X-ray crystal structure of a macrocyclic copper chelate stable enough for use in living systems: Copper(II) dihydrogen 6-(p-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate

Min K. Moi, Michael Yanuck, Shrikant V. Deshpande, Håkon Hope, Sally J. DeNardo, Claude F. Meares

Research output: Contribution to journalArticle

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Abstract

With the goal of radioimmunotherapy using copper-67 attached to monoclonal antibodies, the title complex (I) has been synthesized and shown to retain the copper ion for days under physiological conditions.10 Here we report the crystal structures of I and also of the binuclear complex dicopper(II) (6-p-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate (II). Crystals of I are triclinic, with cell dimensions a = 8.537 (4) Å, b = 8.684 (6) Å, c = 21.614 (15) Å, α = 99.48°, β = 98.69°, and γ = 90.51°; Z = 2, and space group is P1. The R value with anisotropic thermal parameters for all non-hydrogen atoms is 0.066 for 2934 reflections. In I, the Cu(II) is six-coordinate, with two axial nitrogen ligands (bond lengths 2.4 Å). The other two nitrogen atoms and two carboxylate oxygens form an approximately square plane (bond lengths 2.0 Å). Crystals of II are monoclinic, with cell dimensions a = 10.501 (3) Å, b = 9.216 (3) Å, c = 17.640 (4) Å, and β = 92.06°; Z = 2, and space group is Pc. The R value is 0.055 Å for 2650 reflections. In the binuclear complex the two coppers are pentacoordinate, and the structure is polymeric.

Original languageEnglish (US)
Pages (from-to)3458-3463
Number of pages6
JournalInorganic Chemistry
Volume26
Issue number21
StatePublished - 1987

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chelates
Copper
Crystal structure
Bond length
X rays
copper
crystal structure
Nitrogen
Atoms
Crystals
x rays
cells
antibodies
nitrogen atoms
carboxylates
crystals
Monoclonal Antibodies
Ions
Oxygen
Ligands

ASJC Scopus subject areas

  • Inorganic Chemistry

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X-ray crystal structure of a macrocyclic copper chelate stable enough for use in living systems : Copper(II) dihydrogen 6-(p-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate. / Moi, Min K.; Yanuck, Michael; Deshpande, Shrikant V.; Hope, Håkon; DeNardo, Sally J.; Meares, Claude F.

In: Inorganic Chemistry, Vol. 26, No. 21, 1987, p. 3458-3463.

Research output: Contribution to journalArticle

Moi, Min K. ; Yanuck, Michael ; Deshpande, Shrikant V. ; Hope, Håkon ; DeNardo, Sally J. ; Meares, Claude F. / X-ray crystal structure of a macrocyclic copper chelate stable enough for use in living systems : Copper(II) dihydrogen 6-(p-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate. In: Inorganic Chemistry. 1987 ; Vol. 26, No. 21. pp. 3458-3463.
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abstract = "With the goal of radioimmunotherapy using copper-67 attached to monoclonal antibodies, the title complex (I) has been synthesized and shown to retain the copper ion for days under physiological conditions.10 Here we report the crystal structures of I and also of the binuclear complex dicopper(II) (6-p-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetraacetate (II). Crystals of I are triclinic, with cell dimensions a = 8.537 (4) {\AA}, b = 8.684 (6) {\AA}, c = 21.614 (15) {\AA}, α = 99.48°, β = 98.69°, and γ = 90.51°; Z = 2, and space group is P1. The R value with anisotropic thermal parameters for all non-hydrogen atoms is 0.066 for 2934 reflections. In I, the Cu(II) is six-coordinate, with two axial nitrogen ligands (bond lengths 2.4 {\AA}). The other two nitrogen atoms and two carboxylate oxygens form an approximately square plane (bond lengths 2.0 {\AA}). Crystals of II are monoclinic, with cell dimensions a = 10.501 (3) {\AA}, b = 9.216 (3) {\AA}, c = 17.640 (4) {\AA}, and β = 92.06°; Z = 2, and space group is Pc. The R value is 0.055 {\AA} for 2650 reflections. In the binuclear complex the two coppers are pentacoordinate, and the structure is polymeric.",
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AU - Moi, Min K.

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AU - Meares, Claude F.

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