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Title: DL-(carboxyl-/sup 11/C)tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations

Abstract

In animal studies, DL-(carboxyl-/sup 14/C)tryptophan (DL-Try(C-14)) showed a high specificity for the pancreas, which suggested the potential of DL-(carboxyl-/sup 11/C)tryptophan (DL-Try(C-11)) for clinical pancreatic imaging. The blood clearance and tissue uptake of the amino acid were very rapid, and no carrier effect was observed through a dose of 5 mg/kg. None of three transplanted hamster pancreatic adenocarcinomas that we studied showed a selective uptake of DL-Try(C-14) by the tumor, and none of the three enzymatic regimens investigated gave significant enhancement of the pancreatic specificity. Commercial L-Try(C-14) gave slightly better pancreatic specificity than the analogous racemic compound but without enough improvement to warrant attempts at optical resolution. DL-Try(C-11) was synthesized in amounts up to 325 mCi using a rapid, high-temperature, high-pressure modification of the Buecherer-Strecker amino acid synthesis. Yields ranged from 30 to 60%, and a total of 40 min was required for synthesis and chromatographic purification. DL-Try(C-11) thus appears to have significant potential as a clinical pancreas-imaging agent, particularly when used in conjunction with positron computerized transaxial tomography.

Authors:
; ; ; ;
Publication Date:
Research Org.:
Oak Ridge Associated Universities, TN
OSTI Identifier:
5998799
DOE Contract Number:  
W-7405-ENG-26
Resource Type:
Journal Article
Journal Name:
J. Nucl. Med.; (United States)
Additional Journal Information:
Journal Volume: 20:8
Country of Publication:
United States
Language:
English
Subject:
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.; 62 RADIOLOGY AND NUCLEAR MEDICINE; 38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; CARBON 11; ECAT SCANNING; RADIOPHARMACEUTICALS; SCINTISCANNING; CARBOXYLIC ACID ESTERS; DOGS; RADIONUCLIDE KINETICS; PANCREAS; BIOLOGICAL LOCALIZATION; CHEMICAL PREPARATION; TISSUE DISTRIBUTION; RATS; TRYPTOPHAN; BLOOD-PLASMA CLEARANCE; EXPERIMENTAL DATA; FEASIBILITY STUDIES; ISOLATED VALUES; AMINO ACIDS; ANIMALS; AZOLES; BETA DECAY RADIOISOTOPES; BETA-PLUS DECAY RADIOISOTOPES; BODY; CARBON ISOTOPES; CARBOXYLIC ACIDS; CAT SCANNING; CLEARANCE; COUNTING TECHNIQUES; DATA; DATA FORMS; DIAGNOSTIC TECHNIQUES; DIGESTIVE SYSTEM; DISTRIBUTION; DRUGS; ENDOCRINE GLANDS; ESTERS; EVEN-ODD NUCLEI; GLANDS; HETEROCYCLIC ACIDS; HETEROCYCLIC COMPOUNDS; INDOLES; INFORMATION; ISOTOPES; LABELLED COMPOUNDS; LIGHT NUCLEI; MAMMALS; MINUTES LIVING RADIOISOTOPES; NUCLEI; NUMERICAL DATA; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANS; PHOTON EMISSION SCANNING; PHOTON TRANSMISSION SCANNING; PYRROLES; RADIOACTIVE MATERIALS; RADIOISOTOPE SCANNING; RADIOISOTOPES; RODENTS; SYNTHESIS; TOMOGRAPHY; VERTEBRATES; 560172* - Radiation Effects- Nuclide Kinetics & Toxicology- Animals- (-1987); 550601 - Medicine- Unsealed Radionuclides in Diagnostics; 400702 - Radiochemistry & Nuclear Chemistry- Properties of Radioactive Materials

Citation Formats

Washburn, L C, Sun, T T, Byrd, B L, Hayes, R L, and Butler, T A. DL-(carboxyl-/sup 11/C)tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations. United States: N. p., 1979. Web.
Washburn, L C, Sun, T T, Byrd, B L, Hayes, R L, & Butler, T A. DL-(carboxyl-/sup 11/C)tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations. United States.
Washburn, L C, Sun, T T, Byrd, B L, Hayes, R L, and Butler, T A. 1979. "DL-(carboxyl-/sup 11/C)tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations". United States.
@article{osti_5998799,
title = {DL-(carboxyl-/sup 11/C)tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations},
author = {Washburn, L C and Sun, T T and Byrd, B L and Hayes, R L and Butler, T A},
abstractNote = {In animal studies, DL-(carboxyl-/sup 14/C)tryptophan (DL-Try(C-14)) showed a high specificity for the pancreas, which suggested the potential of DL-(carboxyl-/sup 11/C)tryptophan (DL-Try(C-11)) for clinical pancreatic imaging. The blood clearance and tissue uptake of the amino acid were very rapid, and no carrier effect was observed through a dose of 5 mg/kg. None of three transplanted hamster pancreatic adenocarcinomas that we studied showed a selective uptake of DL-Try(C-14) by the tumor, and none of the three enzymatic regimens investigated gave significant enhancement of the pancreatic specificity. Commercial L-Try(C-14) gave slightly better pancreatic specificity than the analogous racemic compound but without enough improvement to warrant attempts at optical resolution. DL-Try(C-11) was synthesized in amounts up to 325 mCi using a rapid, high-temperature, high-pressure modification of the Buecherer-Strecker amino acid synthesis. Yields ranged from 30 to 60%, and a total of 40 min was required for synthesis and chromatographic purification. DL-Try(C-11) thus appears to have significant potential as a clinical pancreas-imaging agent, particularly when used in conjunction with positron computerized transaxial tomography.},
doi = {},
url = {https://www.osti.gov/biblio/5998799}, journal = {J. Nucl. Med.; (United States)},
number = ,
volume = 20:8,
place = {United States},
year = {Wed Aug 01 00:00:00 EDT 1979},
month = {Wed Aug 01 00:00:00 EDT 1979}
}