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      Advancing BNCT: A Concise Review on 18F Labeling of Tracers

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      https://www.riss.kr/link?id=A109907475

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      다국어 초록 (Multilingual Abstract) kakao i 다국어 번역

      Boron neutron capture therapy (BNCT) stands at the forefront of cancer treatment, offering a pioneering approach to enhance the rate of recovery for patients who show noncompliance to conventional therapies.
      The 18F labeling of BNCT tracers signifies a groundbreaking leap in molecular imaging. Hence, the aim of this brief review is to outline the radiofluorination strategies utilized for BNCT tracers. Radiofluorination of L-BPA, a ligand of L-type amino acids, can be carried out via electrophilic as well as nucleophilic substitution reactions.
      It’s solubility can be elevated by complexing it with fructose to form BPA-fructose complex, followed by radiolabeling with 18F. In addition to electrophilic and nucleophilic radiofluorination, we have briefly presented the radiofluoro exchange method, which is applicable for amino acids having trifluoroborate groups, i.e., FBY (fluoroboronotyrosine), featuring both imaging and therapeutic functionalities. Furthermore, this review offers an inclusive array of radiofluorination strategies employed for other BNCT tracers, including o-carborane and fenbufen boronopinacol.
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      Boron neutron capture therapy (BNCT) stands at the forefront of cancer treatment, offering a pioneering approach to enhance the rate of recovery for patients who show noncompliance to conventional therapies. The 18F labeling of BNCT tracers signifies ...

      Boron neutron capture therapy (BNCT) stands at the forefront of cancer treatment, offering a pioneering approach to enhance the rate of recovery for patients who show noncompliance to conventional therapies.
      The 18F labeling of BNCT tracers signifies a groundbreaking leap in molecular imaging. Hence, the aim of this brief review is to outline the radiofluorination strategies utilized for BNCT tracers. Radiofluorination of L-BPA, a ligand of L-type amino acids, can be carried out via electrophilic as well as nucleophilic substitution reactions.
      It’s solubility can be elevated by complexing it with fructose to form BPA-fructose complex, followed by radiolabeling with 18F. In addition to electrophilic and nucleophilic radiofluorination, we have briefly presented the radiofluoro exchange method, which is applicable for amino acids having trifluoroborate groups, i.e., FBY (fluoroboronotyrosine), featuring both imaging and therapeutic functionalities. Furthermore, this review offers an inclusive array of radiofluorination strategies employed for other BNCT tracers, including o-carborane and fenbufen boronopinacol.

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      참고문헌 (Reference)

      1 Lemaire C, 44 : 737-, 1991

      2 Gona KB, "[¹⁸F]Fluorination of o-carborane via nucleophilic substitution : towards a versatile platform for the preparation of ¹⁸F-labelled BNCT drug candidates" 49 (49): 2013

      3 Lan TL, "Using salvage Boron Neutron Capture Therapy(BNCT)for recurrent malignant brain tumors in Taiwan" 160 : 109105-, 2020

      4 Rose PB, "Uncovering special nuclear materials by low-energy nuclear reaction imaging" 6 (6): 24388-, 2016

      5 Hawthorne MF, "The role of chemistry in the development of boron neutron capture therapy of cancer" 32 (32): 950-984, 1993

      6 Stöcklin G, "The impact of radioactivity on medicine metallic" 70 (70): 249-272, 1995

      7 Vähätalo JK, "Synthesis of 4-dihydroxyboryl-2-[18F] fluorophenylalanine with relatively high-specific activity" 45 (45): 697-704, 2002

      8 Miller PW, "Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography" 47 (47): 8998-9033, 2008

      9 Ishiwata K, "Synthesis and radiation dosimetry of 4-borono-2-[18F]fluoro-D, L-phenylalanine : a target compound for PET and boron neutron capture therapy" 42 (42): 325-328, 1991

      10 Yeh CN, "Synthesis and characterization of boron fenbufen and its F-18 labeled homolog for boron neutron capture therapy of COX-2 overexpressed cholangiocarcinoma" 107 : 217-229, 2017

      1 Lemaire C, 44 : 737-, 1991

      2 Gona KB, "[¹⁸F]Fluorination of o-carborane via nucleophilic substitution : towards a versatile platform for the preparation of ¹⁸F-labelled BNCT drug candidates" 49 (49): 2013

      3 Lan TL, "Using salvage Boron Neutron Capture Therapy(BNCT)for recurrent malignant brain tumors in Taiwan" 160 : 109105-, 2020

      4 Rose PB, "Uncovering special nuclear materials by low-energy nuclear reaction imaging" 6 (6): 24388-, 2016

      5 Hawthorne MF, "The role of chemistry in the development of boron neutron capture therapy of cancer" 32 (32): 950-984, 1993

      6 Stöcklin G, "The impact of radioactivity on medicine metallic" 70 (70): 249-272, 1995

      7 Vähätalo JK, "Synthesis of 4-dihydroxyboryl-2-[18F] fluorophenylalanine with relatively high-specific activity" 45 (45): 697-704, 2002

      8 Miller PW, "Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography" 47 (47): 8998-9033, 2008

      9 Ishiwata K, "Synthesis and radiation dosimetry of 4-borono-2-[18F]fluoro-D, L-phenylalanine : a target compound for PET and boron neutron capture therapy" 42 (42): 325-328, 1991

      10 Yeh CN, "Synthesis and characterization of boron fenbufen and its F-18 labeled homolog for boron neutron capture therapy of COX-2 overexpressed cholangiocarcinoma" 107 : 217-229, 2017

      11 Ainslie-McLaren G, "Red cell volume measurement–using indium as a replacement for chromium" 41 (41): 589-596, 2020

      12 Madsen MT, "Recent advances in SPECT imaging" 48 (48): 661-673, 2007

      13 Deng JP, "Recent Development of Radiofluorination of Boron Agents for Boron Neutron Capture Therapy of Tumor : Creation of 18F-Labeled CF and BF Linkages" 16 (16): 93-, 2023

      14 Scroggie KR, "Reaction of [18F]fluoride at heteroatoms and metals for imaging of peptides and proteins by positron emission tomography" 9 : 687678-, 2021

      15 Gona KB, "Radiolabeling Strategies for Boron Clusters : Toward Fast Development and Efficient Assessment of BNCT Drug Candidates" 232-267, 2018

      16 Gona KB, "Radiolabeling Strategies for Boron Clusters : Toward Fast Development and Efficient Assessment of BNCT Drug Candidates" 232-267, 2018

      17 Imahori Y, "Positron emission tomography-based boron neutron capture therapy using boronophenylalanine for high-grade gliomas : Part II" 4 (4): 1833-1841, 1998

      18 Farhood B, "Physical, dosimetric and clinical aspects and delivery systems in neutron capture therapy" 23 (23): 462-473, 2018

      19 Coenen HH, "PET Chemistry: The Driving Force in Mol Imag" 15-50, 2007

      20 Confalonieri L, "Organotrifluoroborate Sugar Conjugates for a Guided Boron Neutron Capture Therapy : From Synthesis to Positron Emission Tomography" 7 (7): 48340-48348, 2022

      21 Krasikova RN, "Nucleophilic synthesis of 6-l-[18F] FDOPA. Is copper-mediated radiofluorination the answer?" 25 (25): 4365-, 2020

      22 He J, "Nucleophilic radiosynthesis of boron neutron capture therapy-oriented PET probe [18F] FBPA using aryldiboron precursors" 57 (57): 8953-8956, 2021

      23 He J, "Nucleophilic radiosynthesis of boron neutron capture therapy-oriented PET probe [18F] FBPA using aryldiboron precursors" 57 (57): 8953-8956, 2021

      24 Hicks RJ, "Is there still a role for SPECT–CT in oncology in the PET–CT era?" 9 (9): 712-720, 2012

      25 Basu S, "Fundamentals of PET and PET/CT imaging" 1228 (1228): 1-8, 2011

      26 Liu Z, "From minutes to years : predicting organotrifluoroborate solvolysis rates" 21 (21): 3924-3928, 2015

      27 Kirk KL, "Fluorination in medicinal chemistry : methods, strategies, and recent developments" 12 (12): 305-321, 2008

      28 Gona KB, "Exploring new labelling strategies for boronated compounds: towards fast development and efficient assessment of BNCT drug candidates" 2015

      29 Kabalka GW, "Evaluation of fluorine-18-BPA-fructose for boron neutron capture treatment planning" 38 (38): 1762-1767, 1997

      30 Tsukada H, "Evaluation of D-isomers of O-18 F-fluoromethyl, O-18 F-fluoroethyl and O-18 F-fluoropropyl tyrosine as tumour imaging agents in mice" 33 : 1017-1024, 2006

      31 Lakshminarayana G, "Estimation of gamma-rays, and fast and the thermal neutrons attenuation characteristics for bismuth tellurite and bismuth boro-tellurite glass systems" 55 : 5750-5771, 2020

      32 Chang TY, "Comparison of the synthesis and biological properties of no-carrier-added and carrieradded 4-borono-2-[18F] fluorophenylalanine([18F] FBPA)" 116 : 108313-, 2023

      33 Suzuki M, "Boron neutron capture therapy(BNCT) : A unique role in radiotherapy with a view to entering the accelerator-based BNCT era" 25 (25): 43-50, 2020

      34 Evangelista L, "Boron neutron capture therapy and 18F-labelled borophenylalanine positron emission tomography : A critical and clinical overview of the literature" 74 : 91-101, 2013

      35 Ali F, "Boron chemistry for medical applications" 25 (25): 828-, 2020

      36 Wittig A, "Boron analysis and boron imaging in biological materials for boron neutron capture therapy(BNCT)" 68 (68): 66-90, 2008

      37 Yang Q, "Biodistribution and radiation dosimetry of D-isomer of 4-borono-2-[18F] fluoro-phenylalanine : A comparative PET/CT study with L-isomer in healthy human volunteers" 94 : 32-37, 2021

      38 Li J, "A metabolically stable boron-derived tyrosine serves as a theranostic agent for positron emission tomography guided boron neutron capture therapy" 30 (30): 2870-2878, 2019

      39 Coenen HH, "18F-labelling innovations and their potential for clinical application" 6 (6): 169-193, 2018

      40 Li Z, "18F-Boramino acid PET/CT in healthy volunteers and glioma patients" 1-9, 2021

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