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Expanding the Cyclopentadienyl Framework: 99mTc/Re Complexes with Orthogonal Functions for Bioconjugation


Lengacher, Raphael; Csucker, Joshua; Hernández-Valdés, Daniel; Spingler, Bernhard; Braband, Henrik; Alberto, Roger (2021). Expanding the Cyclopentadienyl Framework: 99mTc/Re Complexes with Orthogonal Functions for Bioconjugation. Bioconjugate Chemistry, 32(7):1393-1398.

Abstract

A series of bifunctional cyclopentadienes of the type 1,3-EtOCO-HCp-linker-NH2 were synthesized. In this series, the linker length (distance between the amine functionalities and the cyclopentadiene) has been systematically varied (CH2)n (n = 1–3). The corresponding Re complexes [(η5-C5H3RR′)Re(CO)3] (R = −COOEt, R′ = −linker–NH2) were synthesized and structurally characterized. They exhibit extraordinary stability toward water and air. All bifunctional cyclopentadienes have been labeled with the [99mTc(CO)3]+ moiety. Whereas the reactions with ethylene and propylene linked cyclopentadiene under mild reaction conditions led to the products in high radiochemical purity (>96%) without applying further purification protocols, harsher reaction conditions were required for the synthesis of the methylene-linked cyclopentadiene compound. Masking the amine in the methylene-linked cyclopentadiene by an amide bond bypasses this problem. The very hydrophilic characters of these complexes were assessed by KOW analysis. The reported cyclopentadienes and their complexes offer a robust and versatile platform for (radio)metal incorporation into biologically active lead structures.

Abstract

A series of bifunctional cyclopentadienes of the type 1,3-EtOCO-HCp-linker-NH2 were synthesized. In this series, the linker length (distance between the amine functionalities and the cyclopentadiene) has been systematically varied (CH2)n (n = 1–3). The corresponding Re complexes [(η5-C5H3RR′)Re(CO)3] (R = −COOEt, R′ = −linker–NH2) were synthesized and structurally characterized. They exhibit extraordinary stability toward water and air. All bifunctional cyclopentadienes have been labeled with the [99mTc(CO)3]+ moiety. Whereas the reactions with ethylene and propylene linked cyclopentadiene under mild reaction conditions led to the products in high radiochemical purity (>96%) without applying further purification protocols, harsher reaction conditions were required for the synthesis of the methylene-linked cyclopentadiene compound. Masking the amine in the methylene-linked cyclopentadiene by an amide bond bypasses this problem. The very hydrophilic characters of these complexes were assessed by KOW analysis. The reported cyclopentadienes and their complexes offer a robust and versatile platform for (radio)metal incorporation into biologically active lead structures.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biotechnology
Physical Sciences > Bioengineering
Physical Sciences > Biomedical Engineering
Life Sciences > Pharmacology
Life Sciences > Pharmaceutical Science
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Pharmaceutical Science, Pharmacology, Biomedical Engineering, Bioengineering, Biotechnology
Language:English
Date:21 July 2021
Deposited On:27 Aug 2021 07:24
Last Modified:25 Feb 2024 02:42
Publisher:American Chemical Society (ACS)
ISSN:1043-1802
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.bioconjchem.0c00468
PubMed ID:32997491
Project Information:
  • : FunderSNF
  • : Grant IDIZSZL2_149029
  • : Project Title
  • Content: Accepted Version