Click chemistry for [99mTc(CO)3] labeling of Lys3-bombesin

Ferro-Flores, Guillermina; Rivero, Ignacio A.; Santos-Cuevas, Clara; Sarmiento, Juan I.; Murphy, Consuelo Arteaga de; Ocampo‐García, Blanca; Garcı́a-Becerra, Rocı́o; Ordaz-Rosado, David

doi:10.1016/j.apradiso.2010.06.014

Cited by 13 publications

(11 citation statements)

References 23 publications

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“…[78] The progesterone-triazole derivatives 18 were synthesized and radiolabeled with the [ 99m Tc(CO) 3 A C H T U N G T R E N N U N G (H 2 O) 3 ] + precursor in 95 % radiochemical yield. [79] In vitro studies carried out in MCF7 cells indicated binding to the extent of 30 %.…”

Section: Anticancermentioning

confidence: 99%

“…Ferro-Flores and co-workers synthesized new 99m Tc(CO) 3triazole-Lys 3 -bombesin analogue 17 by click chemistry and found it to have promising characteristics as an effective radiopharmaceutical for the diagnosis of GRP receptor overexpressing tumors. [78] The progesterone-triazole derivatives 18 were synthesized and radiolabeled with the [ 99m Tc(CO) 3 A C H T U N G T R E N N U N G (H 2 O) 3 ] + precursor in 95 % radiochemical yield. [79] In vitro studies carried out in MCF7 cells indicated binding to the extent of 30 %.…”

Section: Anticancermentioning

confidence: 99%

“…The structure-activity relationship of the resulting triazole-linked hydroxamates displayed a cap-group-dependent preference for either five-or six-methylene spacer groups. Chen et al identified compounds (78), that were several folds more potent than SAHA. [143] A subset of these compounds also inhibited the proliferation of DU-145 cells.…”

Section: Miscellaneousmentioning

confidence: 99%

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Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,169

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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Section: Anticancermentioning

confidence: 99%

Section: Anticancermentioning

confidence: 99%

Section: Miscellaneousmentioning

confidence: 99%

See 1 more Smart Citation

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,169

508

View full text Add to dashboard Cite

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“…For example, compounds such as 1 are active against Mycobacterium tuberculosis [7]; other compounds act as anticancer 2 [8], antifungal 3 [9], or antitumor agents 4 [10], Scheme 1. Some biomedical applications have been described, for example, the labelling of biomolecules [11]. In addition, 1,2,3-triazoles have been used in the coupling of modified α -amino acids in oligopeptide synthesis [4, 12–17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

Sarmiento-Sánchez

Ochoa-Terán

Rivero

2014

The Scientific World Journal

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The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters 6 are reported in good yields from an in situ generated α-azidomethyl ketone. Optimum experimental conditions were established for preparation of α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11, all derived from α-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds 6 was assayed by DPPH method. The compound 6c with an IC50 of 75.57 ± 1.74 μg mL−1 was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modified α-amino acids employed in the synthesis.

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“…single amino acid chelate) 7, 8 or containing orthogonal chemical moieties (e.g. azides, alkynes) for chelate generation or attachment 9–11 can be introduced at specific locations within a peptide sequence during solid phase production strategies. Such site specific chelate incorporation is more difficult in larger, recombinantly produced proteins (e.g.…”

Section: Introductionmentioning

confidence: 99%

Novel, Cysteine-Modified Chelation Strategy for the Incorporation of [M^I(CO)₃]⁺ (M = Re, ^99mTc) in an α-MSH Peptide

et al. 2012

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Engineering peptide-based targeting agents with residues for site specific and stable complexation of radionuclides is a highly desirable strategy for producing diagnostic and therapeutic agents for cancer and other diseases. In this report, a model N-S-NPy ligand (3) and a cysteine-derived alpha-melanocyte stimulating hormone (α-MSH) peptide (6) were used as novel demonstrations of a widely applicable chelation strategy for incorporation of the [MI(CO)3]+ (M = Re, 99mTc) core into peptide-based molecules for radiopharmaceutical applications. The structural details of the core ligand-metal complexes as model systems were demonstrated by full chemical characterization of fac-[ReI(CO)3(N,S,NPy-3)]+ (4) and comparative high performance liquid chromatography (HPLC) analysis between 4 and [99mTcI(CO)3(N,S,NPy-3)]+ (4a). The α-MSH analogue bearing the N-S-NPy chelate on a modified cysteine residue (6) was generated and complexed with [MI(CO)3]+ to confirm the chelation strategy’s utility when applied in a peptide-based targeting agent. Characterization of the ReI(CO)3-6 peptide conjugate (7) confirmed the efficient incorporation of the metal center, and the 99mTcI(CO)3-6 analogue (7a) was explored as a potential single photon emission computed tomography (SPECT) compound for imaging the melanocortin 1 receptor (MC1R) in melanoma. Peptide 7a showed excellent radiolabeling yields and in vitro stability during amino acid challenge and serum stability assays. In vitro B16F10 melanoma cell uptake of 7a reached a modest value of 2.3 ± 0.08% of applied activity at 2 h at 37 °C while this uptake was significantly reduced by coincubation with a nonlabeled α-MSH analogue, NAPamide (3.2 µM) (P < 0.05). In vivo SPECT/X-ray computer tomography (SPECT/CT) imaging and biodistribution of 7a were evaluated in a B16F10 melanoma xenografted mouse model. SPECT/CT imaging clearly visualized the tumor at 1 h post injection (p.i.) with high tumor-to-background contrast. Blocking studies with coinjected NAPamide (10 mg per kg of mouse body weight) confirmed the in vivo specificity of 7a for MC1R-positive tumors. Biodistribution results with 7a yielded a moderate tumor uptake of 1.20 ± 0.09 percentage of the injected radioactive dose per gram of tissue (% ID/g) at 1 h p.i. Relatively high uptake of 7a was also seen in the kidneys and liver at 1 h p.i. (6.55 ± 0.36% ID/g and 4.44 ± 0.17% ID/g, respectively), although reduced kidney uptake was seen at 4 h p.i. (3.20 ± 0.48% ID/g). These results demonstrate the utility of the novel [MI(CO)3]+ chelation strategy when applied in a targeting peptide.

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Click chemistry for [99mTc(CO)3] labeling of Lys3-bombesin

Cited by 13 publications

References 23 publications

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

Novel, Cysteine-Modified Chelation Strategy for the Incorporation of [M^I(CO)₃]⁺ (M = Re, ^99mTc) in an α-MSH Peptide

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Click chemistry for [99mTc(CO)3] labeling of Lys3-bombesin

Cited by 13 publications

References 23 publications

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

Novel, Cysteine-Modified Chelation Strategy for the Incorporation of [MI(CO)3]+ (M = Re, 99mTc) in an α-MSH Peptide

Contact Info

Product

Resources

About

Novel, Cysteine-Modified Chelation Strategy for the Incorporation of [M^I(CO)₃]⁺ (M = Re, ^99mTc) in an α-MSH Peptide