- Metal ion-binding properties of 9-(4-phosphonobutyl)adenine (dPMEA), a sister compound of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), and quantification of the equilibria involving four Cu(PMEA) isomers
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The acidity constants of the threefold protonated acyclic 9-(4-phosphonobutyl)adenine, H3(dPMEA)+, as well as the stability constants of the M(H;dPMEA)+ and M(dPMEA) complexes with the metal ions M2+ = Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+ or Cd2+, have been determined by potentiometric pH titrations, in aqueous solution at I= 0.1 M (NaNO3) and 25 °C. Application of previously determined straight-line plots of log KM(R-PO3)M versus PKH(R-PO3)H for simple phosph(on)ate ligands, R-PO32-, where R represents a residue without an affinity for metal ions, proves that the primary binding site of dPMEA2- is the phosphonate group with all the metal ions studied; in fact, in most instances the stability is solely determined by the basicity of the phosphonate residue. Only for the Ni(dPMEA), Cu(dPMEA) and Cd(dPMEA) systems a stability increase due to macrochelate formation with the adenine residue occurs; the formation degrees are 21 ± 15%, 31 ± 14% and 29 ± 18%, respectively. In these three instances the additional interaction of the phosphonate-coordinated M2+ occurs most probably with N7; hence, dPMEA2- is more similar in its metal ion-binding properties to the parent nucleotide adenosine 5′-monophosphate (AMP2-) than to the antivirally active and structurally more related dianion of 9-[2-(phosphonomethoxy)ethyl]-adenine (PMEA2-). This result agrees with the observation that replacement of the ether O atom in PMEA by a CH2 unit leads to a compound, i.e. dPMEA, devoid of any biological activity. In addition, use is made of the stability enhancement obtained for the Cu(dPMEA) system due to macrochelate formation to analyze the equilibria regarding the four isomeric complex species possibly formed in the Cu(PMEA) system. It is shown that a macrochelated isomer involving N7 of the adenine residue occurs with Cu(PMEA) only in trace amounts; the important isomers in this system involve the ether oxygen (formation degree ca. 34%) and also N3 of the adenine moiety (ca. 41%). The Royal Society of Chemistry 2000.
- Gomez-Coca, Raquel B.,Kapinos, Larisa E.,Holy, Antonin,Vilaplana, Rosario A.,Gonzalez-Vilchez, Francisco,Sigel, Helmut
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Read Online
- The hydrophilizing agent for producing a self-emulsifiable polyisocyanate composition, a self-emulsifiable polyisocyanate compositions and coating composition (by machine translation)
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[A] a self-emulsifiable polyisocyanate composition has excellent adhesion to the substrate of a metal such as aluminum. (A) a compound represented by the formula [a] 1 anionic and, (b) organic polyisocyanate, and (c) a self-emulsifiable polyisocyanate com
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Paragraph 0095
(2020/12/30)
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- Synthesis and biological activity investigation of azole and quinone hybridized phosphonates
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Phosphonates, azoles and quinones are pharmacophores found in bioactive compounds. A series of phosphonates conjugated to azoles and quinones with variable carbon chain lengths were synthesized in 3–4 steps with good yield. Antifungal assay of these compounds showed that ethyl protected phosphates have excellent inhibitory activity against phytopathogenic fungus Fusarium graminearum, and the free-base phosphates have good activity against human pathogenic fungi Aspergillus flavus and Candida albicans. Structure- activity relationship (SAR) studies showed activity increases with longer carbon chain length between phosphonate and anthraquinone analogs consisting of azole and quinone moieties. These newly synthesized compounds also have mild antibacterial activities to Gram positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). Cytotoxicity analysis of these compounds against HeLa cells reveals that the phosphoric acid analogs are less toxic compared to ethyl protected phosphonates. Three leads compounds have been identified with prominent antifungal activity and low cytotoxicity.
- Subedi, Yagya Prasad,Alfindee, Madher N.,Shrestha, Jaya P.,Becker, Greg,Grilley, Michelle,Takemoto, Jon Y.,Chang, Cheng-Wei Tom
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supporting information
p. 3034 - 3037
(2018/08/09)
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- Synthesis of advanced fluorescent probes — water-soluble symmetrical tricarbocyanines with phosphonate groups
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A method for the synthesis of a series of water-soluble heptamethine indocyanine dyes containing a phosphonate group in the substituent bonded to the quaternary nitrogen atom of the indolenine moiety has been developed.
- Podrugina,Temnov,Doroshenko,Kuzmin,Nekipelova,Proskurnina,Zefirov
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p. 2722 - 2728
(2017/05/19)
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- The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs
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Inhibition of the nonmevalonate pathway (NMP) of isoprene biosynthesis has been examined as a source of new antibiotics with novel mechanisms of action. Dxr is the best studied of the NMP enzymes and several reports have described potent Dxr inhibitors. M
- Jackson, Emily R.,San Jose, Géraldine,Brothers, Robert C.,Edelstein, Emma K.,Sheldon, Zachary,Haymond, Amanda,Johny, Chinchu,Boshoff, Helena I.,Couch, Robin D.,Dowd, Cynthia S.
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p. 649 - 653
(2014/01/23)
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- Synthesis and characterization of aminophosphonates zirconium as new mesoporous materials
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A serial of aminophosphonates zirconium with the different arm lengths of -(CH2)n- organic chains (n=2-6) was synthesized for the first time. These compounds are characterized by FT-IR, SEM, TEM, TG and nitrogen adsorption-desorption. And based on the experimental data, these materials not only have layer structure mesoporous and good thermal stability such as zirconium phosphate, but also can be adjusted the layer distance, pore size and pore volume. So aminophosphonates zirconium posses special excellent properties and will have potential prospect applications.
- Zhou, Liang
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experimental part
p. 1320 - 1326
(2012/05/21)
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- ω-haloalkylphosphoryl compounds: Synthesis and properties
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A general method of the synthesis of ω-haloalkylphosphoryl compounds was developed, a series of compounds of phosphonic and phosphine oxide type were synthesized. The ability of some ω-haloalkylphosphonates to undergo intramolecular cyclization into the corresponding 1,2-oxaphospholane and 1,2-oxaphosphorine was investigated depending on the solvent polarity, the presence of halogen ions in the solution, and temperature. Tetrahydrofuran was chosen as one of the most suitable solvents for the alkylation of CH acids with ω-haloalkylphosphoryl compounds.
- Ragulin
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p. 1928 - 1937
(2013/06/05)
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- Synthesis of ω-phthalimidoalkylphosphonates
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A series of carbon chain growing ω-phthalimidoalkylphosphonates was prepared from simple and easy available raw materials by twostep reaction. The yields can reach 58 %-64 %. Their structures are confirmed by 1H NMR correctly.
- Zhou, Liang
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experimental part
p. 4821 - 4822
(2012/08/14)
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- Studies on the synthesis of a chiral salen Mn (III) complex immobilised onto zirconium aminophosphonates and catalytic asymmetric epoxidation of α-methylstyrene
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A chiral salen Mn (III) complex has been immobilised onto zirconium aminophosphonates by axial coordination with different linkage arm lengths (CH2)n (n = 2-6), to give a series of heterogeneous catalysts. The catalysts exhibited good to excellent catalytic efficiency in the asymmetric epoxidation of α-methylstyrene. One heterogeneous catalyst, with n = 6, gave higher catalytic properties than the original chiral salen Mn (III) complex in the NaClO/PPNO system. It can be easily recovered and reused several times without significant loss of activity.
- Zhou, Liang
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p. 512 - 515
(2012/10/29)
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- COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS
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The invention provides a novel class of compounds, immunogenic compositions and pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors 7. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine.
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Page/Page column 73
(2011/04/14)
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- Selective inhibition of Trypanosoma cruzi GAPDH by "bi-substrate" analogues
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A new series of "bi-substrate" analogues have been synthesized as potential inhibitors of the glyceraldehyde-3-phosphate dehydrogenase and one lead compound has been identified that inhibits the enzyme from Trypanosoma cruzi with good affinity and very high (50-fold) specificity. The Royal Society of Chemistry 2005.
- Ladame, Sylvain,Faure, Regis,Denier, Colette,Lakhdar-Ghazal, Faouzi,Willson, Michele
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p. 2070 - 2072
(2007/10/03)
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- Rapid and efficient Arbuzov reaction under microwave irradiation
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Diethyl alkylphosphonates are efficiently and rapidly prepared in good yields (75-99%) from trialkylphosphates and alkyl halides under short microwaves irradiations.
- Villemin, Didier,Simeon, Fabrice,Decreus, Hugues,Jaffres, Paul-Alain
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p. 209 - 213
(2007/10/03)
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- Enantioselective synthesis of both enantiomers of 2-amino-6-phosphonohexanoic acid [(R)- and (S)-AP6], a potent and specific agonist of AMPA receptor subtype
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The preparation of both enantiomers of 2-amino-6-phosphonohexanoic acid [(R)- and (S)-AP6] is described. The highly diastereoselective alkylation of imidazolidinones 4 and hydrolysis of the alkylated products [(2R,5R,1'S)-6 and (2S,5S,1'S)-6] proceeds under relatively mild conditions to give the physiologically important, enantiopure aminophosphonic acids (R)-AP6 and (S)-AP6.
- Garcia-Barradas, Oscar,Juaristi, Eusebio
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p. 1511 - 1514
(2007/10/03)
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- Intramolecular Catalysis of Dialkyl ω-Aminoalkylphosphonate Hydrolysis
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The influence that intramolecular catalysis of hydrolysis of O-alkyl S-alkylphosphonothioates by amino groups may have on the product distribution of the reaction is investigated by study of a series of model compounds.The hydrolysis of diethyl phosphonates and diethyl phosphonates has been investigated at 75 deg C over the pH range 8.21-11.45.Contributions to hydrolysis of the ethoxy groups by intramolecular catalysis by the amino groups have been identified for - and -phosphonates.Secondary and tertiary amino groups assist hydrolysis through general base catalysis.An additional contribution to hydrolysis of the secondary amino compounds by intramolecular nucleophilic catalysis is also observed.
- Leslie, D. Ralph,Pantelidis, Sue
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p. 545 - 560
(2007/10/02)
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- Synthesis of ω-phthalimidoalkylphosphonates
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Diethyl phthalimidoalkylphosphonates were synthesized by the reaction of diethyl bromoalkylphosphonates with N-(tert-butyldimethylsilyl)phthalimide in the presence of tetrabutylammonium fluoride.
- Chun,Park,Oh,Hong,Kim
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p. 909 - 910
(2007/10/02)
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- Syntheses de phosphobetaines amphiphiles neutres a distances intercharge variables
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Neutral amphiphilic phosphonato- and phosphinatobetaines having different interionic distances are synthesized.Two paths for this synthesis have been studied. 2-(Ethoxy or phenyl) 2-oxo 1,2-oxaphospholanes react with lipophilic tertiary amines at 150 deg C, giving rise to mixtures of phosphobetaines and oxaphospholanate ammonium salts.Lewis acids increase the reaction rate but cannot change the selectivity.The specific production of phosphobetaines is achieved by a three steps sequence: the Arbusov reaction is applied to α,ο-dibromoalcanes and triethylphosphite or phenyldiethylphosphonite, providing ο-bromophosphonates in high yield.Tertiary amines are then condensed, followed by a bromide to hydroxide ions exchange on an anion exchange resin.Phosphobetaines are then specifically formed by thermal elimination of ethanol above the critical micellar concentration.Howewer, when Hoffmann elimination competes with basic hydrolysis of the phenylphosphinic ester groups, acidic hydrolysis is preferred, followed by neutralization with an OH- anion exchange resin.This preparative specific synthesis procedure affords pure, neutral and inorganic salt free zwitterionic compounds for a whole series of homologues.The physical properties of such compounds are believed to be designed upon the chice of the substituents (alkyl chain length, interionic methylene number, ethoxy or phenyl substituent at the phosphorous atom).
- Germanaud, Laurent,Brunel, Sylvian,Chevalier, Yves,Le Perchec, Pierre
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p. 699 - 704
(2007/10/02)
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