CHEMBL1451750 8-(Benzylamino)Caffeine BDBM50259318
8-(3-Bromobenzyloxy)caffeine BDBM50306698 CHEMBL602464
BDBM50306701 8-(3-Methylbenzyloxy)caffeine CHEMBL589765
CHEMBL602260 8-(3-Chlorobenzyloxy)caffeine BDBM50306697
CHEMBL602465 BDBM50306699 8-(3-Fluorobenzyloxy)caffeine
CHEMBL602880 BDBM50306702 8-(3-Methoxybenzyloxy)caffeine
8-[(3-Trifluoromethyl)benzyloxy]caffeine BDBM50306700 CHEMBL602466
BDBM110136 (E)-8-(3,4-Dichlorostyryl)caffeine (4b)
BDBM50264556 CHEMBL483243 (Z)-8-(3-chlorostyryl)caffeine
CHEMBL2313284 BDBM50425477 (E)-8-(4-Chlorostyryl)caffeine (4a)
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione caffeine Caffeine (1,3,7-trimethylxanthine) 1,3,7-trimethyl-3,7-dihydropurine-2,6-dione CHEMBL113 BDBM10849
BDBM50264585 CHEMBL483663 (E,E)-8-(4-Phenylbutadien-1-yl)caffeine
BDBM50264622 CHEMBL489390 (E,E)-8-[4-(3-Chlorophenyl)butadien-1-yl]caffeine
BDBM50264623 (E,E)-8-[4-(3-Fluorophenyl)butadien-1-yl]caffeine CHEMBL489391
CHEMBL522256 (E,E)-8-[4-(3-Bromophenyl)butadien-1-yl]caffeine BDBM50264624
CSC 8-[(E)-2-(3-chlorophenyl)ethenyl]-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione BDBM50037429 8-(3-chlorostyryl)caffeine cid_5353365 CHEMBL26138
8-(3-chlorostyryl)caffeine (CSC) BDBM11018 2-[(E)-2-(3-chlorophenyl)ethenyl]-3,5,7-trimethyl-3H,4H,5H,6H,7H-imidazo[4,5-c]pyridine-4,6-dione
- Mostert, S; Mentz, W; Petzer, A; Bergh, JJ; Petzer, JP Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues. Bioorg Med Chem 20: 7040-50 (2012)
- Daly, JW; Padgett, WL; Shamim, MT Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors. J Med Chem 29: 1305-8 (1987)
- Sethi, KK; Sahoo, SK; Pichikala, JN; Suresh, P Carbonic anhydrase I and II inhibition with natural products: caffeine and piperine. J Enzyme Inhib Med Chem 27: 97-100 (2012)
- Ishiyama, H; Nakajima, H; Nakata, H; Kobayashi, J Synthesis of hybrid analogues of caffeine and eudistomin D and its affinity for adenosine receptors. Bioorg Med Chem 17: 4280-4 (2009)
- Ohshita, K; Ishiyama, H; Oyanagi, K; Nakata, H; Kobayashi, J Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors. Bioorg Med Chem 15: 3235-40 (2007)
- Rivara, S; Piersanti, G; Bartoccini, F; Diamantini, G; Pala, D; Riccioni, T; Stasi, MA; Cabri, W; Borsini, F; Mor, M; Tarzia, G; Minetti, P Synthesis of (E)-8-(3-chlorostyryl)caffeine analogues leading to 9-deazaxanthine derivatives as dual A(2A) antagonists/MAO-B inhibitors. J Med Chem 56: 1247-61 (2013)
- Pretorius, J; Malan, SF; Castagnoli, N; Bergh, JJ; Petzer, JP Dual inhibition of monoamine oxidase B and antagonism of the adenosine A(2A) receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues. Bioorg Med Chem 16: 8676-84 (2008)
- ChEMBL_1772937 Inhibition of human supersome CYP1A2 using caffeine as substrate assessed as caffeine 3-N-demethylation after 30 mins by HPLC-UV detection
- ChEMBL_52551 Inhibition of human cytochrome P450 1A2 activity as caffeine N3 demethylation (500 uM)
- ChEMBL_1923414 Inhibition of human CYP1A2 expressed in supersomes assessed as caffeine 3-N-demethylation after 15 mins by HPLC analysis
- Glycogen Phosphorylase Activity Assay The activity of recombinant human liver GPa in the forward direction was measured by monitoring the production of NADPH. Enzyme activity was assayed at pH 6.8 in phosphate buffer containing beta-NADP, alpha -glucose 1,6-bisphosphate, glucose-6-phophate dehydrogenase, phosphoglucomutase, glycogen, and glucose. The basal rate of hLGPa enzyme activity in the absence of inhibitors (Control) was determined by adding DMSO alone, and a fully-inhibited rate of hLGPa enzyme activity was obtained by adding the positive control test substance, 200 mM caffeine. The reaction was started by adding hLGPa solution (beta-glycerophosphate and cystein, pH 6.8). The reaction took place at room temperature, and the conversion of oxidized beta-NADP to reduced beta-NADPH was measured at 340 nm for 2 h. The hLGPa inhibition IC50 values were calculated using the logistic regression method and SAS software.
- GPa Inhibition Assay RMGPa (Rabbit Muscle Glycogen Phosphorylase a) activity was measured in the direction of glycogen synthesis by the formation of inorganic phosphate from glucose-1-phosphate using a 384 well plate at 22 deg with a 30 min incubation time. Phosphate was measured at 620 nm, 5 min after the addition of ammonium molybdate and malachite green. Test compounds were added to the assay. Compounds were tested against a caffeine standard in 11 point concentration-response curve in duplicate on two separate occasions. Data was analyzed using GraphPad Prism v.4.03.A nonlinear regression (curve fit) analysis with a sigmoidal dose-response equation (variable slope) was applied to generate IC50 and Hill slope values. The reported IC50 had a Hill slope between 0.7 and 1.2 and a Z value of ~0.8. Compounds were screened with maximal concentrations of 222 uM. The assay was carefully monitored for signs of compound insolubility. The results are presented as mean values from 4 determinations. Samples used in screening were of 98-100% purity.