- Formation of a tris(catecholato) iron(iii) complex with a nature-inspired cyclic peptoid ligand
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Siderophore-mimicking macrocyclic peptoids were synthesized. Peptoid3with intramolecular hydrogen bonds showed an optimally arranged primary coordination sphere leading to a stable catecholate-iron complex. The tris(catecholato) structure of 3-Fe(iii) was determined with UV-vis, fluorescence, and EPR spectroscopies and DFT calculations. The iron binding affinity was comparable to that of deferoxamine, with enhanced stability upon air exposure.
- Oh, Jinyoung,Kang, Dahyun,Hong, Sugyeong,Kim, Sun H.,Choi, Jun-Ho,Seo, Jiwon
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supporting information
p. 3459 - 3463
(2021/03/22)
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- Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines
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A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.
- Jong, Thingsoon,Bradley, Mark
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supporting information
p. 422 - 425
(2015/03/03)
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- An inorganic phosphate (Pi) sensor triggers 'turn-on' fluorescence response by removal of a Cu2+ ion from a Cu 2+-ligand sensor: Determination of Pi in biological samples
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A fluorescent ligand that displays a high selectivity for Cu2+ has been synthesized. On complexation with Cu2+, the fluorescence of the ligand is quenched. Inorganic phosphate ions decomplex Cu2+ displaying a fluorescence enhancement that can even be seen with naked eyes. The method was successfully used in quantitative determination of inorganic phosphates in serum, urine, and saliva samples.
- Hatai, Joydev,Pal, Suman,Bandyopadhyay, Subhajit
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supporting information; experimental part
p. 4357 - 4360
(2012/09/25)
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- An optimised synthesis of 2-[2,3-Bis(tert -butoxycarbonyl)guanidino] ethylamine
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This short report describes an improved, reliable, and high-yielding (>90%) synthesis of 2-[2,3-bis(tert-butoxycarbonyl)guanidino]ethylamine. The method is scalable (>5 g), and the product obtained directly from the reaction mixture requires no further purification. In addition, this methodology can be successfully applied to other diamine substrates (1,3-propyl and 1,4-butyl; 70% and 61% yield, respectively).
- Hickey, Shane M.,Ashton, Trent D.,Khosa, Simren K.,Pfeffer, Frederick M.
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scheme or table
p. 1779 - 1782
(2012/08/29)
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- Synthesis and photoluminescence study of di-dendron dendrimers derived from mono-Boc-protected ethylenediamine cores
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This work is focused on the synthesis and optical properties of cone-shaped structural feature di-dendron polyamidoamine dendrimers up to the third generation with mono-Boc-protected ethylenediamine (EDA) as a core. Strong UV absorbance spectra and fluorescence spectra from di-dendron dendrimers with different terminal groups (-NH2, -COOCH3) were studied under different conditions by varying experimental parameters such as concentration and pH. The optical density and fluorescence intensities increased when di-dendron dendrimers generation number increased from 0.5 to 3.0. It was confirmed that the concentration of di-dendron dendrimers plays an important role in fluorescence intensity. The increase in fluorescence intensity was linear in low concentration regions, but the intensity increased slowly in high concentration regions. The results also showed a rapid increase in fluorescence intensity at low pH. The formation of a fluorescence-emitting moiety had a close relationship to protonated tertiary amine groups in di-dendron dendrimers derived from mono-Boc-protected EDA cores. Furthermore, the formation of fluorescent chemical species was irreversible. Copyright
- Zhao, Yili,Liu, Sen,Jiang, Wei,Chang, Yulei,Li, Yapeng,Fang, Xuexun,Wang, Jingyuan
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experimental part
p. 264 - 270
(2012/07/13)
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- A fluorescent polymeric heparin sensor
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Linear copolymers have been developed which carry binding sites tailored for sulfated sugars. All binding monomers are based on the methacrylamide skeleton and ensure statistical radical copolymerization. They are decorated with o-aminomethylphenylboronates for covalent ester formation and/ or alkylammonium ions for noncovalent Coulomb attraction. Alcohol sidechains maintain a high water solubility; a dansyl monomer was constructed as a fluorescence label. Statistical copoly merization of comonomer mixtures with optimized ratios was started by AIBN (AIBN = 2,2′-azoisobutyronitrile) and furnished water-soluble comonomers with an exceptionally high affinity for glucosaminoglucans. Heparin can be quantitatively detected with an unprecedented 30 nM sensitivity, and a neutral polymer without any ammonium cation is still able to bind the target with almost micromolar affinity. From this unexpected result, we propose a new binding scheme between the boronate and a sulfated ethylene glycol or aminoethanol unit. Although the mechanism of heparin binding involves covalent boronate ester formation, it can be completely reversed by protamine addition, similar to heparin's complex formation with antithrombin III.
- Sun, Wei,Bandmann, Heinz,Schrader, Thomas
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p. 7701 - 7707
(2008/03/14)
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- Synthesis of ATRP-induced dextran-b-polystyrene diblock copolymers and preliminary investigation of their self-assembly in water
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Dextran-b-polystyrene diblock copolymers forming miscellaneous spherical self-assemblies in water were obtained by chemical modification of the anomeric extremity of a commercial dextran followed by atom transfer radical polymerisation of styrene. The Royal Society of Chemistry.
- Houga, Clement,Meins, Jean-Francois Le,Borsali, Redouane,Taton, Daniel,Gnanou, Yves
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p. 3063 - 3065
(2008/03/14)
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- Metal-assisted assembly and stabilization of collagen-like triple helices
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Single-chain and TRIS-assembled collagen mimetic peptide structures incorporating catechol groups were synthesized. When 1/3 equiv of Fe3+ was added to the single-chain compound in 50 mM CAPS buffer (pH 10), the 1:3 Fe3+-catechol complex that formed acted as an N-terminal scaffold to assemble the triple helix. When 1 equiv of Fe3+ was added to the TRIS-assembled compound in the buffer solution, the Fe3+-catechol complex acted as an extra C-terminal scaffold, which lead to a triple helix with both termini tethered. The formation of this C-terminal complex increased the Tm by a remarkable 22 °C! Copyright
- Cai, Weibo,Kwok, Sen Wai,Taulane, Joseph P.,Goodman, Murray
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p. 15030 - 15031
(2007/10/03)
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- Fluorobenzamides and uses thereof
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The invention relates to fluorobenzamide derivatives of the formula wherein R1, R2, R3 R4, R5, R6 and R7 are as defined herein. =, The compounds of the invention are selective monoamine oxidase B inhibitors and therefore they are suitable for the treatment of diseases mediated by monoamine oxidase B, such as Alzheimer's disease or senile dementia.
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- Solid-phase synthesis of oligourea peptidomimetics
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A procedure for the solid-phase synthesis of oligourea peptidomimetics starting from Boc-protected monomers is described. The compounds are prepared on Tentagel resin and can be obtained selectively rather as the C-terminal free acids with UV irradiation
- Boeijen, Astrid,Liskamp, Rob M. J.
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p. 2127 - 2135
(2007/10/03)
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- COMPOUNDS FOR TREATING AND PREVENTING COGNITIVE DISEASES AND DEPRESSION AND METHODS OF MAKING SAME
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Ethylenediamine monoamides of the formula R--CO--NH--CH2 --CH2 --NH2. wherein R is one of groups in which R1 is phenyl monohalophenyl, monolower-alkylphenyl, monolower-alkoxypheynl, monotrifluoromethylphenyl, monocyanophenyl or monoaryl-lower-alkoxyphenyl, dihalophenyl, furyl, thienyl or monohalothienyl, R2 is hydrogen, halogen or amino, R3, R5 and R7 each are phenyl, monohalophenyl, dihalophenyl, thienyl, furyl or monohalofuryl, R4 and R6 each are hydrogen or amino and R8 is hydrogen or lower-alkyl, as well as their pharmaceutically usable acid addition salts are disclosed. The compounds have monoamine oxidase inhibiting properties with low toxicity and are useful for the treatment of depressive states and cognitive disorders
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- Search for the pharamcophore of the K+ channel blocker, apamin
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The suggestion that the arginine residues, 13Arg and 14Arg, in the octadecapeptide apamin 1 are critically important to its action in blocking Ca2+-dependent K+ channels (and hence part of the 'pharmacophore') has been investigated by examining small peptides containing Arg-Arg or Lys-Arg. Bisguanidine derivatives modelled on the Arg-Arg partial pharmacophore have also been synthesised and tested; in particular, N-(2-guanidinoethyl)-3[N1-(2-guanidinoethyl)carbamoyl]-trans-propena mide 11 and its higher homologue 12. None of the compounds showed more than weak activity (K(i) > 10-5 M) indicating that although the Arg-Arg fragment may be necessary, it is not a sufficient atom grouping for the pharmacophore.
- Demonchaux,Granellin,Dunn,Haylett,Jenkinson
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p. 915 - 920
(2007/10/02)
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- Mono-protected Diamines. N-tert-Butoxycarbonyl-α,ω-alkanediamines from α,ω-Alkanediamines
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We wish to report a convenient pathway to N-tert-butoxycarbonyl-α,ω-alanediamines 2a-e by treatment of the corresponding α,ω-alkanediamine with di-tert-butyl dicarbonate in dioxane as the solvent.Only small amounts of the bis-substituted N,N'-tert-butoxycarbonyl-α,ω-aldnediamines 3a-e were formed (2-9percent) which were easily removed by an aquous workup.The α,ω-alkane-aza-diamine 4 was also mono-protected (62percent yield of 5) by the same methodology.
- Krapcho, A. Paul,Kuell, Christopher S.
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p. 2559 - 2564
(2007/10/02)
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- Synthesis of diethylenetriaminepentaacetic acid conjugated inulin and utility for cellular uptake of liposomes
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The synthesis, binding of radioactivity cations, liposomal encapsulation, and biodistribution of the oxidized-insulin reaction product with ethylenediamine and diethylenetriaminepentaacetic acid (4) are described. The four-step synthesis of the inulin derivative proceeded in a good overall yield of 72%. The complex of the inu7lin derivative with either 67Ga3+ or 111In3+ was stable in vivo and di not readily distribute into tissues, being excreted primarily in urine after intravenous administration to mice. The liposome-entrapped inulin derivative can be loaded with radioactive heavy metal cations by mobile ionophores in high radiochemical yields of 80-91%. Following the intravenous administration of the liposomal encapsulation of the indium-111-labeled inulin derivative, the entrapped compound had a biodistribution characteristic of liposomes and allowed an estimation of the extent of the intracellular uptake of liposomes. The ability of the inulin derivative to chelate many different types of metals will allow the use of this probe for studying subtle differences in tissue distribution resulting from different drug targeting or delivery protocols in the same animal by multiple labeling techniques. Moreover, the chelate-conjugated inulin permits studies of the applications of drug delivery systems in primates or human subjects by noninvasive techniques such as γ-scintigraphic or nuclear magnetic resonance imaging methods.
- Essien,Lai,Hwang
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p. 898 - 901
(2007/10/02)
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