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用于用[Tc(CO)(3)]⁺和[Re(CO)(3)]⁺核心标记生物分子的双功能单氨基酸螯合物。[ReBr(CO)(3)(H₂NCH₂C₅H₄N)]、[Re(CO)(3)[(C₅H₄NCH₂)₂NH]]Br、[Re(CO)(3)[(C₅H₄NCH₂)₂NCH₂CO₂H]]Br、[Re(CO)(3)[X(Y)NCH₂CO₂CH₂CH₃]]Br（X = Y = 2-吡啶基甲基；X = 2-吡啶基甲基，Y = 2-(1-甲基咪唑基)甲基；X = Y = 2-(1-甲基咪唑基)甲基）、[ReBr(CO)(3)[(C₅H₄NCH₂)NH(CH₂C₄H₃S)]]和[Re(CO)(3)[(C₅H₄NCH₂)N(CH₂C₄H₃S)(CH₂CO₂)]]的晶体和分子结构

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)(H(2)NCH(2)C(5)H(4)N)], [Re(CO)(3)[(C(5)H(4)NCH(2))(2)NH]]Br, [Re(CO)(3)[(C(5)H(4)NCH(2))(2)NCH(2)CO(2)H]]Br, [Re(CO)(3)[X(Y)NCH(2)CO(2)CH(2)CH(3)]]Br (X = Y = 2-pyridylmethyl; X = 2-pyridylmethyl, Y = 2-(1-methylimidazolyl)methyl; X = Y = 2-(1-methylimidazolyl)methyl), [ReBr(CO)(3)[(C(5)H(4)NCH(2))NH(CH(2)C(4)H(3)S)]], and [Re(CO)(3)[(C(5)H(4)NCH(2))N(CH(2)C(4)H(3)S)(CH(2)CO(2))]].

作者信息

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

机构信息

Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA.

出版信息

Inorg Chem. 2002 Dec 2;41(24):6417-25. doi: 10.1021/ic020476e.

DOI:10.1021/ic020476e
PMID:12444786
Abstract

The reactions of a series of potentially tridentate ligands, derived from single amino acids or amino acid analogues, with NEt(4)[ReBr(3)(CO)(3)] have been investigated. The model compounds [Re(CO)(3)Br[(2-pyridylmethyl)NH(2)]] (1) and [Re(CO)(3)[(2-pyridylmethyl)(2)NH]]Br (2) were also prepared and structurally characterized. With ligands possessing two pyridyl appendages, (2-pyridylmethyl)(2)NX (X = -CH(2)CO(2)H, -CH(2)CO(2)Et, -CH(2)CH(2)CO(2)H, -CH(2)CH(2)CO(2)Et, -CH(2)CH(2)CH(2)CH(2)CH(NHCO(2)(t)Bu)CO(2)H), complexes of the type [Re(CO)(3)(ligand)]Br (3-6) were isolated. All possess the fac-[Re(CO)(3)N(3)] coordination geometry in the cationic molecular unit. Similarly, the ligands with the imidazolyl arms (2-pyridylmethyl)[2-(1-methylimidazolyl)methyl]NCH(2)CO(2)Et and 2-(1-methylimidazolyl)methylNCH(2)CO(2)Et, 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(CH(2)CO(2))(2-thiophenemethyl)]] (9), while additional substitution of X = -H for -CH(2)CO(2)H yielded [Re(CO)(3)Br[(2-pyridylmethyl)NH(2-thiophenemethyl)]] (10). In both 9 and 10, the thiophene is uncoordinated and pendant, and the derivatives display fac-[Re(CO)(3)N(2)O] and fac-[Re(CO)(3)N(2)Br] coordination geometries, respectively. Crystal data: C(9)H(8)BrN(2)O(3)Re (1), triclinic P1, a = 8.156(1) A, b = 12.077(1) A, c = 12.945(2) A, alpha = 92.183(3) degrees, beta = 107.848(3) degrees, gamma = 100.955(7) degrees, V = 1185.1(3) A, Z = 4; C(15)H(13)BrN(3)O(3)Re (2), tetragonal P4(1), a = 8.6095(3) A, c = 22.228(1) A, V = 1646.9(1) A(3), Z = 4; C(17)H(14)BrN(3)O(5)Re.CH(3)OH (3), monoclinic P2(1)/m, a = 7.4425(3) A, b = 9.7596(4) A, c = 14.0646(6) A, beta = 97.753(1) degrees, V = 1012.26(7) A(3), Z = 2; C(19)H(19)BrN(3)O(5)Re (4), tetragonal P42(1)c, a = 16.895(3) A, c = 15.042(3) A, V = 4293.7(13) A(3), Z = 8; C(18)H(20)BrN(4)O(5)Re.CH(3)OH.H(2)O (7), monoclinic P2(1)/c, a = 10.2816(4) A, b = 30.386(1) A, c = 14.5810(6) A, beta = 99.868(1) degrees, V = 4488.03(3) A(3), Z = 8; C(17)H(21)BrN(5)O(5)Re.0.5CH(2)Cl(2).0.5H(2)O (8), triclinic P1, a = 11.5363(6) A, b = 13.1898(6) A, c = 16.4933(8) A, alpha = 89.356(1) degrees, beta = 74.907(1) degrees, gamma = 76.216(1) degrees, V = 2349.8(2) A(3), Z = 4; C(16)H(13)N(2)O(5)ReS (9), monoclinic P2(1)/c, a = 17.2072(7) A, b = 8.5853(4) A, c = 11.5607(5) A, beta = 101.73(1) degrees, V = 1672.2(1) A(3), Z = 4; and C(14)H(12)N(2)O(3)BrReS (10), triclinic P1, a = 7.5585(3) A, b = 9.7713(4) A, c = 11.7103(4) A, alpha = 109.566(1) degrees, beta = 98.298(1) degrees, gamma = 100.925(1) degrees, V = 779.73(5) A(3), Z = 2.

摘要

研究了一系列由单个氨基酸或氨基酸类似物衍生而来的潜在三齿配体与NEt(4)[ReBr(3)(CO)(3)]的反应。还制备并对模型化合物[Re(CO)(3)Br[(2-吡啶基甲基)NH(2)]] (1)和[Re(CO)(3)[(2-吡啶基甲基)(2)NH]]Br (2)进行了结构表征。对于具有两个吡啶基附属基团的配体(2-吡啶基甲基)(2)NX（X = -CH(2)CO(2)H、-CH(2)CO(2)Et、-CH(2)CH(2)CO(2)H、-CH(2)CH(2)CO(2)Et、-CH(2)CH(2)CH(2)CH(2)CH(NHCO(2)(t)Bu)CO(2)H），分离出了[Re(CO)(3)(配体)]Br类型的配合物(3 - 6)。在阳离子分子单元中，它们均具有面式-[Re(CO)(3)N(3)]配位几何结构。类似地，制备了带有咪唑基臂的配体(2-吡啶基甲基)[2-(1-甲基咪唑基)甲基]NCH(2)CO(2)Et和2-(1-甲基咪唑基)甲基NCH(2)CO(2)Et，即相同[Re(CO)(3)(配体)]Br类型的配合物7和8。用噻吩基团取代一个吡啶基臂得到配合物[Re(CO)(3)[(2-吡啶基甲基)N(CH(2)CO(2))(2-噻吩甲基)]] (9)，而将X = -H额外取代-CH(2)CO(2)H得到[Re(CO)(3)Br[(2-吡啶基甲基)NH(2-噻吩甲基)]] (10)。在9和10中，噻吩均未配位且呈悬垂状，衍生物分别呈现出面式-[Re(CO)(3)N(2)O]和面式-[Re(CO)(3)N(2)Br]配位几何结构。晶体数据：C(9)H(8)BrN(2)O(3)Re (1)，三斜晶系P1，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；C(15)H(13)BrN(3)O(3)Re (2)，四方晶系P4(1)，a = 8.6095(3) Å，c = 22.228(1) Å，V = 1646.9(1) Å(3)，Z = 4；C(17)H(14)BrN(3)O(5)Re.CH( )OH (3)，单斜晶系P2(1)/m，a = 7.4425(3) Å，b = 9.7596(4) Å，c = 14.0646(6) Å，β = 97.753(1)°，V = 1012.26(7) Å(3)，Z = 2；C(19)H(19)BrN(3)O(5)Re (4)，四方晶系P42(1)c，a = 16.895(3) Å，c = 15.042(3) Å，V = 4293.7(13) Å(3)，Z = 8；C(18)H(20)BrN(4)O(5)Re.CH( )OH.H( )O (7)，单斜晶系P2(1)/c，a = 10.2816(4) Å，b = 30.386(1) Å，c = 14.5810(6) Å，β = 99.868(1)°，V = 4488.03(3) Å(3)，Z = 8；C(17)H(21)BrN(5)O(5)Re.0.5CH(2)Cl(2).

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