Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores. Crystal and molecular structures of [ReBr(CO)3(H2NCH2 C5H4N)], [Re(CO)3{(C5H4 NCH2)2NH}]Br,

Sangeeta Ray, Murali K. Levadala, Neva Lazarova, Lihui Wei, John F. Valliant, Karin A. Stephenson, John W. Babich, Kevin P. Maresca, Jon Zubieta

Research output: Contribution to journalArticle

Abstract

The reactions of a series of potentially tridentate ligands, derived from single amino acids or amino acid analogues, with [NEt4]2[ReBr3(CO)3] have been investigated. The model compounds [Re(CO)3Br{(2-pyridylmethyl)NH2}] (1) and [Re-(CO)3{(2-pyridylmethyl)2NH}]Br (2) were also prepared and structurally characterized. With ligands possessing two pyridyl appendages, (2-pyridylmethyl)2NX (X = -CH2CO2H, -CH2CO2Et, -CH2CH2CO2H, -CH2CH2CO2Et, -CH2CH2CH2CH2-CH (NHCO2Bu)CO2H), complexes of the type [Re(CO)3(ligand)]Br (3-6) were isolated. All possess the fac-{Re(CO)3N3} coordination geometry in the cationic molecular unit. Similarly, the ligands with the imidazolyl arms (2-pyridylmethyl) {2-(1-methylimidazolyl)methyl}NCH2CO2Et and {2-(1-methylimidazolyl)methyl}2NCH2CO2Et, complexes 7 and 8 of the same [Re(CO)3(ligand)]Br type, were prepared. Replacement of one pyridyl arm with a thiophene group yielded the complex [Re(CO)3{(2-pyridylmethyl)N(CH2 CO2)(2-thiophenemethyl)}] (9), while additional substitution of X = -H for -CH2CO2H yielded [Re(CO)3Br{(2-pyridylmethyl)NH(2-thiophenemethyl)}] (10). In both 9 and 10, the thiophene is uncoordinated and pendant, and the derivatives display fac-{Re(CO)3N2O} and fac-{Re(CO)3N2Br} coordination geometries, respectively. Crystal data: C9H8BrN2O3Re (1), triclinic P1̄, a = 8.156(1) Å, b = 12.077(1) Å, c = 12.945(2) Å, α = 92.183(3)°, β = 107.848(3)°, γ = 100.955(7)°, V = 1185.1(3) Å, Z = 4; C15H13BrN3O3Re (2), tetragonal P41, a = 8.6095(3) Å, c = 22.228(1) Å, V = 1646.9(1) Å3, Z = 4; C17H14BrN3O5Re ·CH3OH (3), monoclinic P21/m, a = 7.4425(3) Å, b = 9.7596(4) Å, c = 14.0646(6) Å, β = 97.753(1)°, V = 1012.26(7) Å3, Z = 2; C19H19BrN3O5Re (4), tetragonal P421c, a = 16.895(3) Å, c = 15.042(3) Å, V = 4293.7(13) Å3, Z = 8; C18H20BrN4O5Re ·CH3OH·H2O (7), monoclinic P21/c, a = 10.2816(4) Å, b = 30.386(1) Å, c = 14.5810(6) Å, β = 99.868(1)°, V = 4488.03(3) Å3, Z = 8; C17H21BrN5O5Re ·0.5CH2Cl2·0.5H2O (8), triclinic P1̄, a = 11.5363(6) Å, b = 13.1898(6) Å, c = 16.4933(8) Å α = 89.356(1)°, β = 74.907(1)°, γ = 76.216(1)°, V = 2349.8(2) Å3, Z = 4; C16H13N2O5ReS (9), monoclinic P21/c, a = 17.2072(7) Å, b = 8.5853(4) Å, c = 11.5607(5) Å, β = 101.73(1)°, V = 1672.2(1) Å3, Z= 4; and C14H12N2O3BrReS (10), triclinic P1̄, a = 7.5585(3) Å, b = 9.7713(4) Å, c = 11.7103(4) Å, α = 109.566(1)°, β = 98.298(1)°, γ = 100.925(1)°, V = 779.73(5) Å3, Z = 2.

Original languageEnglish (US)
Pages (from-to)6417-6425
Number of pages9
JournalInorganic Chemistry
Volume41
Issue number24
DOIs
StatePublished - Dec 2 2002
Externally publishedYes

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Biomolecules
chelates
Labeling
Molecular structure
marking
amino acids
molecular structure
Crystal structure
Ligands
Amino Acids
ligands
crystal structure
Thiophenes
thiophenes
appendages
Geometry
geometry
Substitution reactions
methylidyne
substitutes

ASJC Scopus subject areas

  • Inorganic Chemistry

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Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores. Crystal and molecular structures of [ReBr(CO)3(H2NCH2 C5H4N)], [Re(CO)3{(C5H4 NCH2)2NH}]Br, / Ray, Sangeeta; Levadala, Murali K.; Lazarova, Neva; Wei, Lihui; Valliant, John F.; Stephenson, Karin A.; Babich, John W.; Maresca, Kevin P.; Zubieta, Jon.

In: Inorganic Chemistry, Vol. 41, No. 24, 02.12.2002, p. 6417-6425.

Research output: Contribution to journalArticle

Ray, Sangeeta ; Levadala, Murali K. ; Lazarova, Neva ; Wei, Lihui ; Valliant, John F. ; Stephenson, Karin A. ; Babich, John W. ; Maresca, Kevin P. ; Zubieta, Jon. / Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores. Crystal and molecular structures of [ReBr(CO)3(H2NCH2 C5H4N)], [Re(CO)3{(C5H4 NCH2)2NH}]Br,. In: Inorganic Chemistry. 2002 ; Vol. 41, No. 24. pp. 6417-6425.
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title = "Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores. Crystal and molecular structures of [ReBr(CO)3(H2NCH2 C5H4N)], [Re(CO)3{(C5H4 NCH2)2NH}]Br,",
abstract = "The reactions of a series of potentially tridentate ligands, derived from single amino acids or amino acid analogues, with [NEt4]2[ReBr3(CO)3] have been investigated. The model compounds [Re(CO)3Br{(2-pyridylmethyl)NH2}] (1) and [Re-(CO)3{(2-pyridylmethyl)2NH}]Br (2) were also prepared and structurally characterized. With ligands possessing two pyridyl appendages, (2-pyridylmethyl)2NX (X = -CH2CO2H, -CH2CO2Et, -CH2CH2CO2H, -CH2CH2CO2Et, -CH2CH2CH2CH2-CH (NHCO2Bu)CO2H), complexes of the type [Re(CO)3(ligand)]Br (3-6) were isolated. All possess the fac-{Re(CO)3N3} coordination geometry in the cationic molecular unit. Similarly, the ligands with the imidazolyl arms (2-pyridylmethyl) {2-(1-methylimidazolyl)methyl}NCH2CO2Et and {2-(1-methylimidazolyl)methyl}2NCH2CO2Et, complexes 7 and 8 of the same [Re(CO)3(ligand)]Br type, were prepared. Replacement of one pyridyl arm with a thiophene group yielded the complex [Re(CO)3{(2-pyridylmethyl)N(CH2 CO2)(2-thiophenemethyl)}] (9), while additional substitution of X = -H for -CH2CO2H yielded [Re(CO)3Br{(2-pyridylmethyl)NH(2-thiophenemethyl)}] (10). In both 9 and 10, the thiophene is uncoordinated and pendant, and the derivatives display fac-{Re(CO)3N2O} and fac-{Re(CO)3N2Br} coordination geometries, respectively. Crystal data: C9H8BrN2O3Re (1), triclinic P1̄, a = 8.156(1) {\AA}, b = 12.077(1) {\AA}, c = 12.945(2) {\AA}, α = 92.183(3)°, β = 107.848(3)°, γ = 100.955(7)°, V = 1185.1(3) {\AA}, Z = 4; C15H13BrN3O3Re (2), tetragonal P41, a = 8.6095(3) {\AA}, c = 22.228(1) {\AA}, V = 1646.9(1) {\AA}3, Z = 4; C17H14BrN3O5Re ·CH3OH (3), monoclinic P21/m, a = 7.4425(3) {\AA}, b = 9.7596(4) {\AA}, c = 14.0646(6) {\AA}, β = 97.753(1)°, V = 1012.26(7) {\AA}3, Z = 2; C19H19BrN3O5Re (4), tetragonal P421c, a = 16.895(3) {\AA}, c = 15.042(3) {\AA}, V = 4293.7(13) {\AA}3, Z = 8; C18H20BrN4O5Re ·CH3OH·H2O (7), monoclinic P21/c, a = 10.2816(4) {\AA}, b = 30.386(1) {\AA}, c = 14.5810(6) {\AA}, β = 99.868(1)°, V = 4488.03(3) {\AA}3, Z = 8; C17H21BrN5O5Re ·0.5CH2Cl2·0.5H2O (8), triclinic P1̄, a = 11.5363(6) {\AA}, b = 13.1898(6) {\AA}, c = 16.4933(8) {\AA} α = 89.356(1)°, β = 74.907(1)°, γ = 76.216(1)°, V = 2349.8(2) {\AA}3, Z = 4; C16H13N2O5ReS (9), monoclinic P21/c, a = 17.2072(7) {\AA}, b = 8.5853(4) {\AA}, c = 11.5607(5) {\AA}, β = 101.73(1)°, V = 1672.2(1) {\AA}3, Z= 4; and C14H12N2O3BrReS (10), triclinic P1̄, a = 7.5585(3) {\AA}, b = 9.7713(4) {\AA}, c = 11.7103(4) {\AA}, α = 109.566(1)°, β = 98.298(1)°, γ = 100.925(1)°, V = 779.73(5) {\AA}3, Z = 2.",
author = "Sangeeta Ray and Levadala, {Murali K.} and Neva Lazarova and Lihui Wei and Valliant, {John F.} and Stephenson, {Karin A.} and Babich, {John W.} and Maresca, {Kevin P.} and Jon Zubieta",
year = "2002",
month = "12",
day = "2",
doi = "10.1021/ic020476e",
language = "English (US)",
volume = "41",
pages = "6417--6425",
journal = "Inorganic Chemistry",
issn = "0020-1669",
publisher = "American Chemical Society",
number = "24",

}

TY - JOUR

T1 - Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores. Crystal and molecular structures of [ReBr(CO)3(H2NCH2 C5H4N)], [Re(CO)3{(C5H4 NCH2)2NH}]Br,

AU - Ray, Sangeeta

AU - Levadala, Murali K.

AU - Lazarova, Neva

AU - Wei, Lihui

AU - Valliant, John F.

AU - Stephenson, Karin A.

AU - Babich, John W.

AU - Maresca, Kevin P.

AU - Zubieta, Jon

PY - 2002/12/2

Y1 - 2002/12/2

N2 - The reactions of a series of potentially tridentate ligands, derived from single amino acids or amino acid analogues, with [NEt4]2[ReBr3(CO)3] have been investigated. The model compounds [Re(CO)3Br{(2-pyridylmethyl)NH2}] (1) and [Re-(CO)3{(2-pyridylmethyl)2NH}]Br (2) were also prepared and structurally characterized. With ligands possessing two pyridyl appendages, (2-pyridylmethyl)2NX (X = -CH2CO2H, -CH2CO2Et, -CH2CH2CO2H, -CH2CH2CO2Et, -CH2CH2CH2CH2-CH (NHCO2Bu)CO2H), complexes of the type [Re(CO)3(ligand)]Br (3-6) were isolated. All possess the fac-{Re(CO)3N3} coordination geometry in the cationic molecular unit. Similarly, the ligands with the imidazolyl arms (2-pyridylmethyl) {2-(1-methylimidazolyl)methyl}NCH2CO2Et and {2-(1-methylimidazolyl)methyl}2NCH2CO2Et, complexes 7 and 8 of the same [Re(CO)3(ligand)]Br type, were prepared. Replacement of one pyridyl arm with a thiophene group yielded the complex [Re(CO)3{(2-pyridylmethyl)N(CH2 CO2)(2-thiophenemethyl)}] (9), while additional substitution of X = -H for -CH2CO2H yielded [Re(CO)3Br{(2-pyridylmethyl)NH(2-thiophenemethyl)}] (10). In both 9 and 10, the thiophene is uncoordinated and pendant, and the derivatives display fac-{Re(CO)3N2O} and fac-{Re(CO)3N2Br} coordination geometries, respectively. Crystal data: C9H8BrN2O3Re (1), triclinic P1̄, a = 8.156(1) Å, b = 12.077(1) Å, c = 12.945(2) Å, α = 92.183(3)°, β = 107.848(3)°, γ = 100.955(7)°, V = 1185.1(3) Å, Z = 4; C15H13BrN3O3Re (2), tetragonal P41, a = 8.6095(3) Å, c = 22.228(1) Å, V = 1646.9(1) Å3, Z = 4; C17H14BrN3O5Re ·CH3OH (3), monoclinic P21/m, a = 7.4425(3) Å, b = 9.7596(4) Å, c = 14.0646(6) Å, β = 97.753(1)°, V = 1012.26(7) Å3, Z = 2; C19H19BrN3O5Re (4), tetragonal P421c, a = 16.895(3) Å, c = 15.042(3) Å, V = 4293.7(13) Å3, Z = 8; C18H20BrN4O5Re ·CH3OH·H2O (7), monoclinic P21/c, a = 10.2816(4) Å, b = 30.386(1) Å, c = 14.5810(6) Å, β = 99.868(1)°, V = 4488.03(3) Å3, Z = 8; C17H21BrN5O5Re ·0.5CH2Cl2·0.5H2O (8), triclinic P1̄, a = 11.5363(6) Å, b = 13.1898(6) Å, c = 16.4933(8) Å α = 89.356(1)°, β = 74.907(1)°, γ = 76.216(1)°, V = 2349.8(2) Å3, Z = 4; C16H13N2O5ReS (9), monoclinic P21/c, a = 17.2072(7) Å, b = 8.5853(4) Å, c = 11.5607(5) Å, β = 101.73(1)°, V = 1672.2(1) Å3, Z= 4; and C14H12N2O3BrReS (10), triclinic P1̄, a = 7.5585(3) Å, b = 9.7713(4) Å, c = 11.7103(4) Å, α = 109.566(1)°, β = 98.298(1)°, γ = 100.925(1)°, V = 779.73(5) Å3, Z = 2.

AB - The reactions of a series of potentially tridentate ligands, derived from single amino acids or amino acid analogues, with [NEt4]2[ReBr3(CO)3] have been investigated. The model compounds [Re(CO)3Br{(2-pyridylmethyl)NH2}] (1) and [Re-(CO)3{(2-pyridylmethyl)2NH}]Br (2) were also prepared and structurally characterized. With ligands possessing two pyridyl appendages, (2-pyridylmethyl)2NX (X = -CH2CO2H, -CH2CO2Et, -CH2CH2CO2H, -CH2CH2CO2Et, -CH2CH2CH2CH2-CH (NHCO2Bu)CO2H), complexes of the type [Re(CO)3(ligand)]Br (3-6) were isolated. All possess the fac-{Re(CO)3N3} coordination geometry in the cationic molecular unit. Similarly, the ligands with the imidazolyl arms (2-pyridylmethyl) {2-(1-methylimidazolyl)methyl}NCH2CO2Et and {2-(1-methylimidazolyl)methyl}2NCH2CO2Et, complexes 7 and 8 of the same [Re(CO)3(ligand)]Br type, were prepared. Replacement of one pyridyl arm with a thiophene group yielded the complex [Re(CO)3{(2-pyridylmethyl)N(CH2 CO2)(2-thiophenemethyl)}] (9), while additional substitution of X = -H for -CH2CO2H yielded [Re(CO)3Br{(2-pyridylmethyl)NH(2-thiophenemethyl)}] (10). In both 9 and 10, the thiophene is uncoordinated and pendant, and the derivatives display fac-{Re(CO)3N2O} and fac-{Re(CO)3N2Br} coordination geometries, respectively. Crystal data: C9H8BrN2O3Re (1), triclinic P1̄, a = 8.156(1) Å, b = 12.077(1) Å, c = 12.945(2) Å, α = 92.183(3)°, β = 107.848(3)°, γ = 100.955(7)°, V = 1185.1(3) Å, Z = 4; C15H13BrN3O3Re (2), tetragonal P41, a = 8.6095(3) Å, c = 22.228(1) Å, V = 1646.9(1) Å3, Z = 4; C17H14BrN3O5Re ·CH3OH (3), monoclinic P21/m, a = 7.4425(3) Å, b = 9.7596(4) Å, c = 14.0646(6) Å, β = 97.753(1)°, V = 1012.26(7) Å3, Z = 2; C19H19BrN3O5Re (4), tetragonal P421c, a = 16.895(3) Å, c = 15.042(3) Å, V = 4293.7(13) Å3, Z = 8; C18H20BrN4O5Re ·CH3OH·H2O (7), monoclinic P21/c, a = 10.2816(4) Å, b = 30.386(1) Å, c = 14.5810(6) Å, β = 99.868(1)°, V = 4488.03(3) Å3, Z = 8; C17H21BrN5O5Re ·0.5CH2Cl2·0.5H2O (8), triclinic P1̄, a = 11.5363(6) Å, b = 13.1898(6) Å, c = 16.4933(8) Å α = 89.356(1)°, β = 74.907(1)°, γ = 76.216(1)°, V = 2349.8(2) Å3, Z = 4; C16H13N2O5ReS (9), monoclinic P21/c, a = 17.2072(7) Å, b = 8.5853(4) Å, c = 11.5607(5) Å, β = 101.73(1)°, V = 1672.2(1) Å3, Z= 4; and C14H12N2O3BrReS (10), triclinic P1̄, a = 7.5585(3) Å, b = 9.7713(4) Å, c = 11.7103(4) Å, α = 109.566(1)°, β = 98.298(1)°, γ = 100.925(1)°, V = 779.73(5) Å3, Z = 2.

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