Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography
The ( R )- and ( S )-enantiomers of 2-amino-3-[1-(2-[ 18 F]fluoroethyl)-1 H -[1,2,3]triazol-4-yl]propanoic acid (4) were synthesized and evaluated in the rat 9L gliosarcoma brain tumor model using cell uptake assays, biodistribution studies, and micro-positron emission tomography (microPET). The ( R...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
SAGE Publishing
2010-11-01
|
| Series: | Molecular Imaging |
| Online Access: | https://doi.org/10.2310/7290.2010.00025 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1841563154196201472 |
|---|---|
| author | Jonathan McConathy Dong Zhou Stephany E. Shockley Lynne A. Jones Elizabeth A. Griffin Hsiaoju Lee Susan J. Adams Robert H. Mach |
| author_facet | Jonathan McConathy Dong Zhou Stephany E. Shockley Lynne A. Jones Elizabeth A. Griffin Hsiaoju Lee Susan J. Adams Robert H. Mach |
| author_sort | Jonathan McConathy |
| collection | DOAJ |
| description | The ( R )- and ( S )-enantiomers of 2-amino-3-[1-(2-[ 18 F]fluoroethyl)-1 H -[1,2,3]triazol-4-yl]propanoic acid (4) were synthesized and evaluated in the rat 9L gliosarcoma brain tumor model using cell uptake assays, biodistribution studies, and micro-positron emission tomography (microPET). The ( R )- and ( S )-enantiomers of [ 18 F]4 were radiolabeled separately using the click reaction in 57% and 51% decay-corrected yields, respectively. ( S )-[ 18 F]4 was a substrate for cationic amino acid transport and, to a lesser extent, system L transport in vitro. In vivo biodistribution studies demonstrated that ( S )-[ 18 F]4 provided higher tumor uptake and higher tumor to brain ratios (15:1 at the 30- and 60-minute time points) compared to the ( R )-enantiomer (7:1 at the 30- and 60-minute time points). MicroPET studies with ( S )-[ 18 F]4 confirmed that this tracer provides good target to background ratios for both subcutaneous and intracranial 9L gliosarcoma tumors. Based on these results, the 1 H -[1,2,3]triazole-substituted amino acid ( S )-[ 18 F]4 has promising PET properties for brain tumors and represents a novel class of radiolabeled amino acids for tumor imaging. |
| format | Article |
| id | doaj-art-84dd44c1611543ef8828b3197d110b81 |
| institution | Kabale University |
| issn | 1536-0121 |
| language | English |
| publishDate | 2010-11-01 |
| publisher | SAGE Publishing |
| record_format | Article |
| series | Molecular Imaging |
| spelling | doaj-art-84dd44c1611543ef8828b3197d110b812025-01-03T00:11:14ZengSAGE PublishingMolecular Imaging1536-01212010-11-01910.2310/7290.2010.0002510.2310_7290.2010.00025Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission TomographyJonathan McConathyDong ZhouStephany E. ShockleyLynne A. JonesElizabeth A. GriffinHsiaoju LeeSusan J. AdamsRobert H. MachThe ( R )- and ( S )-enantiomers of 2-amino-3-[1-(2-[ 18 F]fluoroethyl)-1 H -[1,2,3]triazol-4-yl]propanoic acid (4) were synthesized and evaluated in the rat 9L gliosarcoma brain tumor model using cell uptake assays, biodistribution studies, and micro-positron emission tomography (microPET). The ( R )- and ( S )-enantiomers of [ 18 F]4 were radiolabeled separately using the click reaction in 57% and 51% decay-corrected yields, respectively. ( S )-[ 18 F]4 was a substrate for cationic amino acid transport and, to a lesser extent, system L transport in vitro. In vivo biodistribution studies demonstrated that ( S )-[ 18 F]4 provided higher tumor uptake and higher tumor to brain ratios (15:1 at the 30- and 60-minute time points) compared to the ( R )-enantiomer (7:1 at the 30- and 60-minute time points). MicroPET studies with ( S )-[ 18 F]4 confirmed that this tracer provides good target to background ratios for both subcutaneous and intracranial 9L gliosarcoma tumors. Based on these results, the 1 H -[1,2,3]triazole-substituted amino acid ( S )-[ 18 F]4 has promising PET properties for brain tumors and represents a novel class of radiolabeled amino acids for tumor imaging.https://doi.org/10.2310/7290.2010.00025 |
| spellingShingle | Jonathan McConathy Dong Zhou Stephany E. Shockley Lynne A. Jones Elizabeth A. Griffin Hsiaoju Lee Susan J. Adams Robert H. Mach Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography Molecular Imaging |
| title | Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography |
| title_full | Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography |
| title_fullStr | Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography |
| title_full_unstemmed | Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography |
| title_short | Click Synthesis and Biologic Evaluation of ()- and ()-2-Amino-3-[1-(2-[F]Fluoroethyl)-1-[1,2,3]Triazol-4-yl]Propanoic Acid for Brain Tumor Imaging with Positron Emission Tomography |
| title_sort | click synthesis and biologic evaluation of and 2 amino 3 1 2 f fluoroethyl 1 1 2 3 triazol 4 yl propanoic acid for brain tumor imaging with positron emission tomography |
| url | https://doi.org/10.2310/7290.2010.00025 |
| work_keys_str_mv | AT jonathanmcconathy clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT dongzhou clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT stephanyeshockley clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT lynneajones clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT elizabethagriffin clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT hsiaojulee clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT susanjadams clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography AT roberthmach clicksynthesisandbiologicevaluationofand2amino312ffluoroethyl1123triazol4ylpropanoicacidforbraintumorimagingwithpositronemissiontomography |