Synthesis of 2′-deoxy-2′-[18F]fluoro-β-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation -: Synthesis of [18F]labeled FAU, FMAU, FBAU, FIAU

被引:107
作者
Mangner, TJ
Klecker, RW
Anderson, L
Shields, AF
机构
[1] Wayne State Univ, Childrens Hosp Michigan, PET Ctr, Detroit, MI 48201 USA
[2] US FDA, Lab Clin Pharmacol, Rockville, MD 20857 USA
[3] Wayne State Univ, Karmanos Canc Inst, Detroit, MI 48201 USA
关键词
fluorine-18; 2 '-[F-18]fluoro-2 '-deoxy-beta-D-arabinofuranosyl nucleosides; FAU; FMAU; FBAU; FIAU;
D O I
10.1016/S0969-8051(02)00445-6
中图分类号
R8 [特种医学]; R445 [影像诊断学];
学科分类号
1002 ; 100207 ; 1009 ;
摘要
An efficient and reliable synthesis of 2'-deoxy-2'-[F-18]fluoro-beta-D-arabinofuranosyl nucleosides is presented. Overall decay-corrected radiochemical yields of 35-45% of 4 analogs, FAU, FMAU, FBAU and FIAU are routinely obtained in >98% radiochemical purity and with specific activities of greater than 3 Ci/mumol (110 MBq/mumol) in a synthesis time of approximately 3 hours. When similar to220 mCi (8.15 GBq) of starting [F-18]fluoride is used, 25-30 mCi (0.93-1.11 GBq) of product (enough to image two patients sequentially) is typically obtained. (C) 2003 Elsevier Science Inc. All rights reserved.
引用
收藏
页码:215 / 224
页数:10
相关论文
共 18 条
[1]   Synthesis of [18F]-labeled 2′-deoxy-2′-fluoro-5-methyl-1-β-D-arabinofuranosyluracil ([18F]-FMAU) [J].
Alauddin, MM ;
Conti, PS ;
Fissekis, JD .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2002, 45 (07) :583-590
[2]   Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters:: preparation of a versatile intermediate for synthesis of 2′-[18F]-fluoro-arabinonucleosides [J].
Alauddin, MM ;
Conti, PS ;
Mathew, T ;
Fissekis, JD ;
Prakash, GKS ;
Watanabe, KA .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 106 (01) :87-91
[3]   Pharmacokinetics of the thymidine analog 2′-fluoro-5-[14C]-methyl-1-β-D-arabinofuranosyluracil ([14C]FMAU) in rat prostate tumor cells [J].
Bading, JR ;
Shahinian, AH ;
Bathija, P ;
Conti, PS .
NUCLEAR MEDICINE AND BIOLOGY, 2000, 27 (04) :361-368
[4]  
Blasberg RG, 1999, Q J NUCL MED, V43, P163
[5]  
Collins JM, 1999, CLIN CANCER RES, V5, P1976
[6]   SYNTHESIS OF 2'-FLUORO-5-[C-11]-METHYL-1-BETA-D-ARABINOFURANOSYLURACIL ([C-11]-FMAU) - A POTENTIAL NUCLEOSIDE ANALOG FOR IN-VIVO STUDY OF CELLULAR PROLIFERATION WITH PET [J].
CONTI, PS ;
ALAUDDIN, MM ;
FISSEKIS, JR ;
SCHMALL, B ;
WATANABE, KA .
NUCLEAR MEDICINE AND BIOLOGY, 1995, 22 (06) :783-789
[7]   ANTIVIRAL NUCLEOSIDES - A STEREOSPECIFIC, TOTAL SYNTHESIS OF 2'-FLUORO-2'-DEOXY-BETA-D-ARABINOFURANOSYL NUCLEOSIDES [J].
HOWELL, HG ;
BRODFUEHRER, PR ;
BRUNDIDGE, SP ;
BENIGNI, DA ;
SAPINO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :85-88
[8]  
Jacobs A, 2001, CANCER RES, V61, P2983
[9]   Evaluation of [76Br]FBAU 3′,5′-dibenzoate as a lipophilic prodrug for brain imaging [J].
Kao, CHK ;
Waki, A ;
Sassaman, MB ;
Jagoda, EM ;
Szajek, LP ;
Ravasi, L ;
Shimoji, K ;
Eckelman, WC .
NUCLEAR MEDICINE AND BIOLOGY, 2002, 29 (05) :527-535
[10]   The sequential syntheses of [76Br]FBAU 3′,5′-dibenzoate and [76Br]FBAU [J].
Kao, CHK ;
Sassaman, MB ;
Szajek, LP ;
Ma, Y ;
Waki, A ;
Eckelman, WC .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2001, 44 (13) :889-898