Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) for PET

Uday Mukhopadhyay; Ashutosh Pal; Juri G. Gelovani; William Bornmann; Mian M. Alauddin

doi:10.1016/j.apradiso.2007.04.003

Radiosynthesis of 2′-deoxy-2′-[¹⁸F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([¹⁸F]-l-FMAU) for PET

Uday Mukhopadhyay, Ashutosh Pal, Juri G. Gelovani, William Bornmann, Mian M. Alauddin

Cancer Systems Imaging

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Radiosynthesis of 2′-deoxy-2′-[¹⁸F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([¹⁸F]-l-FMAU) is reported. Compound 1 was synthesized and converted to 2-triflate 2. Compound 3 was prepared from 2 using tetrabutylammonium[¹⁸F]fluoride, converted to 4, and then coupled with 5. The crude product was hydrolyzed, and purified by HPLC to obtain 7a. The radiochemical yield of [¹⁸F]-l-FMAU was 26% decay corrected (d.c.) in four runs with radiochemical purity >99% and specific activity 2200 mCi/μmol. The synthesis time was 3.3-3.5 h from the end of bombardment (EOB).

Original language	English (US)
Pages (from-to)	941-946
Number of pages	6
Journal	Applied Radiation and Isotopes
Volume	65
Issue number	8
DOIs	https://doi.org/10.1016/j.apradiso.2007.04.003
State	Published - Aug 2007

Keywords

Fluorine-18
Hepatitis B
Nucleoside
l-FMAU

ASJC Scopus subject areas

Radiation

MD Anderson CCSG core facilities

Small Animal Imaging Facility
NMR Facility

Access to Document

10.1016/j.apradiso.2007.04.003

Cite this

@article{7e068a16bca34af8b737dde825935d69,

title = "Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) for PET",

abstract = "Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) is reported. Compound 1 was synthesized and converted to 2-triflate 2. Compound 3 was prepared from 2 using tetrabutylammonium[18F]fluoride, converted to 4, and then coupled with 5. The crude product was hydrolyzed, and purified by HPLC to obtain 7a. The radiochemical yield of [18F]-l-FMAU was 26% decay corrected (d.c.) in four runs with radiochemical purity >99% and specific activity 2200 mCi/μmol. The synthesis time was 3.3-3.5 h from the end of bombardment (EOB).",

keywords = "Fluorine-18, Hepatitis B, Nucleoside, l-FMAU",

author = "Uday Mukhopadhyay and Ashutosh Pal and Gelovani, {Juri G.} and William Bornmann and Alauddin, {Mian M.}",

note = "Funding Information: This work was supported by the start up funds to Mian Alauddin and Juri Gelovani from the University of Texas M D Anderson Cancer Center.",

year = "2007",

month = aug,

doi = "10.1016/j.apradiso.2007.04.003",

language = "English (US)",

volume = "65",

pages = "941--946",

journal = "Applied Radiation and Isotopes",

issn = "0969-8043",

publisher = "Elsevier Limited",

number = "8",

}

TY - JOUR

T1 - Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) for PET

AU - Mukhopadhyay, Uday

AU - Pal, Ashutosh

AU - Gelovani, Juri G.

AU - Bornmann, William

AU - Alauddin, Mian M.

N1 - Funding Information: This work was supported by the start up funds to Mian Alauddin and Juri Gelovani from the University of Texas M D Anderson Cancer Center.

PY - 2007/8

Y1 - 2007/8

N2 - Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) is reported. Compound 1 was synthesized and converted to 2-triflate 2. Compound 3 was prepared from 2 using tetrabutylammonium[18F]fluoride, converted to 4, and then coupled with 5. The crude product was hydrolyzed, and purified by HPLC to obtain 7a. The radiochemical yield of [18F]-l-FMAU was 26% decay corrected (d.c.) in four runs with radiochemical purity >99% and specific activity 2200 mCi/μmol. The synthesis time was 3.3-3.5 h from the end of bombardment (EOB).

AB - Radiosynthesis of 2′-deoxy-2′-[18F]-fluoro-5-methyl-1-β-l-arabinofuranosyluracil ([18F]-l-FMAU) is reported. Compound 1 was synthesized and converted to 2-triflate 2. Compound 3 was prepared from 2 using tetrabutylammonium[18F]fluoride, converted to 4, and then coupled with 5. The crude product was hydrolyzed, and purified by HPLC to obtain 7a. The radiochemical yield of [18F]-l-FMAU was 26% decay corrected (d.c.) in four runs with radiochemical purity >99% and specific activity 2200 mCi/μmol. The synthesis time was 3.3-3.5 h from the end of bombardment (EOB).

KW - Fluorine-18

KW - Hepatitis B

KW - Nucleoside

KW - l-FMAU

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DO - 10.1016/j.apradiso.2007.04.003

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VL - 65

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