1102-88-1Relevant articles and documents
A Mild Oxidizing Reagent for Alcohols and 1,2-Diols: o-Iodoxybenzoic Acid (IBX) in DMSO
Frigerio, Marco,Santagostino, Marco
, p. 8019 - 8022 (1994)
o-Iodoxybenzoic acid (IBX) smoothly oxidizes primary and secondary alcohols to aldehydes and ketones, respectively. 1,2-Diols are converted to α-ketols or α-diketones without any oxidative cleavage of the glycol C-C bond.IBX oxidations are easily conducted in DMSO solution at room temperature, with yields ranging from good to quantitative.
BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF DIGITALIS PURPUREA
Hirotani, Masao,Furuya, Tsutomu
, p. 531 - 534 (1980)
Digitoxigenin was oxidized to digitoxigenone which was reduced to epidigitoxigenin and then glucosylated to epidigitoxigenin glucoside by cell cultures of Digitalis purpurea.The epidigitoxigenin glucoside, together with digitoxigenone and epidigitoxigenin, was isolated in considerable amounts, whereas digitoxigenin glucoside could only be detected in low concentration.Furthermore, it was confirmed by TLC and HPLC that digitoxigenin was hydroxylated to periplogenin.Key Word Index-Digitalis purpurea; Scrophulariaceae; tissue cultures; biotransformation; hydroxylation; glucosylation; steroid; digitoxigenin; digitoxigenone; epidigitoxigenin; periplogenin; digitoxigenin glucoside; epidigitoxigenin glucoside.
BIOTRANSFORMATION OF DIGITOXIGENIN BY CELL SUSPENSION CULTURES OF STROPHANTHUS INTERMEDIUS
Kawaguchi, Kiichiro,Hirotani, Masao,Furuya, Tsutomu
, p. 1093 - 1098 (1989)
Biotransformation products of digitoxigenin by cell suspension cultures of Strophanthus intermedius were isolated and their structures elucidated as 3-epidigitoxigenin, 3-epi-17βH-digitoxigenin, gitoxigenin, periplogenin, 3-epigitoxigenin, 3-epiperiplogenin and digitoxigenin β-D-glucoside, respectively.Furthermore, 3-epi-17βH-periplogenin, 3-epidigitoxigenin β-D-glucoside and digitoxigenone were identified by TLC and HPLC.Biotransformation reactions of the digitoxigenin molecule by plant cell cultures are summarized and discussed comparatively. - Keywords: Strophanthus intermedius; Apocynaceae; cell cultures; biotransformation; 5β- and 16β-hydroxylation; cardenolides; digitoxigenin; 3-epigitoxigenin.
Efficient synthesis of 3-aminodigoxigenin and 3-aminodigitoxigenin probes
Adamczyk, Maciej,Grote, Jonathan
, p. 771 - 774 (1999)
Oxidation of digoxigenin and digitoxigenin to the 3-ketones followed by reductive amination produced a mixture of amine epimers. The inability to separate the epimeric mixtures of chemiluminescent digoxigenin probes derived by conjugation to the acridinium label prompted us to develop an HPLC method to separate the amines. Labeling of the pure amines resulted in good yields of the isomerically pure probes.
Potential anti-herpes and cytotoxic action of novel semisynthetic digitoxigenin-derivatives
Boff, Laurita,Munkert, Jennifer,Ottoni, Flaviano Melo,Zanchett Schneider, Naira Fernanda,Ramos, Gabriela Silva,Kreis, Wolfgang,Fernandes de Andrade, Saulo,Dias de Souza Filho, José,Braga, Fern?o Castro,Alves, Ricardo José,Maia de Pádua, Rodrigo,Oliveira Sim?es, Cláudia Maria
, p. 546 - 561 (2019/02/25)
In recent years, new therapeutic possibilities were proposed for cardiac glycosides traditionally used to treat heart diseases, such as anticancer and antiviral activities. In this sense, this work aimed to synthesize the readily accessible 3β-azido-3-deoxydigitoxigenin (5) from digitoxigenin (1). Two new series of compounds were obtained from derivative (5): (i) O-glycosyl trizols through click chemistry with propargyl glycosides; and (ii) compounds substituted in the alpha carbonyl position with different residues linked via an amino-group. All obtained derivatives have their chemical structures confirmed, and their anti-herpes (against HSV-types 1 and 2 replication) and cytotoxic (against PC3, A549, HCT-8 and LNCaP cell lines) activities evaluated. Compounds 10 and 11 exhibited the most promising results against HSV-1 (KOS and 29-R strains) and HSV-2 (333 strain) replication with SI values > 1000. Both compounds were also the most cytotoxic for the human cancer cell lines tested with IC50 values similar to those of paclitaxel. They also presented reduced toxicity toward non-cancerous cell lines (MRC-5 and HGF cells). Promising compounds were tested in regard to their ability to inhibit Na+/K+-ATPase. The inhibition rate correlates suitably with the bioactivity demonstrated by those both compounds against the different human cancer cells tested as well as against HSV replication. Moreover, the results showed that specific chemical features of compound 10 and 11 influenced the bioactivities tested. In summary, it was possible to obtain novel digitoxigenin-derivatives with remarkable cytotoxic and anti-herpes activities as well as low toxicity and high selectivity. In this way, they could be considered potential molecules for the development of new drugs.
Synthesis and evaluation of cardiac glycoside mimics as potential anticancer drugs
Jensen, Marie,Schmidt, Steffen,Fedosova, Natalya U.,Mollenhauer, Jan,Jensen, Henrik H.
experimental part, p. 2407 - 2417 (2011/05/12)
The cardiac glycoside digitoxin, consisting of a steroid core linked to a labile trisaccharide, has been used for centuries for the treatment of congestive heart failure. The well known pharmacological effect is a result of the ability of cardiac glycosides to inhibit the Na+, K +-ATPase. Within recent years cardiac glycosides have furthermore been suggested to possess valuable anticancer activity. To mimic the labile trisaccharide of digitoxin with a stabile carbohydrate surrogate, we have used sulfur linked ethylene glycol moieties of varying length (mono-, di-, tri- or tetra-ethylene glycol), and furthermore used these linkers as handles for the synthesis of bivalent steroids. The prepared compounds were evaluated for their potencies to inhibit the Na+, K+-ATPase and for their cytotoxic effect on cancerous MCF-7 cells. A clear trend is observed in both inhibition and cytotoxic effect, where the bioactivity decreases as the size increases. The most potent Na+, K+-ATPase inhibitors are the compounds with the shortest ethylene glycol chain (Kapp 0.48 μM) and thiodigitoxigenin (Kapp 0.42 μM), which both are comparable with digitoxigenin (Kapp 0.52 μM). For the cancer cell viability assay the shortest mimics were found to have highest efficacy, with the best ligand having a monoethylene glycol unit (IC50 0.24 μM), which was slightly better than digitoxigenin (IC50 0.64 μM), while none of the novel cardiac glycoside mimics display an in vitro effect as high as digitoxin (IC50 0.02 μM).
Modifying the glycosidic linkage in digitoxin analogs provides selective cytotoxins
Langenhan, Joseph M.,Engle, Jeffery M.,Slevin, Lauren K.,Fay, Lindsay R.,Lucker, Ryan W.,Smith, Kyle R.,Endo, Matthew M.
, p. 670 - 673 (2008/09/19)
A chemoselective reaction between oxyamines and unprotected, unactivated reducing sugars was used to construct for the first time a panel of linkage-diversified neoglycosides. This panel of digitoxin analogs included potent and selective tumor cytotoxins; cytotoxicity was dependent on the structure of the glycosidic linkage. These results validate linkage diversification through neoglycosylation as a unique and simple strategy to powerfully complement existing methods for the optimization of glycoconjugates.
