X-ray structural study of organic ligands of the complexone type. III. Crystal and molecular structure of phosphonomethylglycine and iminodiacetic-monomethylphosphonic acid

Shkol'nikova, L. M.; Porai-Koshits, M. A.; Dyatlova, N. M.; Yaroshenko, G. F.; Rudomino, M. V.; Kolova, E. K.

doi:10.1007/bf00746199

Cited by 16 publications

(15 citation statements)

References 13 publications

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“…The N-(phosphonomethyl)iminodiacetic acid (PMIDAH 4 , 1) ligand is an analog of NTAH 3 with a phosphonate group in place of one of the three carboxylates of NTAH 3 (Scheme 1). The PMIDAH 4 ligand possesses four acidic protons capable of deprotonation at pH values indicated in Figure 1 [37,38]. Like NTAH 3 , 1 is a potential tetradentate ligand and is expected to bind as a tridentate ligand to form a robust mononuclear complex (Scheme 1, Eq.…”

Section: Resultsmentioning

confidence: 99%

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fac-99mTc/Re-tricarbonyl complexes with tridentate aminocarboxyphosphonate ligands: Suitability of the phosphonate group in chelate ligand design of new imaging agents

Lipowska

Klenc

Taylor

et al. 2019

Inorganica Chimica Acta

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Ligands that coordinate via dianionic phosphonate groups have not been widely utilized in radiopharmaceuticals. N-(phosphonomethyl)iminodiacetic acid (1, PMIDA) and N-(phosphonomethyl)glycine (2, PMG) were investigated as new chelators for the 99m Tc/Retricarbonyl "core" (fac-M(CO) 3 , M = 99m Tc, Re) present in a major class of radiopharmaceuticals. fac-M(CO) 3 (PMIDA) and fac-M(CO) 3 (PMG) complexes were studied by HPLC and 1 H/ 13 C/ 31 P NMR methods for M = Re (Re-1 and Re-2) and by HPLC for M = 99m Tc (99m Tc-1 and 99m Tc-2). Re-1 and 99m Tc-1 complexes exhibit a similar pH-dependent equilibrium between geometric linkage isomers (M-1a and M-1b). However, only one isomer exists for M-2 under all conditions. Structural characterization by X-ray crystallography reveals the presence of a bond between a phosphonate oxygen and the Re(I) center in fac-Re(CO) 3 (PMG) (Re-2). Detailed comparisons of NMR data for Re-2 conclusively demonstrate that the phosphonate group is coordinated in Re-1b (isomer favored at high pH) but not in Re-1a, which has a dangling N-(phosphonomethyl) group. To our knowledge, Re-1b and Re-2 and their 99m Tc analogs are the first well-documented examples of complexes with these metal-tricarbonyl cores having a dianionic phosphonate group directly coordinated in a fac-M(CO) 3-O-P grouping. Pharmacokinetic studies using Sprague-Dawley rats reveal that 99m Tc-2 is a robust tracer. Hence, phosphonate groups should be considered in designing 99m Tc and 186/188 Re radiopharmaceuticals, including agents with bioactive moieties attached to dangling carboxylate or phosphonate groups.

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Section: Resultsmentioning

confidence: 99%

“…Most prevalent protonation states of PMIDAH 4 at various pH ranges, according to the previously reported pKa data [37,38]. Table 1.…”

Section: Figurementioning

confidence: 94%

fac-99mTc/Re-tricarbonyl complexes with tridentate aminocarboxyphosphonate ligands: Suitability of the phosphonate group in chelate ligand design of new imaging agents

Lipowska

Klenc

Taylor

et al. 2019

Inorganica Chimica Acta

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“…Part of the crystal structure of BOWJIG (Shkol'nikova et al, 1982), showing the formation of a (110) sheet built from four types of centrosymmetric ring. For the sake of clarity, H atoms bonded to C atoms have been omitted.…”

Section: Figurementioning

confidence: 99%

“…In view of the two-dimensional supramolecular structure of (I), it is of interest to compare this with the structure of the acid component itself, (II) [Cambridge Structural Database (CSD; Allen & Kennard, 1993) reference code BOWJIG (Shkol'nikova et al, 1982)], which crystallizes in space group P1. The CSD entry for BOWJIG lists coordinates for only nine of the ten H atoms and notes that the coordinates for the H atom on one of the carboxyl atoms, O4, have been omitted The molecular components of compound (I), showing the atom-labelling scheme.…”

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confidence: 99%

Self-assembled hydrogen-bonded bilayers in 1,4-diazabicyclo[2.2.2]octane–N-(phosphonomethyl)iminodiacetic acid–water (1/1/1.5)

et al. 2002

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The title compound is a hydrated salt, 1,4-diazoniabicyclo[2.2.2]octane-N-[(hydroxyphosphinato)methyl]iminiodiacetate-water (1/1/1.5), C(6)H(14)N(2)(2+).C(5)H(8)NO(7)P(2-).1.5H(2)O, in which one of the water molecules lies across a twofold rotation axis in space group P2/n. The ionic components are linked into sheets by a combination of a three-centre N-H...(O)(2) hydrogen bond and two-centre O-H...O and N-H...O hydrogen bonds, and these sheets are pairwise linked by the water molecules into bilayers, by means of further O-H...O hydrogen bonds.

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“…In addition to herbicidal properties, glyphosate is also known to be an effective chelating agent (Glass, 1984; Shkol'nikova et al, 1982; Toy and Uhling, 1964). Thelen et al (1995a) found that cations such as Ca +2 and Mg +2 associate with both the carboxyl and phosphonate functional groups of glyphosate to form a structured chelate complex in herbicide solutions.…”

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confidence: 99%

Yield Environment Affects Glyphosate‐Resistant Hybrid Response to Glyphosate

Thelen

Penner

2007

Crop Science

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The yield response of glyphosate‐resistant corn (Zea mays L.) to glyphosate across a broad range of temporal yield environments is not well understood. Field experiments were conducted at three Michigan locations over a five year period (2002–2006) comparing corn grain yield of glyphosate‐resistant hybrids as affected by a glyphosate‐based or conventional herbicide system. Regression analyses of yield data showed a dual glyphosate‐resistant hybrid yield response to glyphosate based on the temporal yield environment for a given year. Under average‐ to low‐yield environments, the glyphosate‐based herbicide system resulted in greater grain yield. However, under temporal high yield environments, the conventional herbicide system resulted in greater grain yield. Threshold corn grain yields above which the conventional herbicide system resulted in higher grain yield and below which the glyphosate‐based herbicide system resulted in higher grain yield were determined to be: 11.38 (± 0.13), 12.73 (± 0.14), 13.97 (± 0.25), and 11.62 (± 0.10) Mg ha−1 respectively for the Huron, Montcalm, Saginaw, and combined site average. Differences in weed control levels were not observed and weed control did not appear to be a factor in grain yield determination. The results suggest a slight corn grain yield reduction from glyphosate under certain temporal high‐yield environments.

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X-ray structural study of organic ligands of the complexone type. III. Crystal and molecular structure of phosphonomethylglycine and iminodiacetic-monomethylphosphonic acid

Cited by 16 publications

References 13 publications

fac-99mTc/Re-tricarbonyl complexes with tridentate aminocarboxyphosphonate ligands: Suitability of the phosphonate group in chelate ligand design of new imaging agents

fac-99mTc/Re-tricarbonyl complexes with tridentate aminocarboxyphosphonate ligands: Suitability of the phosphonate group in chelate ligand design of new imaging agents

Self-assembled hydrogen-bonded bilayers in 1,4-diazabicyclo[2.2.2]octane–N-(phosphonomethyl)iminodiacetic acid–water (1/1/1.5)

Yield Environment Affects Glyphosate‐Resistant Hybrid Response to Glyphosate

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