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Zelenka, K; Borsig, L; Alberto, R (2011). Metal complex mediated conjugation of peptides to nucleus targeting acridine orange: a modular concept for dual-modality imaging agents. Bioconjugate Chemistry, 22(5):958-967.

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Abstract

To target the nucleus of specific cells, trifunctional radiopharmaceuticals are required. We have synthesized acridine orange derivatives which comprise an imidazole-2-carbaldehyde function for coordination to the Re(CO)(3)](+) or (99)mTc(CO)(3)](+) core. Upon coordination, this aldehyde is activated and rapidly forms imines with amines from biological molecules. This metal-mediated imine formation allows for the conjugation of a nuclear targeting portion with a specific cell receptor binding function directly on the metal. With this concept, we have conjugated the acridine orange part to a bombesin peptide directly on the (99m)Tc core and in one step. In addition, a linker containing an integrated disulfide has been coupled to bombesin. LC/MS study showed that the disulfide was reductively cleaved with a 60 min half-life time. This concept enables the combination of a nucleus targeting agent with a specific cell receptor molecule directly on the metal without the need of separate conjugation prior to labeling, thus, a modular approach. High uptake of the BBN conjugate into PC-3 cells was detected by fluorescence microscopy, whereas uptake into B16BL6 cells was negligible.

Citations

17 citations in Web of Science®
20 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
DDC:540 Chemistry
Date:May 2011
Deposited On:12 Mar 2012 16:28
Last Modified:27 Nov 2013 23:14
Publisher:American Chemical Society
ISSN:1043-1802
Publisher DOI:10.1021/bc2000269
Other Identification Number:ISI:000290691600014

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