11C-labeling reactions promoted by quaternary ammnonium fluorides and their application for PET studies

• Project/Area Number: 23510289
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical biology
• Research Institution: National Center of Neurology and Psychiatry
• Principal Investigator: KATO KOICHI 独立行政法人国立精神・神経医療研究センター, 脳病態統合イメージングセンター, 室長 (50382198)
• Project Period (FY): 2011 – 2013
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: ＰＥＴ / ＴＢＡＦ / アミノ酸 / AIB / MALA / 早期診断 / 光線力学療法 / 腫瘍ＰＥＴ / 血液脳関門 / テトラブチルアンモニウムフルオリド / アミノイソ酪酸 / アミノレブリン酸 / イブプロフェン / 炭素１１ / 四級アンモニウムフルオリド

Research Abstract

In this study, tetrabutylammonium fluoride (TBAF) was found to be a suitable base for the 11C-methylation reaction of versatile active methylene compounds. The TBAF-promoted 11C-methylation was useful for one-pot synthesis of 11C-labeled aminoisobutyric acid (11C-AIB) and 11C-labeling of ibuprofen. A novel 11C-labeled 5-aminolevulinic acid analog 11C-MALA was also developed. We evaluated these tracers by small animal PET studies. We found that 11C-AIB was a promising tracer for diagnosis of radiation therapy and 11C-MALA-PET was useful for prediction of PDT or SDT of cancers.

Research Products

• [Journal Article] One-pot sequential reactions for the synthesis of versatile 11C-labeled olefin frameworks (2013)
  • Author(s): Takashima M, Kato K, Ogawa M, Magata Y
  • Journal Title: RSC Adv. Volume: 3 Issue: 44 Pages: 21275-79
  • DOI: 10.1039/c3ra43636e
  • Peer Reviewed
• [Journal Article] The use tetrabutylammonium fluoride to promote N- and O-11C-methylation reactions with iodo[11C]methane in DMSO (2013)
  • Author(s): Kikuchi T, Minegishi K, Hashimoto H, Zhang MR, Kato K
  • Journal Title: J. Label. Compd. Radiopharm. Volume: 56 Issue: 13 Pages: 672-678
  • DOI: 10.1002/jlcr.3092
  • Peer Reviewed
• [Journal Article] Synthesis and in vitro cellular uptake of 11C-labeled 5-aminolevulinic acid derivative to estimate the induced cellular accumulation of protoporphyrin IX (2013)
  • Author(s): Suzuki C, Kato K, Tsuji AB, Kikuchi T, Zhang MR, Arano Y, Saga T
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: 23 Pages: 4567-70
  • Peer Reviewed
• [Journal Article] Comparison of 2-amino-[3-11C]isobutyric acid and 2-deoxy-2-[18F]fluoro-D-glucose in nude mice with xenografted tumors and acute inflammation (2012)
  • Author(s): Tsuji AB, Kato K, Sugyo A, Okada M, Sudo H, Yoshida C, Wakizaka H, Zhang MR, Saga T
  • Journal Title: Nucl. Med. Commun. Volume: 33 Issue: 10 Pages: 1058-1064
  • DOI: 10.1097/mnm.0b013e328356efb0
  • Peer Reviewed
• [Journal Article] Efficient synthesis and chiral separation of 11C-labeled ibuprofen assisted by DMSO for imaging of in vivo behavior of the individual isomers by positron emission tomography (2011)
  • Author(s): Kikuchi T, Okada M, Nengaki N, Furutsuka K, Wakizaka H, Okamura T, Zhang MR, Kato K
  • Journal Title: Bioorg. Med. Chem. Volume: 19 Pages: 3265-3273
  • Peer Reviewed
• [Journal Article] An Efficient and Expedient Method for the Synthesis of 11C-labeled α-Aminoisobutyric Acid: A Tumor Imaging Agent Potentially Useful for Cancer Diagnosis (2011)
  • Author(s): Kato K, Tsuji AB, Saga T, Zhang MR
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: 21 Issue: 8 Pages: 2437-2440
  • DOI: 10.1016/j.bmcl.2011.02.065
  • Peer Reviewed
• [Journal Article] Nitroaldol reaction of nitro[11C]methane to form 2-(hydroxymethyl)-2-nitro[2-11C]propa ne-1,3-diol and [11C]Tris (2011)
  • Author(s): Kato K, Zhang MR, Minegishi K, Nengaki N, Takei M, Suzuki K
  • Journal Title: J. Label. Compd. Radiophram. Volume: 54 Issue: 3 Pages: 140-144
  • DOI: 10.1002/jlcr.1833
  • Peer Reviewed
• [Journal Article] [11C]Sorafenib: radiosynthesis and preliminary PET study of brain uptake mediated by P-glucoprotein and breast cancer resistance protein (2011)
  • Author(s): Asakawa C, Ogawa M, Kumata K, Fujinaga M, Kato K, Yamasaki T, Yui J, Kawamura K, Hatori A, Fukumura T, Zhang MR
  • Journal Title: Bioorg. Med. Chem. Lett. Volume: 21 Pages: 2220-2223
  • Peer Reviewed
• [Presentation] Synthesis of 11C-labelled α-methyl profens for COX2 imaging by PET (2013)
  • Author(s): Kato K, Shukuri, M. Kikuchi T, Funasaka M, Hanakawa T
  • Organizer: 20th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: ICC Jeju, Jeju Korea
• [Presentation] Synthesis of 11C-labelled α-methyl profens for COX2 imaging by PET (2013)
  • Author(s): Kato K, Shukuri, M. Kikuchi T, Funasaka M, Hanakawa T
  • Organizer: 20th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: ICC Jeju, Juju, Korea
• [Presentation] ＢＢＢ透過性のイメージング (2013)
  • Author(s): 加藤孝一
  • Organizer: ＰＥＴサマーセミナー２０１３
  • Place of Presentation: ホテル日航金沢、金沢
• [Presentation] DMSO中におけるTBAFを塩基として用いた[11C]H3IによるN-およびO-11C-メチル化 (2013)
  • Author(s): 菊池達矢、峰岸克行、橋本裕輝、張明栄、加藤孝一
  • Organizer: 第５３回日本核医学会学術総会
  • Place of Presentation: 福岡国際会議場、福岡
• [Presentation] 2-Amino-[3-11C]isobutyric acidおよび[N-methyl-11C]alpha-methylaminoisobutyric acidによる血液脳関門の高感度PETイメージング (2013)
  • Author(s): 岡田真希、辻厚至、菊池達矢、脇坂秀克、岡村敏充、加藤孝一、張明栄
  • Organizer: 第５３回日本核医学会学術総会
  • Place of Presentation: 福岡国際会議場、福岡
• [Presentation] 5-アミノレブリン酸を使用した光線力学療法の治療効果を予測するPETプローブの開発に関する基礎的検討 (2013)
  • Author(s): 鈴木千恵、辻厚至、加藤孝一、菊池達矢、須尭綾、須藤仁美、荒野泰、佐賀恒夫
  • Organizer: 第133回日本薬学会年会
  • Place of Presentation: パシフィコ横浜，横浜
• [Presentation] Efficient 11C-methylation of α-nitroesters by mileder base (2012)
  • Author(s): Kato K, Kikuchi T, Minegishi K, Okada M, Zhang MR
  • Organizer: 11th International Symposium on the Synthesis and Applications of Isotopically Labelled Compounds
  • Place of Presentation: Heidelberg University, Heidelberg Germany
• [Presentation] One-pot sequential reaction: simple and efficient methodology for the preparation of 11C-labeled molecular framework (2012)
  • Author(s): Takashima-Hirano M, Magata Y, Kato K
  • Organizer: 11th International Symposium on the Synthesis and Application of Isotopically Labelled Compounds
  • Place of Presentation: Heidelberg University, Heidelberg Germany
• [Presentation] Efficient 11C-Mnethylation of α-nitroesters by milder base (2012)
  • Author(s): Kato K, Kikuchi T, Minegishi K, Okada M, Zhang MR
  • Organizer: 11th International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds
  • Place of Presentation: Heidelberg University, Heidelberg, Germany
• [Presentation] One-pot Sequential Reaction: Simple and Efficient Methodology for the Preparation of 11C-labeled Molecular Framework (2012)
  • Author(s): Takashima-Hirano M, Magata Y, Kato K
  • Organizer: 11th International Symposium on the Synthesis and Applications of Isotopes and Isotopically Labelled Compounds
  • Place of Presentation: Heidelberg University, Heidelberg, Germany
• [Presentation] Development of a PET Probe for Imaging of Organic Anion Transporters (2012)
  • Author(s): Kikuchi T, Okada M, Okamura T, Yui J, Kato K, Fukumura T
  • Organizer: 5th Annual World Molecular Imaging Congress
  • Place of Presentation: Convention Center, Dublin, Ireland
• [Presentation] In Vivo Imaing of Blood Brain Barrier Permeablity with 2-Amino-[3-11C]isobutyric Acid by Positron Emission Tomography (2012)
  • Author(s): Okada M, Tsuji AB, Kikuchi T, Wakizaka H, Okamura T, Zhang MR, Fukumura T, Kato K
  • Organizer: 5th Annual World Molecular Imaging Congress
  • Place of Presentation: Convention Center, Dublin, Ireland
• [Presentation] 2-Amino-[3-11C]isobutyric acidによる血液脳関門の高感度PETイメージング (2012)
  • Author(s): 岡田 真希，辻 厚至，菊池 達矢，脇坂 秀克，岡村 敏充，張 明栄，加藤孝一
  • Organizer: 第52回日本核医学会学術総会
  • Place of Presentation: ニトリ文化ホール，札幌
• [Presentation] ワンポット多段階11C標識合成法の開発 (2012)
  • Author(s): 高島好聖，間賀田泰寛，加藤孝一
  • Organizer: 第52回日本核医学会学術総会
  • Place of Presentation: ニトリ文化ホール，札幌
• [Presentation] 炭素１１で標識されたニトロメタンのMichael付加反応 (2012)
  • Author(s): 加藤孝一, 峯岸克行，張明栄
  • Organizer: 第131回日本薬学会年会
  • Place of Presentation: 北海道大学 （北海道）
• [Presentation] Expedient synthesis and revaluation of 11C-labeled AIB (2011)
  • Author(s): Kato K, Tsuji AB, Saga T, Kikuchi T, Zhang MR
  • Organizer: XII Turku PET Symposium
  • Place of Presentation: ICT building, Turku Finland
• [Presentation] The use of TBAHF2 as a milder fluoride base for [11C]methylation (2011)
  • Author(s): Kato K, Kikuchi T, Minegishi K, Okada M, Zhang MR
  • Organizer: 19th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam Netherland
• [Presentation] Preparation and PET study of individual isomers of [11C]ibuprofen (2011)
  • Author(s): Okada M, Kikuchi T, Nengaki N, Fukumura T, Wakizaka H, Okamura T, Zhang MR, Kato K
  • Organizer: International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam Netherland
• [Presentation] 炭素11で標識されたニトロメタンのMichael付加反応 (2011)
  • Author(s): 加藤孝一,峯岸克行,張明栄
  • Organizer: 第131回日本薬学会年会
  • Place of Presentation: 北海道大学,札幌
• [Presentation] Expedient synthesis and revaluation of 11C-labeled AIB (2011)
  • Author(s): Kato K, Tsuji AB, Saga T, Kikuchi T, Zhang MR
  • Organizer: XII Turku PET Symposium
  • Place of Presentation: ICT building, Turku, Finland
• [Presentation] 2-Amino-[3-11C]isobutyric acid as an in vivo imaging agent for the assessment of blood-brain barrier permeability (2011)
  • Author(s): Okada M, Kikuchi T, Wakizaka H, Tsuji AB, Okamura T, Zhang MR, Kato K
  • Organizer: Brain and Brain PET 2011
  • Place of Presentation: Centre de Convencions Internacional de Barcelona, Barcerona, Spain
• [Presentation] Efficient radiosynthesis of [11C]sorafenib using [11C]phosgene as a labeling agent (2011)
  • Author(s): Asakawa C, Ogawa M, Kumata K, Fujinaga M, Kato K, Yamasaki T, Yui J, Hatori A, Fukumura T, Zhang MR
  • Organizer: 19th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam, Netherland
• [Presentation] The use of TBAHF2 as a milder fluoride base for the [11C]methylation (2011)
  • Author(s): Kato K, Kikuchi T, Minegishi K, Okada M, Zhang MR
  • Organizer: 19th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam, Netherland
• [Presentation] Preparation and PET study of individual isomers of [11C]ibuprofen (2011)
  • Author(s): Okada M, Kikuchi T, Nengaki N, Furutsuka K, Wakizaka H, Okamura T, Zhang MR, Kato K
  • Organizer: 19th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam, Netherland
• [Presentation] Assessment of 11C-2-aminoisobutyric acid in nude mice with tumor and inflammation (2011)
  • Author(s): Tsuji AB, Kato K, Sugyo A, Sudo H, Yoshida C, Zhang MR, Saga T
  • Organizer: 19th International Symposium on Radiopharmaceutical Sciences
  • Place of Presentation: VU University, Amsterdam, Netherland
• [Patent(Industrial Property Rights)] 11C標識アミノ酸類縁体の製造方法および核医学画像診断薬 (2011)
  • Inventor(s): 加藤孝一
  • Industrial Property Rights Holder: 放射線医学総合研究所
  • Filing Date: 2011