Solid‐Phase Synthesis of a Cyclic NGR‐Functionalized Gd<sup>III</sup>DTPA Complex

Langereis, Sander; Dirksen, Anouk; Waal, Bfm Bas de; Genderen, Mhp Marcel van; Lussanet, Qg Quido de; Hackeng, Tm Tilman; Meijer, E. W.

doi:10.1002/ejoc.200500045

Cited by 8 publications

(6 citation statements)

References 28 publications

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“…Rev., 2011, 40, 3019-3049 3025 a cyclic NGR peptide. 34 Furthermore, 5 was coupled with 4-maleimidobutyric acid 120 and with 3-maleimidobenzoic acid 121 obtaining BFCAs 46 and 47 which are able to conjugate thiol groups (Fig. 10).…”

Section: Dtpa (Diethylenetriaminopentaacetic Acid)mentioning

confidence: 99%

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The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

et al. 2011

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Bifunctional chelating agents (BFCAs) are molecules which contain two different moieties: a strong metal chelating unit and a reactive functional group. The latter is directed to react with amines, thiols, alcohols or other reactive molecules to form stable covalent bonds while the chelating moiety is able to strongly coordinate a metal ion. In this way, it is possible to label a molecule of interest (e.g. an antibody or a peptide) with a metal or a radioactive metal ion. Of all the ligands reported so far, those based on a polyamino polycarboxylic structure are most efficient and are widely employed for the chelation of metal ions. The resulting metal complexes have found a broad range of applications in chemistry, biology and medicine. Diagnostic imaging (MRI, SPECT, PET), molecular imaging, tumour therapy and luminescent materials are only a few examples. The present critical review gives an overview of the syntheses and most important applications of polyamino polycarboxylic BFCAs (334 references).

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Section: Dtpa (Diethylenetriaminopentaacetic Acid)mentioning

confidence: 99%

“…2, path c), but are less common. 34,35 Maleimide (Fig. 2, path d) is another reactive group which has been extensively used because it can easily and specifically react with thiols under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

et al. 2011

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“…14 Langereis and co-workers reported the synthesis of a Gd(III)-DTPA-functionalized dendritic contrast agent modified with a cyclic NGR sequence to encourage preferential binding to tumor vasculature. 15 Multimodal molecular imaging agents are desirable because of the synergy generated from overlapping the strengths of each individual modality thereby compensating for individual inherent limitations. Because of their numerous available conjugation sites, dendrimers are excellent platforms combining MRI, optical, PET, CT and γ-scintigraphic imaging capabilities into a single macromolecular entity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of Integrin α_vβ₃-Targeted PAMAM Dendrimers

et al. 2008

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Ligand size and valency strongly influence the receptor uptake and clearance of tumor angiogenesis imaging agents. The structures of successful imaging agents exhibit a high degree of variability, encompassing small mono-valent arginine-glycine-aspartic acid (RGD)-containing peptides, multivalent RGD-oligomers, and a monoclonal antibody against integrin alpha-v-beta-3 (α v β 3 ). We have pursued a nano-scale approach to imaging of angiogenesis using rationally designed polyamidoamine (PAMAM) dendrimers covalently adorned with RGD-cyclopeptides. An orthogonal oxime-ligation strategy was applied to chemoselectively effect conjugation of the PAMAM dendrimers with RGD-cyclopeptides for targeting α v β 3 . Fluorescent dyes for optical imaging and chelates for gadolinium-based magnetic resonance (MR) imaging were subsequently appended to create robust multimodal macromolecular imaging agents. Fluorescence microscopy revealed selective binding of the resulting RGD peptide-bearing dendrimer with empty chelates to α v β 3 -expressing cells, but somewhat reduced selectivity was observed following Gd(III) complexation. The expected incomplete saturation of chelates with Gd(III) ions permitted radiometal complexation, and an in vivo tissue distribution of the resulting agent in M21 melanoma tumorbearing mice showed mostly renal and reticuloendothelial accumulation, with the tumor:blood ratio peaking (3.30 ± .03) at 2 hr post-injection.

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“…An alternative strategy for developing NGR-functionalised Gd-DTPA-type conjugates has also been reported. 88 The strategy involved the assembly of a small peptide sequence, including target specific NGR on a MBHA resin using SPS. Using both Boc and Fmoc chemistry, selective acylation of the oligopeptide terminal was performed, followed by deprotection of a lysine side chain.…”

Section: Intracellular Casmentioning

confidence: 99%

Solid phase synthesis in the development of magnetic resonance imaging probes

Connah

Angelovski

2020

Org. Chem. Front.

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Solid‐Phase Synthesis of a Cyclic NGR‐Functionalized Gd^IIIDTPA Complex

Abstract: A convenient methodology has been developed for the solidphase synthesis of a cyclic NGR-functionalized Gd III DTPA complex employing an isocyanate-functionalized DTPA pentaester. This methodology is an alternative strategy for

Cited by 8 publications

References 28 publications

The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

Synthesis, Characterization, and Biological Evaluation of Integrin α_vβ₃-Targeted PAMAM Dendrimers

Solid phase synthesis in the development of magnetic resonance imaging probes

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Solid‐Phase Synthesis of a Cyclic NGR‐Functionalized GdIIIDTPA Complex

Abstract: A convenient methodology has been developed for the solidphase synthesis of a cyclic NGR-functionalized Gd III DTPA complex employing an isocyanate-functionalized DTPA pentaester. This methodology is an alternative strategy for

Cited by 8 publications

References 28 publications

The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

The synthesis and application of polyamino polycarboxylic bifunctional chelating agents

Synthesis, Characterization, and Biological Evaluation of Integrin αvβ3-Targeted PAMAM Dendrimers

Solid phase synthesis in the development of magnetic resonance imaging probes

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Product

Resources

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Solid‐Phase Synthesis of a Cyclic NGR‐Functionalized Gd^IIIDTPA Complex

Synthesis, Characterization, and Biological Evaluation of Integrin α_vβ₃-Targeted PAMAM Dendrimers