[111In-DTPA-D-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: synthesis, radiolabeling and in vitro validation

Bakker, Willem H.; Albert, Rainer; Berthou, Christian; Breeman, W. A. P.; Hofland, Leo J.; Marbach, Peter; Pless, J.; Pralet, Dominique; Stolz, Barbara; Koper, Jan W.; Lamberts, Steven W. J.; Visser, Theo J.; Krenning, Eric P.

doi:10.1016/0024-3205(91)90052-d

Cited by 313 publications

(168 citation statements)

References 12 publications

Supporting

Mentioning

161

Contrasting

Unclassified

Order By: Relevance

“…However, similar strategies have been used for years in the field of positron emission tomography (PET), which often involves incorporation of a radioactive nucleus into a ligand of interest shortly before administration to a patient. For example, biological peptides of interest bearing artificial amino acid side-chains as chelating groups can be ''tagged'' with positron-emitting isotopes such as technecium-99 and delivered to a patient (23,24). These labeled tracers can then be assessed in vivo, using a gamma camera.…”

Section: Discussionmentioning

confidence: 99%

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

Wilson

Hurd²,

Keshari

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

In this manuscript, the remarkable NMR signal enhancement that can be provided by dynamic nuclear polarization (DNP) was combined with the reactivity of acetic anhydride with amines to perform rapid, high SNR analyses of amino acid mixtures and to hyperpolarize new biomolecules of interest. [1,1-13 C] acetic anhydride is an excellent substrate for DNP hyperpolarization because it can be well polarized in only 30 min and has a relatively long T1 relaxation time (33.9 s at 11.7 T and 37°C). The secondary hyperpolarization approach developed in this project takes advantage of the preferential reaction of acetic anhydride with amine nucleophiles, which occurs much more rapidly than hydrolysis to produce hyperpolarized N-acetyl adducts. This new approach was used to reproducibly and near-quantitatively (mean yield ؊ 89.8%) resolve a mixture of amino acids Gly, Ser, Val, Leu, and Ala in a single acquisition (3 s) with a signal enhancement of up to 1,400-fold as compared with thermal equilibrium. Secondary hyperpolarization was performed for several small peptides and N-acetylcysteine, a drug administered intravenously to treat acetaminophen overdose. Although, in general the T1 of the N-acetyl adducts decreased with increasing molecular weight of the biomolecules, the T1 values were still on the order of 10 s, and the correlation of T1 with molecular weight was not exact suggesting the potential of secondarily polarizing relatively large biomolecules. This study demonstrates the feasibility of using prepolarized [1,1-13 C] acetic anhydride and rapid chemical reactions to provide high SNR NMR spectra of amino acid derivatives and other biomolecules.acetylation ͉ metabolism ͉ peptides ͉ spectroscopy

show abstract

Section: Discussionmentioning

confidence: 99%

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

Wilson

Hurd²,

Keshari

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

show abstract

“…In-DTPAOctreotide, D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr[ol]), was successfully used to visualize somatostatin receptor positive tumors by gamma camera scintigraphy in the early 1990s [48][49][50] . Normal physiological uptake is seen in the thyroid, spleen, liver and pituitary due to receptor binding of the peptides, while tracer uptake in the kidneys is predominantly secondary to reabsorption of filtered peptides, and bowel uptake is presumably secondary to hepatobiliary clearance (Figures 6 and 7).…”

mentioning

confidence: 99%

Imaging of gastroenteropancreatic neuroendocrine tumors

Tan

Tan²

2011

WJCO

View full text Add to dashboard Cite

Imaging of gastroenteropancreatic neuroendocrine tumors can be broadly divided into anatomic and functional techniques. Anatomic imaging determines the local extent of the primary lesion, providing crucial information required for surgical planning. Functional imaging, not only determines the extent of metastatic disease spread, but also provides important information with regard to the biologic behavior of the tumor, allowing clinicians to decide on the most appropriate forms of treatment. We review the current literature on this subject, with emphasis on the strengths of each imaging modality.

show abstract

“…Several ␣-MSH analogs have been examined for their abilities to target melanoma. [13][14][15][16] In our lab, a novel class of metal-cyclized ␣-MSH analogs have been developed that center on the CCMSH ([Cys 3,4,10 Tc-CCMSH analogs, cyclized through site-specific coordination of 99m TcO, were the first to be examined for their melanoma targeting properties. Peptide cyclization with 99m Tc made the molecules resistant to chemical and proteolytic degradation in vivo while retaining high bioactivities.…”

mentioning

confidence: 99%

In vivo evaluation of ¹⁸⁸Re‐labeled alpha‐melanocyte stimulating hormone peptide analogs for melanoma therapy

Miao¹,

Owen²,

Whitener³

et al. 2002

Intl Journal of Cancer

View full text Add to dashboard Cite

The purpose of our study was to optimize melanoma tumor uptake of 188 Re-CCMSH and reduce its nonspecific kidney retention. Nephrotoxicity is often a serious problem associated with targeted radiotherapy, therefore, increasing the tumor/kidney uptake ratio of 188 Re-CCMSH is crucial for optimizing its therapeutic efficacy. Structural modification of the peptide and amino acid co-infusion were investigated as strategies to improve the tumor/kidney uptake ratio of 188 Re-CCMSH. The substitution of Lys 11 with Arg 11 was examined to determine if removal of lysine from the peptide would improve kidney clearance without sacrificing tumor uptake.

show abstract

[111In-DTPA-D-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: synthesis, radiolabeling and in vitro validation

Cited by 313 publications

References 12 publications

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

Imaging of gastroenteropancreatic neuroendocrine tumors

In vivo evaluation of ¹⁸⁸Re‐labeled alpha‐melanocyte stimulating hormone peptide analogs for melanoma therapy

Contact Info

Product

Resources

About

[111In-DTPA-D-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: synthesis, radiolabeling and in vitro validation

Cited by 313 publications

References 12 publications

Generation of hyperpolarized substrates by secondary labeling with [1,1- 13 C] acetic anhydride

Generation of hyperpolarized substrates by secondary labeling with [1,1- 13 C] acetic anhydride

Imaging of gastroenteropancreatic neuroendocrine tumors

In vivo evaluation of 188Re‐labeled alpha‐melanocyte stimulating hormone peptide analogs for melanoma therapy

Contact Info

Product

Resources

About

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

Generation of hyperpolarized substrates by secondary labeling with [1,1- ¹³ C] acetic anhydride

In vivo evaluation of ¹⁸⁸Re‐labeled alpha‐melanocyte stimulating hormone peptide analogs for melanoma therapy