95215-72-8Relevant academic research and scientific papers
A practical route for the preparation of 1,4,7-triazacyclononanyl diacetates with a hydroxypyridinonate pendant arm
Gai, Yongkang,Hu, Zhongping,Rong, Zhao,Ma, Xiang,Xiang, Guangya
, p. 19393 - 19405 (2015)
The preparation of triazamacrocyclic hydroxypyridinonate (HOPO-TACN) derivatives as potential chelators for metals in biomedical applications was reported. The synthesis is based on a convergent synthetic approach, in which the key intermediate di-tert-butyl-2,2′-(1,4,7-triazonane-1,4-diyl) diacetate was coupled with a hydroxypyridinonate pendant arm. The method is suitable for rapid syntheses of metal chelator HOPO-TACNs of biomedical interest.
3,2-Hydroxypyridinone-Grafted Chitosan Oligosaccharide Nanoparticles as Efficient Decorporation Agents for Simultaneous Removal of Uranium and Radiation-Induced Reactive Oxygen Species in Vivo
Shi, Cen,Wang, Xiaomei,Wan, Jianmei,Zhang, Duo,Yi, Xuan,Bai, Zhuanling,Yang, Kai,Diwu, Juan,Chai, Zhifang,Wang, Shuao
, p. 3896 - 3905 (2018)
Most of the key radionuclides in the nuclear fuel cycle, such as actinides, possess a combination of heavy metal chemotoxicity and radiotoxicity and therefore represent a severe threat to the ecological environment and public safety. The radiotoxicity originates from direct radiation-induced organ damage and indirect damage, mostly through radiation-induced reactive oxygen species (ROS). Although effective chelating agents that can accelerate the excretion of actinides, such as uranium, have been developed in the past several decades, very few of them can reduce radiation-induced damage from internal contamination. In fact, the strategy of simultaneous removal of actinides and their induced-ROS in vivo has scarcely been considered. Here, we report a 3,2-hydroxypyridinone-grafted chitosan oligosaccharide nanoparticle (COS-HOPO) as a new type of decorporation agent that is effective for the removal of both uranium and ROS in vivo. The cytotoxicity and decorporation assays indicate that the marriage of chitosan oligosaccharide (COS) and hydroxypyridinone (HOPO) gives rise to a remarkable decrease in toxicity and promotion of the uranium removal capability from both kidneys and femurs. The decorporation efficacy can reach up to 43% in rat proximal tubular epithelial cells (NRK-52E), 44% in kidneys, and 32% in femurs. Moreover, the ROS levels of the cells treated with COS-HOPO are significantly lower than those of the control group, implying a promising radiation protection effect. The detoxification mechanism of COS-HOPO is closely related to both chelating U(VI)- and scavenging U(VI)-induced intracellular ROS.
Hydroxypyridinone type depleted-uranium discharge promoting agent and its preparation method and application
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, (2017/08/28)
The invention discloses a hydroxypyridinone type depleted-uranium discharge promoting agent and its preparation method and application. The hydroxypyridinone type depleted-uranium discharge promoting agent is characterized in that ethyl bromoacetate and 2
Hydroxy-pyridone ligand and application thereof
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Paragraph 0051; 0055; 0056, (2017/08/30)
The invention relates to a hydroxy-pyridone ligand; a structural formula of the hydroxy-pyridone ligand is one of two formulas described in the description, wherein a structural formula of R is described in the description, R1 is hydrogen, alkyl of C2-C4, halogen, hydroxyl or carboxyl, m, n and p are independently selected from 1, 2 or 3, and r is 1 or 2. A preparation method of the hydroxy-pyridone ligand comprises the following steps: dissolving a compound as shown in a formula (1) into an organic solvent, and then enabling the obtained solution to react with an amino-terminated compound at the temperature of 25-35 DEG C in presence of a catalyst to obtain an intermediate compound; enabling the obtained intermediate compound to have a palladium-carbon reduction reaction in an organic solvent to obtain the hydroxy-pyridone ligand, wherein a structural formula of the compound as shown in the formula (1) is described in the description, and R1 is hydrogen, alkyl of C2-C4, halogen, hydroxyl, carboxyl or aryl. The invention also provides application of the hydroxy-pyridone ligand as chelating agents for lanthanide elements, actinide elements and/or heavy metal elements. The invention further provides application of the hydroxy-pyridone ligand as a chelating agent for the element in nuclear waste, wherein the element in the nuclear waste is Sr, Cs, Tc or I.
Organometallic ruthenium and osmium compounds of pyridin-2- and -4-ones as potential anticancer agents
Henke, Helena,Kandioller, Wolfgang,Keppler, Bernhard K.,Hartinger, Christian G.,Hanif, Muhammad
, p. 1718 - 1727,10 (2020/08/24)
Organometallic RuII compounds are among the most widely studied anticancer agents. Functionalizing metal centers with biomolecule-derived ligands has been shown to be a promising strategy to improve the antiproliferative activity of metal-based chemotherapeutics. Herein, the synthesis of a series of novel 3-hydroxypyridin-2-one-derived ligands and their MII(η6-p-cymene) half-sandwich complexes (M=Ru, Os) is described. The compounds were characterized by 1D- and 2D-NMR spectroscopy, and elemental analysis. Copyright
New ligand bearing preorganized binding side-arms interacting with ammonium cations: Synthesis, conformational studies and crystal structure
Formica, Mauro,Fusi, Vieri,Giorgi, Luca,Guerri, Annalisa,Lucarini, Simone,Micheloni, Mauro,Paoli, Paola,Pontellini, Roberto,Rossi, Patrizia,Tarzia, Giorgio,Zappia, Giovanni
, p. 1575 - 1583 (2007/10/03)
The synthesis and characterization of the new tetraazamacrocycle 4-(N),10-(N)-bis[2-(3-hydroxy-2-oxo-2H-pyridin-1-yl)acetamido]-1,7-dimethyl-1,4, 7,10-tetraazacyclododecane (L) is reported. L shows two 3-(hydroxy)-1- (carbonylmethylen)-2(1H)-pyridinone moieties as side-arms of a tetra-aza-macrocyclic base. The key coupling of side-arms was studied and the most significant results were obtained by activating the 3-(benzyloxy)-1- (carboxymethyl)-2(1H)-pyridinone as pentafluorophenol ester. The acid-base properties of L and its capability to interact with simple ammonium cations were investigated by potentiometric measurements in aqueous solution (298.1 ± 0.1 K, I = 0.15 mol dm-3). Protonated species of L can bind NH4+ or primary ammonium cations such as MeNH 3+ discriminating them from secondary or tertiary ammonium cations such as Me2NH2+ or Me 3NH+ which are not bound in aqueous solution. 1H and 13C NMR spectra showed the existence in solution of two conformers on the NMR time scale due to the rotational restriction of the two N-C=O groups. The activation parameters were determined by dynamic variable-temperature NMR analysis. Molecular dynamics calculations gave results in agreement with the experimental data for both conformation and ammonium-binding studies, underlining that the transformation of the two secondary amines of the macrocyclic base to amide functions, forces the side-arms to remain fixed in position, almost face to face and thus to be preorganized to interact with other species. The crystal structure of the [HL]Cl·8H2O species shows the high number of preorganized hydrogen bond sites capable, in this case, of interacting directly with five H2O molecules.
Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties, and biological activity
Streater,Taylor,Hider,Porter
, p. 1749 - 1755 (2007/10/02)
The synthesis of a range of novel bidentate and hexadentate ligands containing the chelating moiety 3-hydroxy-2(1H)-pyridinone is described. The pK(a) values of the ligands and the stability constants of their iron(III) complexes have been determined. The stability constant of the iron(III) complex of one of the hexadentate ligands is comparable to that of desferrioxamine B. The distribution coefficients of the ligands and their iron(III) complexes were also determined. One of the novel hexadentate compounds has been shown to markedly enhance iron(III) excretion from both hepatocytes and iron-overloaded mice.
Iron-pyridone complexes for anemia
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, (2008/06/13)
Pharmaceutical compositions containing an iron complex of a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionizable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by aliphatic hydrocarbon groups, are of value for the treatment of iron deficiency anemia.
Pharmaceutical compositions of hydroxypyridones
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, (2008/06/13)
Compounds in which two or more rings, being a 3-hydroxypypyrid-2-one, 3-hydroxypyrid-4-one or 1-hydroxpyrid-2-one, are linked are of value in the treatment of patients having a toxic concentration of a metal, particularly iron, in the body while the iron complexes of such compounds are of value in the treatment of iron deficiency anaemia.
Pharmaceutical compositions
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, (2008/06/13)
Pharmaceutical compositions containing a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionizable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group, but excluding compounds in which said replacement of hydrogen atoms in the compound is effected only by aliphatic hydrocarbon groups, or a salt thereof containing a physiologically acceptable ion or ions, are of value for removing toxic amounts of metals, particularly iron, from the body.
