A convenient synthesis, chemical characterization and reactivity of [Re(CO)3(H2O)3]Br: the crystal and molecular structure of [Re(CO)3(CH3CN)2Br]

Lazarova, Neva; James, Shelly; Babich, John W.; Zubieta, Jon

doi:10.1016/j.inoche.2004.07.006

Cited by 135 publications

(63 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of the rhenium compounds-fac-[Re(CO) 3 ((bis (6- [38] (40.2 mg, 100 mmol) in methanol (2 mL) was then added and heating at reflux was continued for 2 h. After cooling to room temperature the reaction mixture was filtered. The orange brownish solution was concentrated to a volume of about 5 mL and filtered again.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

et al. 2011

View full text Add to dashboard Cite

Organometallic complexes possess great potential for imaging applications in biology, due to their kinetic stability and often favourable intrinsic properties. In this work we present a new class of Re(I) -tricarbonyl complexes with a substituted bis(phenanthridinylmethyl)amine (bpm) ligand. The complex Re(CO)(3) (R-bpm) could be conveniently prepared by microwave synthesis from [Re(CO)(3)(H(2)O)(3) ]Br and a suitably substituted bis(phenanthridinylmethyl)amine (R-bpm). Complex 5, with R=CH(2)-CO(2)-CH(3) , was characterized by a single-crystal X-ray structure. Complex 6 (R=CH(2)-C(6)H(4)-CO(2)H) was used in solid-phase peptide synthesis (SPPS) to label the neurotensin(8-13) (NT) fragment N-terminally. The complexes show luminescence emission with large Stokes shifts (λ(ex) =350 nm, λ(em) =570 nm). Cellular uptake and intracellular localization studies in several cell lines demonstrate the utility of the new Re(CO)(3) (R-bpm) complexes for fluorescence imaging and reveal significant differences between the simple methyl ester 5 and the NT bioconjugate 7.

show abstract

Section: Methodsmentioning

confidence: 99%

“…[38] The bisphenanthridinylmethyl (bpm) rhenium(I) tricarbonyl complexes 5 and 6 were synthesised by two different methods (Scheme 2). In the first method, the bpm ligand was heated at reflux together with [Re(CO) 3 3 ]Br in a microwave reactor in methanol for 10 min at 110 8C.…”

Section: Introductionmentioning

confidence: 99%

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

et al. 2011

View full text Add to dashboard Cite

show abstract

“…[38] For in vitro cell studies, all manipulations were performed in a Labconco Purifier I laminar flow hood that had been disinfected with 70 % ethanol and irradiated with UV light. CHO cells were obtained from the American Type Culture Collection (ATCC).…”

Section: A C H T U N G T R E N N U N G (H 2 O) 3 ]mentioning

confidence: 99%

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells

et al. 2008

Self Cite

View full text Add to dashboard Cite

The synthesis, characterization, in vitro imaging, and cytotoxic properties of a new folate conjugate of rhenium(I) are reported. The conjugate [FA-PEG-BQAV-Re(CO)3]+ (gamma-4) was screened against an adriamycin- and cisplatin-resistant human ovarian cancer cell line (A2780/AD) that overexpresses the folate receptor (FR). Compound gamma-4 was internalized by a folate-receptor-mediated endocytotic pathway, which results in internal accumulation of gamma-4. This was contrasted with a FR-negative Chinese hamster ovary cell line in which no internalization of gamma-4 was observed. gamma-4 was found to be cytotoxic with IC(50) values of 189 and 78 microM at 6 and 24 h, respectively, toward the FR-positive cell line. This is in contrast to the IC(50) value of 502 microM at 6 h and 84 microM at 24 h for cisplatin in the same cell line, with a significantly greater toxicity at the earlier time point. The cytotoxicity of gamma-4 as explained by interactions that occur between the rhenium(I) complex moiety and DNA is described.

show abstract

“…All ligands of the type D(C x )lisinopril (where x is the total number of carbons in the tether including the methylene and carbonyl carbons) and their intermediates were previously reported and synthesized according to published literature procedures (11,15,16). The starting material, [Re(CO) 3 (H 2 O) 3 ]Br, was synthesized according to previously described methods (17). Elemental analysis was performed by Desert Analytics, electrospray mass spectrometry by HT Laboratories, and 1 H nuclear magnetic resonance (NMR) spectroscopy by Custom NMR Services.…”

Section: Generalmentioning

confidence: 99%

“…Commercially available e-amino acids were converted to the corresponding di(2-pyridylmethylamino)alkanoic acids (11,15,16) via reductive amination under standard conditions in good yields (16). Activation of the free acid under standard peptidecoupling conditions followed by addition of lisinopril afforded the desired free ligand conjugates (8,17,18) in moderate yields. The free ligands were directly radiolabeled with 99m Tc or complexed with rhenium as described later.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Evaluation of a Series of ^99mTc(CO)₃⁺ Lisinopril Complexes for In Vivo Imaging of Angiotensin-Converting Enzyme Expression

Femia¹,

Maresca²,

Hillier³

et al. 2008

J Nucl Med

View full text Add to dashboard Cite

A convenient synthesis, chemical characterization and reactivity of [Re(CO)3(H2O)3]Br: the crystal and molecular structure of [Re(CO)3(CH3CN)2Br]

Cited by 135 publications

References 15 publications

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells

Synthesis and Evaluation of a Series of ^99mTc(CO)₃⁺ Lisinopril Complexes for In Vivo Imaging of Angiotensin-Converting Enzyme Expression

Contact Info

Product

Resources

About

A convenient synthesis, chemical characterization and reactivity of [Re(CO)3(H2O)3]Br: the crystal and molecular structure of [Re(CO)3(CH3CN)2Br]

Cited by 135 publications

References 15 publications

A Novel Organometallic ReI Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

A Novel Organometallic ReI Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of ReI Conjugates in FR‐Overexpressing Cancer Cells

Synthesis and Evaluation of a Series of 99mTc(CO)3+ Lisinopril Complexes for In Vivo Imaging of Angiotensin-Converting Enzyme Expression

Contact Info

Product

Resources

About

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

A Novel Organometallic Re^I Complex with Favourable Properties for Bioimaging and Applicability in Solid‐Phase Peptide Synthesis

Targeting the Folate Receptor (FR): Imaging and Cytotoxicity of Re^I Conjugates in FR‐Overexpressing Cancer Cells

Synthesis and Evaluation of a Series of ^99mTc(CO)₃⁺ Lisinopril Complexes for In Vivo Imaging of Angiotensin-Converting Enzyme Expression