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Investigation of the Coordination Interactions of S-(Pyridin-2-ylmethyl)-L-Cysteine Ligands with M(CO)3+ (M=Re, 99mTc).
- Source :
-
Inorganic Chemistry . 11/16/2009, Vol. 48 Issue 22, p10625-10634. 10p. 9 Diagrams, 3 Charts, 4 Graphs. - Publication Year :
- 2009
-
Abstract
- Development of new ligands for fac-M(OH2)3(CO)3+ (M = Re, 99mTc) led the investigation with S-(pyridin-2-ylmethyl)- L-cysteine, 1. The ligand 1 has potential to coordinate with the metal through three different tridentate modes: tripodal through cysteine (O,N,S) and two linear involving the S-pyridyl and cysteine (O,S,Npy, N,S,Npy). From the reaction with 1, two species were observed in the 1H NMR, where the primary product was the linear fac-Re(N,S, Npy-1)(CO)3, 2a, complex. To identity the coordination mode of the minor product, functionalized analogues of 1 were prepared from S-(pyridln-2-ylmethyl)-Boc-L-cysteine-methyl ester, 3, with orthogonal protecting groups on the C terminus (methyl ester) in S-(pyridin-2-ylmethyl)-L-cysteine methyl ester, 4, or N terminus (Boc) in S-(pyridin2-ylmethyl)-Boc-L-cysteine, 6, that specifically directed the coordination mode of fac-M(H20)3(CO)3+ to either N,S, Npy or O,S,Npy, respectively. Two diastereomers [fac-Re(CO)3(N,S,Npy-4)]+, 5a and 5b, were observed and independently characterized by X-ray structure analysis and NMR in high yield with 4. Surprisingly, the O,S,Npy Re complex with ligand 6 was not observed and simplified versions, 3-(pyridin-2-ylmethylthio) propanoic acid, 7, and 2-(pyridin-2-ylmethylthio)acetic acid, 8, were investigated. Ligand 7 did not yield the desired linear tridentate O,S,Npy product. However, the shorter ligand 8 formed fac-Re(CO)3(O,S,Npy-8), 9, in high yield. 99mTc labeling studies were conducted and yielded similar results to the rhenium complex and effective (>99%) at 10-5 M ligand concentration. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00201669
- Volume :
- 48
- Issue :
- 22
- Database :
- Academic Search Index
- Journal :
- Inorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 45661080
- Full Text :
- https://doi.org/10.1021/ic901159r