Iminodiacetic acids based on vinylamine-vinylpyrrolidone copolymers

Tikhonova, L.I.; Samoilova, O. I.; Panarin, Ye.F.; Yashunskii, V. G.

doi:10.1016/0032-3950(74)90300-1

Cited by 4 publications

(6 citation statements)

References 7 publications

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“…Synthesis of copolymers containing N-vinyliminodiacetic acid units was carried out according to Scheme 1. First, radical copolymerization of N-vinylformamide with N-vinylpyrrolidone was carried out according to the procedure described in [28]; then the product was hydrolyzed, and partial alkylation of amino groups with sodium monochloroacetate was performed.…”

Section: Resultsmentioning

confidence: 99%

“…The results are given in Table 1. In calculations of weight-average (M w ) and number-average (M n ) molecular masses and polydispersity index M w /M n , we used the Mark-Kuhn-Houwink (MKH) constants for poly(N-vinylpyrrolidone) and poly(N-vinylformamide) [28]. UV spectrum of the synthesized model complex Ga(IDA) 2 Na has the single characteristic absorption maximum in the area of 210-230 nm that is attributed to charge transfer from metal to ligand.…”

Section: Resultsmentioning

confidence: 99%

“…The starting monomers (VP and VFA, Aldrich) were purified by vacuum distillation at 10−2 ppm. Polymerization was carried out in closed vials in argon atmosphere according to the procedure described in [28] (Scheme A, D). Azobisisobutyronitrile (AIBN, 1-2 wt.% with respect to amounts ofloaded monomers) was used as an initiator; the reaction proceeded in ethanol or isopropanol at 60 • C in inert atmosphere for 24 hours.…”

Section: Synthesis Of Vp-vfa and Vp-vacopolymersmentioning

confidence: 99%

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Metal-Polymer Complexes of Gallium/Gallium-68 with Copolymers of N-Vinylpyrrolidonewith N-Vinylformamideand N-Vinyliminodiacetic Acid: A Hint for Radiolabeling of Water-Soluble Synthetic Flexible Chain Macromolecules

et al. 2020

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Copolymer of N-vinylpyrrolidone (VP) with vinylformamide (VFA) and N-vinyliminodiacetic acid (VIDA) was synthesized; its metal-polymer complexes (MPCs) with gallium were obtained. The complexes were characterized by size exclusion chromatography, hydrodynamic and optical methods, scanning electron microscopy, and spectral methods (UV, IR, 1Н NMR spectroscopy). It was demonstrated that in going from polymer to complex, hydrodynamic parameters of macromolecules change only slightly, although the polymer contains intramolecular Ga(VIDA)2 fragments in its structure. A new method for preparation of MPCs with gallium and gallium-68 radionuclide was suggested. The obtained metal-polymer complex is stable over a wide range of pH values as well as in the histidine challenge reaction. In vivo distribution experiments in intact animals showed high primary accumulation of thegallium-68 MPC in blood with subsequent excretion via urinary tract.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Vp-vfa and Vp-vacopolymersmentioning

confidence: 99%

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Metal-Polymer Complexes of Gallium/Gallium-68 with Copolymers of N-Vinylpyrrolidonewith N-Vinylformamideand N-Vinyliminodiacetic Acid: A Hint for Radiolabeling of Water-Soluble Synthetic Flexible Chain Macromolecules

et al. 2020

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“…The reaction between polymer amino groups and monochloroacetic acid was carried out in KOH water solution (pH = 10) at 90 °C [ 34 , 36 ]. The content of IDA-containing groups was estimated by potentiometric titration.…”

Section: Methodsmentioning

confidence: 99%

Introduction of Re(CO)3+/99mTc(CO)3+ Organometallic Species into Vinylpyrrolidone-Allyliminodiacetate Copolymers

et al. 2021

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N-vinylpyrrolidone-co-allylamine copolymers (VP-co-AA) containing iminodiacetic (IDA) chelation units were prepared in the range of molecular masses of the copolymers from 9000 to 30,000 Da depending on polymerization conditions. Non-radioactive organometallic species Re(CO)3+ were introduced into polymeric carriers under mild conditions; the prepared metal–polymeric complexes were characterized by IR, NMR, ESI-MS and HPLC. IR spectra data confirmed the coordination of M(CO)3+ moiety to the polymeric backbone via IDA chelation unit (appearance of characteristic fac-M(CO)3+ vibrations (2005, 1890 cm−1), as well as the appearance of group of signals in 1H NMR spectra, corresponding to those inequivalent to methylene protons CH2COO (dd, 4.2 ppm), coordinated to metal ions. The optimal conditions for labeling the PVP-co-AA-IDA copolymers with radioactive 99mTc(CO)3+ species were determined. The radiochemical yields reached 97%. The obtained radiolabeled polymers were stable in blood serum for 3 h. In vivo distribution experiments in intact animals showed the high primary accumulation of technetium-99m MPC (MM = 15,000 Da) in blood with subsequent excretion via the urinary tract.

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“…To obtain MPC based on N -vinylamide copolymers, chelating fragments are introduced into copolymers during polymerization (β-diketones, acrylic acid, crotonic aldehyde) [ 41 , 42 , 43 ] or grafted to functional groups present in macromolecules via polymer-analogous reactions [ 44 , 45 ] (iminodiacetic acid, Schiff bases). Copolymers of N -vinylpyrrolidone (VP) with allylamine (AA) [ 46 ] or vinylamine (VA) [ 47 , 48 ] are convenient for modification, since they contain reactive amino groups and can be relatively easily synthesized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Water-Soluble Copolymers of N-vinylpyrrolidone with N-vinyldithiocarbamate as Multidentate Polymeric Chelation Systems and Their Complexes with Indium and Gallium

et al. 2020

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Dithiocarbamate (DTC) derivatives of N-vinylpyrrolidone-N-vinylamine (VP–VA) copolymers were synthesized via reaction between the copolymers and carbon disulfide in alkaline medium; molecular masses of the products were 12 and 29 kDa; the VP:VDTC ratios were 94:6 and 83:17 mol.%. Complexation between the obtained DTC derivatives and metal ions (indium and gallium) was investigated. It was demonstrated that metal–DTC ligand complexes with 1:3 ratio between components were formed. Gallium metal–polymer complexes (MPC) were unstable in solution. Individual indium MPC were isolated and characterized by spectral and chromatographic methods. Unlike similar gallium MPC, they appeared to be stable in histidine challenge reaction.

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Iminodiacetic acids based on vinylamine-vinylpyrrolidone copolymers

Cited by 4 publications

References 7 publications

Metal-Polymer Complexes of Gallium/Gallium-68 with Copolymers of N-Vinylpyrrolidonewith N-Vinylformamideand N-Vinyliminodiacetic Acid: A Hint for Radiolabeling of Water-Soluble Synthetic Flexible Chain Macromolecules

Metal-Polymer Complexes of Gallium/Gallium-68 with Copolymers of N-Vinylpyrrolidonewith N-Vinylformamideand N-Vinyliminodiacetic Acid: A Hint for Radiolabeling of Water-Soluble Synthetic Flexible Chain Macromolecules

Introduction of Re(CO)3+/99mTc(CO)3+ Organometallic Species into Vinylpyrrolidone-Allyliminodiacetate Copolymers

Synthesis of Water-Soluble Copolymers of N-vinylpyrrolidone with N-vinyldithiocarbamate as Multidentate Polymeric Chelation Systems and Their Complexes with Indium and Gallium

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