Bridging the gap between in vitro and in vivo imaging: Isostructural Re and 99mTc complexes for correlating fluorescence and radioimaging studies

Karin A. Stephenson, Sangeeta Ray, Travis Besanger, Oyebola O. Sogbein, Murali K. Levadala, Nicole McFarlane, Jennifer A. Lemon, Douglas R. Boreham, Kevin P. Maresca, John D. Brennan, John W. Babich, Jon Zubieta, John F. Valliant

Research output: Contribution to journalArticle

Abstract

A bifunctional ligand that is capable of forming Re and 99mTc complexes as complementary fluorescent and radioactive probes was developed. The tridentate bis(quinoline) amine ligand, which is referred to as the SAACQ system, was prepared in a single step from Fmoc protected lysine in high yield. Reaction of the SAACQ ligand with [Re(CO)3Br3]2- resulted in the formation of the SAACQ-(Re(CO)3)+complex which exhibits favorable fluorescence properties including a long lifetime and a large Stoke's shift. Because the SAACQ ligand is derived from an amino acid, it can readily be linked to or incorporated within peptides as a means of targeting the probe to specific receptors. To demonstrate this feature, the SAACQ ligand and the SAACQ-Re complex were incorporated into fMLFG, a peptide that binds to the formyl peptide receptor (FPR). Uptake of the fMLF[(SAACQ-Re(CO)3)+]G conjugate into human leukocytes in vitro was visualized by fluorescence microscopy, and the observed distribution of the peptide was similar to that of a well-established fluorescent FPR probe. The corresponding Tc complex, fMLF[(SAACQ-99mTc(CO)3)+]G, was prepared in excellent yield from [99mTc(CO)3(OH2)3]+, which affords the opportunity to correlate the results of the microscopy experiments with in vivo radioimaging studies because the probes are isostructural.

Original languageEnglish (US)
Pages (from-to)8598-8599
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number28
DOIs
StatePublished - Jul 21 2004
Externally publishedYes

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Carbon Monoxide
Peptides
Fluorescence
Ligands
Imaging techniques
Formyl Peptide Receptor
Fluorescence microscopy
Fluorescent Dyes
Fluorescence Microscopy
Lysine
Amines
Amino acids
Microscopy
Microscopic examination
Leukocytes
In Vitro Techniques
Amino Acids
Experiments

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bridging the gap between in vitro and in vivo imaging : Isostructural Re and 99mTc complexes for correlating fluorescence and radioimaging studies. / Stephenson, Karin A.; Ray, Sangeeta; Besanger, Travis; Sogbein, Oyebola O.; Levadala, Murali K.; McFarlane, Nicole; Lemon, Jennifer A.; Boreham, Douglas R.; Maresca, Kevin P.; Brennan, John D.; Babich, John W.; Zubieta, Jon; Valliant, John F.

In: Journal of the American Chemical Society, Vol. 126, No. 28, 21.07.2004, p. 8598-8599.

Research output: Contribution to journalArticle

Stephenson, KA, Ray, S, Besanger, T, Sogbein, OO, Levadala, MK, McFarlane, N, Lemon, JA, Boreham, DR, Maresca, KP, Brennan, JD, Babich, JW, Zubieta, J & Valliant, JF 2004, 'Bridging the gap between in vitro and in vivo imaging: Isostructural Re and 99mTc complexes for correlating fluorescence and radioimaging studies', Journal of the American Chemical Society, vol. 126, no. 28, pp. 8598-8599. https://doi.org/10.1021/ja047751b
Stephenson, Karin A. ; Ray, Sangeeta ; Besanger, Travis ; Sogbein, Oyebola O. ; Levadala, Murali K. ; McFarlane, Nicole ; Lemon, Jennifer A. ; Boreham, Douglas R. ; Maresca, Kevin P. ; Brennan, John D. ; Babich, John W. ; Zubieta, Jon ; Valliant, John F. / Bridging the gap between in vitro and in vivo imaging : Isostructural Re and 99mTc complexes for correlating fluorescence and radioimaging studies. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 28. pp. 8598-8599.
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abstract = "A bifunctional ligand that is capable of forming Re and 99mTc complexes as complementary fluorescent and radioactive probes was developed. The tridentate bis(quinoline) amine ligand, which is referred to as the SAACQ system, was prepared in a single step from Fmoc protected lysine in high yield. Reaction of the SAACQ ligand with [Re(CO)3Br3]2- resulted in the formation of the SAACQ-(Re(CO)3)+complex which exhibits favorable fluorescence properties including a long lifetime and a large Stoke's shift. Because the SAACQ ligand is derived from an amino acid, it can readily be linked to or incorporated within peptides as a means of targeting the probe to specific receptors. To demonstrate this feature, the SAACQ ligand and the SAACQ-Re complex were incorporated into fMLFG, a peptide that binds to the formyl peptide receptor (FPR). Uptake of the fMLF[(SAACQ-Re(CO)3)+]G conjugate into human leukocytes in vitro was visualized by fluorescence microscopy, and the observed distribution of the peptide was similar to that of a well-established fluorescent FPR probe. The corresponding Tc complex, fMLF[(SAACQ-99mTc(CO)3)+]G, was prepared in excellent yield from [99mTc(CO)3(OH2)3]+, which affords the opportunity to correlate the results of the microscopy experiments with in vivo radioimaging studies because the probes are isostructural.",
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T2 - Isostructural Re and 99mTc complexes for correlating fluorescence and radioimaging studies

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AU - Ray, Sangeeta

AU - Besanger, Travis

AU - Sogbein, Oyebola O.

AU - Levadala, Murali K.

AU - McFarlane, Nicole

AU - Lemon, Jennifer A.

AU - Boreham, Douglas R.

AU - Maresca, Kevin P.

AU - Brennan, John D.

AU - Babich, John W.

AU - Zubieta, Jon

AU - Valliant, John F.

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