C101

8-Cyclopentyl-1,3-dipropylxanthine

A1 adenosine receptor antagonist, solid

• Sinónimos: 1,3-Dipropyl-8-cyclopentylxanthine, DPCPX, PD 116,948
• Fórmula empírica (notación de Hill): C₁₆H₂₄N₄O₂
• Número CAS: 102146-07-6
• Peso molecular: 304.39
• UNSPSC Code: 12352202
• PubChem Substance ID: 24277697
• NACRES: NA.77
• MDL number: MFCD00055117
• Form: solid

Propiedades

• Nombre del producto: 8-Cyclopentyl-1,3-dipropylxanthine, solid
• form: solid
• Quality Segment: 100
• color: white
• solubility: DMSO: >10 mg/mL, 0.1 M NaOH: 2 mg/mL, ethanol: 4 mg/mL, H₂O: insoluble
• εmax: 14,800 at 276 nm in ethanol
• SMILES string: CCCN1C(=O)N(CCC)c2nc([nH]c2C1=O)C3CCCC3
• 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)
• InChI key: FFBDFADSZUINTG-UHFFFAOYSA-N
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) ; rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Adora3(25370)

Descripción

Application

8-Cyclopentyl-1,3-dipropylxanthine has been used as an adenosine receptor (A1AR) antagonist in macrophages[1] and human umbilical vein endothelial cells (HUVECs).[2] It has also been used as A1AR antagonist in MCF-7 breast cancer cell line to test its anti-cancer effect.[3]

Biochem/physiol Actions

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective A1 adenosine receptor antagonist.[4] DPCPX possesses anti-cancer functionality. It induces apoptosis in breast cancer cells and favors mRNA expression of caspases.[3]

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Información de seguridad

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Clase de almacenamiento: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves