Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation

Jon D. Silversides; Benjamin P. Burke; Stephen J. Archibald

doi:10.1016/j.crci.2013.02.013

Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation

Jon D. Silversides, Benjamin P. Burke, Stephen J. Archibald^*

^*Corresponding author for this work

Imaging Chemistry & Biology

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Copper(II) complexes of 1,4,8,11-tetraazabicyclo[6.6.2]hexadecane (cross-bridged cyclam) derived chelators show high kinetic stability relative to less rigid non-bridged azamacrocyclic chelators and have applications as radiopharmaceuticals in PET imaging. Rapid synthesis of two novel bis-benzyl cross-bridged cyclam derivatives was achieved in 24 h compared to the typical synthesis times, between 14 and 30 days. The X-ray crystal structures are reported for the copper(II) complexes with 1,3-dibromobenzyl and tolyl derivatives revealing different ligand coordination environments. Both structures show tetradentate coordination of the tetraazamacrocycle with axial elongation along the N-Cu-N axis for the 1,3-dibromobenzyl derivative (Cu-N distances: axial av. 2.48(8) Å, equatorial av. 2.081(7) Å).

Original language	English
Pages (from-to)	524-530
Number of pages	7
Journal	COMPTES RENDUS CHIMIE
Volume	16
Issue number	6
DOIs	https://doi.org/10.1016/j.crci.2013.02.013
Publication status	Published - Jun 2013

Keywords

Coordination chemistry
Copper
Cyclam
Macrocycle
PET imaging
Radiopharmaceuticals

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10.1016/j.crci.2013.02.013

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@article{eae4071401574961a05dac9ad6cf2681,

title = "Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation",

abstract = "Copper(II) complexes of 1,4,8,11-tetraazabicyclo[6.6.2]hexadecane (cross-bridged cyclam) derived chelators show high kinetic stability relative to less rigid non-bridged azamacrocyclic chelators and have applications as radiopharmaceuticals in PET imaging. Rapid synthesis of two novel bis-benzyl cross-bridged cyclam derivatives was achieved in 24 h compared to the typical synthesis times, between 14 and 30 days. The X-ray crystal structures are reported for the copper(II) complexes with 1,3-dibromobenzyl and tolyl derivatives revealing different ligand coordination environments. Both structures show tetradentate coordination of the tetraazamacrocycle with axial elongation along the N-Cu-N axis for the 1,3-dibromobenzyl derivative (Cu-N distances: axial av. 2.48(8) {\AA}, equatorial av. 2.081(7) {\AA}).",

keywords = "Coordination chemistry, Copper, Cyclam, Macrocycle, PET imaging, Radiopharmaceuticals",

author = "Silversides, {Jon D.} and Burke, {Benjamin P.} and Archibald, {Stephen J.}",

year = "2013",

month = jun,

doi = "10.1016/j.crci.2013.02.013",

language = "English",

volume = "16",

pages = "524--530",

journal = "COMPTES RENDUS CHIMIE",

issn = "1631-0748",

publisher = "Elsevier Masson",

number = "6",

}

TY - JOUR

T1 - Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation

AU - Silversides, Jon D.

AU - Burke, Benjamin P.

AU - Archibald, Stephen J.

PY - 2013/6

Y1 - 2013/6

N2 - Copper(II) complexes of 1,4,8,11-tetraazabicyclo[6.6.2]hexadecane (cross-bridged cyclam) derived chelators show high kinetic stability relative to less rigid non-bridged azamacrocyclic chelators and have applications as radiopharmaceuticals in PET imaging. Rapid synthesis of two novel bis-benzyl cross-bridged cyclam derivatives was achieved in 24 h compared to the typical synthesis times, between 14 and 30 days. The X-ray crystal structures are reported for the copper(II) complexes with 1,3-dibromobenzyl and tolyl derivatives revealing different ligand coordination environments. Both structures show tetradentate coordination of the tetraazamacrocycle with axial elongation along the N-Cu-N axis for the 1,3-dibromobenzyl derivative (Cu-N distances: axial av. 2.48(8) Å, equatorial av. 2.081(7) Å).

AB - Copper(II) complexes of 1,4,8,11-tetraazabicyclo[6.6.2]hexadecane (cross-bridged cyclam) derived chelators show high kinetic stability relative to less rigid non-bridged azamacrocyclic chelators and have applications as radiopharmaceuticals in PET imaging. Rapid synthesis of two novel bis-benzyl cross-bridged cyclam derivatives was achieved in 24 h compared to the typical synthesis times, between 14 and 30 days. The X-ray crystal structures are reported for the copper(II) complexes with 1,3-dibromobenzyl and tolyl derivatives revealing different ligand coordination environments. Both structures show tetradentate coordination of the tetraazamacrocycle with axial elongation along the N-Cu-N axis for the 1,3-dibromobenzyl derivative (Cu-N distances: axial av. 2.48(8) Å, equatorial av. 2.081(7) Å).

KW - Coordination chemistry

KW - Copper

KW - Cyclam

KW - Macrocycle

KW - PET imaging

KW - Radiopharmaceuticals

UR - http://www.scopus.com/inward/record.url?scp=84879460187&partnerID=8YFLogxK

U2 - 10.1016/j.crci.2013.02.013

DO - 10.1016/j.crci.2013.02.013

M3 - Article

AN - SCOPUS:84879460187

SN - 1631-0748

VL - 16

SP - 524

EP - 530

JO - COMPTES RENDUS CHIMIE

JF - COMPTES RENDUS CHIMIE

IS - 6

ER -

Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex formation

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Keywords

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