836-27-1Relevant academic research and scientific papers
5-Alkylresorcinol derivatives from the bryozoan Schizomavella mamillata: Isolation, synthesis, and antioxidant Activity
Ortega, María J.,Pantoja, Juan J.,De Los Reyes, Carolina,Zubía, Eva
, (2017)
The chemical study of the bryozoan Schizomavella mamillata has led to the isolation of six new 5-alkylresorcinol derivatives, schizols A–F (1–6), whose structures were established by spectrocospic means. Schizol A (1) exhibits a (E)-6-phenylnon-5-enyl moi
Identification of novel ROS inducers: Quinone derivatives tethered to long hydrocarbon chains
Hong, Yeonsun,Sengupta, Sandip,Hur, Wooyoung,Sim, Taebo
, p. 3739 - 3750 (2015/05/27)
We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 μM) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 μM) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.
Δ9-tetrahydrocannabinol immunochemical studies: Haptens, monoclonal antibodies, and a convenient synthesis of radiolabeled Δ9-tetrahydrocannabinol
Qi, Longwu,Yamamoto, Noboru,Meijler, Michael M.,Altobell III, Laurence J.,Koob, George F.,Wirsching, Peter,Janda, Kim D.
, p. 7389 - 7399 (2007/10/03)
Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Δ9- tetrahydrocannabinol (Δ9-THC); hence, monoclonal antibodies with high affinity and specificity for Δ9-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Δ9-THC and describe a convenient synthesis of radiolabeled Δ9-THC. We demonstrate the value and use of this probe to select anti-Δ9-THC antibodies that bind Δ9-THC with good affinity. The synthetic route to radiolabeled Δ9-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Δ9- THC and its analogues and the cannabinoid receptors.
Synthesis of 5',11-dihydroxy-Δ8-tetrahydrocannabinol
Huffman, John W.,Wu, Ming-Jung,Banner, W. Kenneth,Dai, Dong
, p. 13295 - 13306 (2007/10/03)
The synthesis of a polar cannabinoid, 5',11-dihydroxy-Δ8-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3,5-dimethoxyphenyl) pentane w
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
