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors”. Naunyn-Schmiedeberg's Archives of Pharmacology. 336 (2): 204—10. PMID 2825043. doi:10.1007/BF00165806.
^ Ukena D, Schudt C, Sybrecht GW (1993). „Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes”. Biochemical Pharmacology. 45 (4): 847—51. PMID 7680859. doi:10.1016/0006-2952(93)90168-V.
^ Coates J, Sheehan MJ, Strong P (1994). „1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?”. General Pharmacology. 25 (3): 387—94. PMID 7926579.
^ Moro S, Gao ZG, Jacobson KA, Spalluto G (2006). „Progress in the pursuit of therapeutic adenosine receptor antagonists”. Medicinal Research Reviews. 26 (2): 131—59. PMID 16380972. doi:10.1002/med.20048.
^ Vandam RJ, Shields EJ, Kelty JD (2008). „Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation”. BMC Neuroscience. 9: 95. PMC 2567986  . PMID 18826652. doi:10.1186/1471-2202-9-95.
^ Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K (2008). „Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways”. Journal of Neuroscience Research. 86 (13): 2820—8. PMID 18618669. doi:10.1002/jnr.21742.
^ Wu C, Wong T, Wu X, Sheppy E, Zhang L (2009). „Adenosine as an endogenous regulating factor of hippocampal sharp waves”. Hippocampus. 19 (2): 205—20. PMID 18785213. doi:10.1002/hipo.20497.
^ Marek GJ (2009). „Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats”. Neuropharmacology. 56 (8): 1082—7. PMC 2706691  . PMID 19324062. doi:10.1016/j.neuropharm.2009.03.005.
^ Vanattou-Saïfoudine N, Gossen A, Harkin A (2011). „A role for adenosine A(1) receptor blockade in the ability of caffeine to promote MDMA "Ecstasy"-induced striatal dopamine release”. European Journal of Pharmacology. 650 (1): 220—8. PMID 20951694. doi:10.1016/j.ejphar.2010.10.012.
^ De Sarro G, Donato Di Paola E, Falconi U, Ferreri G, De Sarro A (1996). „Repeated treatment with adenosine A1 receptor agonist and antagonist modifies the anticonvulsant properties of CPPene”. European Journal of Pharmacology. 317 (2-3): 239—45. PMID 8997606. doi:10.1016/S0014-2999(96)00746-7.
^ Chwalczuk K, Rubaj A, Swiader M, Czuczwar SJ (2008). „[Influence of the antagonist of adenosine A1 receptors, 8-cyclopentyl-1 ,3-dipropylxanthine, upon the anticonvulsant activity of antiepileptic drugs in mice]”. Przegla̧d Lekarski (на језику: Polish). 65 (11): 759—63. PMID 19205356.

Vidi još уреди

CPX
Ksantin

Spoljašnje veze уреди

[1] Martinson EA, Johnson RA, Wells JN (1987). „Potent adenosine receptor antagonists that are selective for the A1 receptor subtype”. Molecular Pharmacology. 31 (3): 247—52. PMID 3561384. ^{[мртва веза]}

[2] Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA (1987). „8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors”. Naunyn-Schmiedeberg's Archives of Pharmacology. 336 (2): 204—10. PMID 2825043. doi:10.1007/BF00165806.

[pmid7680859-3] Ukena D, Schudt C, Sybrecht GW (1993). „Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes”. Biochemical Pharmacology. 45 (4): 847—51. PMID 7680859. doi:10.1016/0006-2952(93)90168-V.

[4] Coates J, Sheehan MJ, Strong P (1994). „1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?”. General Pharmacology. 25 (3): 387—94. PMID 7926579.

[5] Moro S, Gao ZG, Jacobson KA, Spalluto G (2006). „Progress in the pursuit of therapeutic adenosine receptor antagonists”. Medicinal Research Reviews. 26 (2): 131—59. PMID 16380972. doi:10.1002/med.20048.

[6] Vandam RJ, Shields EJ, Kelty JD (2008). „Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation”. BMC Neuroscience. 9: 95. PMC 2567986  . PMID 18826652. doi:10.1186/1471-2202-9-95.

[7] Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K (2008). „Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways”. Journal of Neuroscience Research. 86 (13): 2820—8. PMID 18618669. doi:10.1002/jnr.21742.

[8] Wu C, Wong T, Wu X, Sheppy E, Zhang L (2009). „Adenosine as an endogenous regulating factor of hippocampal sharp waves”. Hippocampus. 19 (2): 205—20. PMID 18785213. doi:10.1002/hipo.20497.

[9] Marek GJ (2009). „Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats”. Neuropharmacology. 56 (8): 1082—7. PMC 2706691  . PMID 19324062. doi:10.1016/j.neuropharm.2009.03.005.

[pmid20951694-10] Vanattou-Saïfoudine N, Gossen A, Harkin A (2011). „A role for adenosine A(1) receptor blockade in the ability of caffeine to promote MDMA "Ecstasy"-induced striatal dopamine release”. European Journal of Pharmacology. 650 (1): 220—8. PMID 20951694. doi:10.1016/j.ejphar.2010.10.012.

[pmid8997606-11] De Sarro G, Donato Di Paola E, Falconi U, Ferreri G, De Sarro A (1996). „Repeated treatment with adenosine A1 receptor agonist and antagonist modifies the anticonvulsant properties of CPPene”. European Journal of Pharmacology. 317 (2-3): 239—45. PMID 8997606. doi:10.1016/S0014-2999(96)00746-7.

[pmid19205356-12] Chwalczuk K, Rubaj A, Swiader M, Czuczwar SJ (2008). „[Influence of the antagonist of adenosine A1 receptors, 8-cyclopentyl-1 ,3-dipropylxanthine, upon the anticonvulsant activity of antiepileptic drugs in mice]”. Przegla̧d Lekarski (на језику: Polish). 65 (11): 759—63. PMID 19205356.

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