Syntheses of carbon-11 labelled ornithine and lysine. Preliminary accumulation studies in rats with Walker 256 carcinosarcoma

Bolster, Jm; Vaalburg, W; Dijk, Theo H. van; Zijlstra, J.B.; Paans, Anne M. J.; Wynberg, Hans; Woldring, Mg

doi:10.1016/0020-708x(85)90082-1

Cited by 16 publications

(15 citation statements)

References 15 publications

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“…The authors attempted to separate the enantiomers by HPLC using both chiral stationary phases and chiral mobile phases without success and suggested an enzymatic resolution method using an immobilized D-amino acid oxydase/ catalase. 273 To produce [6-11 C]lysine, the anion of (S)-Boc-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one was treated with lithium 2,2,6,6-tetramethylpiperidide to initiate deprotonation of the α-carbon, followed by a 11 C alkylation with 4-[ 11 C]iodobutyronitrile, and subsequent reduction and hydrolysis to furnish the D,L-[6-11 C]lysine. However, these were only preliminary findings, and no details about the RCY, RCP, or ee were provided.…”

Section: Dl-[1-mentioning

confidence: 99%

“…However, no attempts have been made to resolve the D,L-[1- 11 Clproline in its enantiomers. 273 4.17.2. Preclinical Studies.…”

Section: Preclinical Studies Dl-[1-mentioning

confidence: 99%

“…Labeling of lysine has been performed in positions 1 - or 6 - from two different groups, and no modifications or other methods have been published (Figure ). , …”

Section: Amino Acidsmentioning

confidence: 99%

“…The preparation was achieved by carboxylation of α -lithiopyrrolidyl- N - tert -butyl-formamidine followed by regeneration of the amine functionality with a RCY of 12-18% and RCP >95% within 45 min. However, no attempts have been made to resolve the d , l -[ 1 - 11 Clproline in its enantiomers …”

Section: Amino Acidsmentioning

confidence: 99%

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Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

et al. 2022

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The presence of positron emission tomography (PET) centers at most major hospitals worldwide, along with the improvement of PET scanner sensitivity and the introduction of total body PET systems, has increased the interest in the PET tracer development using the short-lived radionuclides carbon-11. In the last few decades, methodological improvements and fully automated modules have allowed the development of carbon-11 tracers for clinical use. Radiolabeling natural compounds with carbon-11 by substituting one of the backbone carbons with the radionuclide has provided important information on the biochemistry of the authentic compounds and increased the understanding of their in vivo behavior in healthy and diseased states. The number of endogenous and natural compounds essential for human life is staggering, ranging from simple alcohols to vitamins and peptides. This review collates all the carbon-11 radiolabeled endogenous and natural exogenous compounds synthesised to date, including essential information on their radiochemistry methodologies and preclinical and clinical studies in healthy subjects.

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Section: Dl-[1-mentioning

confidence: 99%

“…However, no attempts have been made to resolve the D,L-[1- 11 Clproline in its enantiomers. 273 4.17.2. Preclinical Studies.…”

Section: Preclinical Studies Dl-[1-mentioning

confidence: 99%

“…Labeling of lysine has been performed in positions 1 - or 6 - from two different groups, and no modifications or other methods have been published (Figure ). , …”

Section: Amino Acidsmentioning

confidence: 99%

Section: Amino Acidsmentioning

confidence: 99%

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Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

et al. 2022

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“…Using this route, as described in Fig. 3a, a vast number of racemic [ 11 C]AAs have been described in literature, namely phenylalanine [26], ornithine and lysine [38], tyrosine [28,30], proline [39] and phenylglycine [26], and achiral glycine [25,26]. The [1][2][3][4][5][6][7][8][9][10][11] C]proline has been reported in 12-18 % RCY with a RCP of 9 95 % in total synthesis time of 45 min [39].…”

Section: Carbon-11 Amino Acid Labelingmentioning

confidence: 99%

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

et al. 2018

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Radiolabeled amino acids, their derivatives and peptides have a broad scope of application and can be used as receptor ligands, as well as enzyme substrates for many different diseases as radiopharmaceutical tracers. Over the past few decades, the application of molecular imaging techniques such as positron emission tomography (PET) has gained considerable importance and significance in diagnosis in today's advanced health care. Next to that, the availability of cyclotrons and state-of-the-art radiochemistry facilities has progressed the production of imaging agents enabling the preparation of many versatile PET radiotracers. Due to many favorable characteristics of radiolabeled amino acids and peptides, they can be used for tumor staging and monitoring the progress of therapy success, while aromatic amino acids can be employed as PET tracer to study neurological disorders. This review provides a comprehensive overview of radiosynthetic and enzymatic approaches towards carbon-11 amino acids, their analogues and peptides, with focus on stereoselective reactions, and reflects upon their clinical application.

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Synthesis of racemic [3‐¹¹C]‐labelled alanine, 2‐aminobutyric acid, norvaline, norleucine, leucine and phenylalanine and preparation of L‐[3‐¹¹C]alanine and L‐[3‐¹¹C]phenylalanine

Antoni

Långström

1987

Labelled Comp Radiopharmac

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The syntheses of racemic [3‐11C]‐labelled alanine, 2‐amino‐butyric acid, norvaline, norleucine, leucine and phenyl‐alanine are reported. The reaction were performed by a phase‐transfer alkylation reaction on N‐(diphenylmethylene)‐glycine tert‐butyl ester with the appropriate 11C‐alkyl iodides followed by acidic hydrolysis and the labelled amino acids were obtained in 10‐55 % radiochemical yield. L‐[3‐11C]‐Alanine and L‐[3‐11C]phenylalanine were obtained in 99 % enantiomeric excess after treatment of the corresponding racemic mixture by D‐amino acid oxidase immobilized on glutaral‐dehyde‐activated glass beads. In a typical run starting with 120 mCi [11C]carbon dioxide, 25 mCi [1‐11C]benzyl iodide was prepared and used to give 6 mCi of DL‐[3‐11C]phenylalanine within 50 minutes. Following treatment with D‐amino acid oxidase, 0.3 mCi of L‐[3‐11C]phenylalanine was obtained after a total synthesis time of about 100 minutes.

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Syntheses of carbon-11 labelled ornithine and lysine. Preliminary accumulation studies in rats with Walker 256 carcinosarcoma

Cited by 16 publications

References 15 publications

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

Synthesis of racemic [3‐¹¹C]‐labelled alanine, 2‐aminobutyric acid, norvaline, norleucine, leucine and phenylalanine and preparation of L‐[3‐¹¹C]alanine and L‐[3‐¹¹C]phenylalanine

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Syntheses of carbon-11 labelled ornithine and lysine. Preliminary accumulation studies in rats with Walker 256 carcinosarcoma

Cited by 16 publications

References 15 publications

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

Synthesis of racemic [3‐11C]‐labelled alanine, 2‐aminobutyric acid, norvaline, norleucine, leucine and phenylalanine and preparation of L‐[3‐11C]alanine and L‐[3‐11C]phenylalanine

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Synthesis of racemic [3‐¹¹C]‐labelled alanine, 2‐aminobutyric acid, norvaline, norleucine, leucine and phenylalanine and preparation of L‐[3‐¹¹C]alanine and L‐[3‐¹¹C]phenylalanine