P-1-076(Write the presentation numberin pencil at the top left-hand corner.)

2.5cm

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2.5cm

2.5cm

Study of the Fluorine- and Boron-1018Containing
pt. bold
pt. line spacing)
BNCT
4 pt. superscript Compounds toward MRI and(18
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(10 pt. size)
132,pt.
bold
Yoshihide Hattori1, Yoshihiro Yamaguchi1, Hitoshi Yamamoto
Tomohiro
Asano3,1
pt. line spacing)
Mitsunori Kirihata3, Masao Takagaki4, and Tateaki(13Wakamiya
Center on
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the page. 1Faculty of Science and Technology, Kinki University, Higashi-osaka Osaka 577-8502,
13 pt. italicJapan, 2Graduate School of Science, Osaka University, Toyonaka,
Osaka 560-0043,
Japan, 3College of Agriculture, University of Osaka Prefecture,
Osaka(13 pt. lineSakai,spacing)599-8231, Japan, 4Department of Neurosurgery, Aino Junior College Hospital, Ibaraki
Osaka 567-0018, Japan
Only one correspondence
e-mail: vagrants@mail.goo.ne.jp
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e-mail address. (13 pt. bold)
Magnetic resonance imaging (MRI) and boron-neutron capture therapy (BNCT)5-7 linesof 12 pt.anditalics(Line of cancer, respectively.
are quite attractive techniques
for diagnosis
treatment
spacingat 13
andforcenter
In order to develop thepracticaltoolspt.)
both
MRI and BNCT, the novel
10withmargins.
compounds containing justify
both 19F
and1cm
B atoms
in a single molecule were designed
Word paper
originallyin italics
the syntheses
and the internalization rates 1cm
1cm and synthesized. In the present
into tumor cells of thesecompounds
arefont.
elucidated. Furthermore, their 19F
shouldbe in plain
12 pt. bold NMR measurements are also reported.

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Keywords: boron neutron capture therapy (BNCT), 12
3-(4-boronophenyl)alaninept.
(Bpa), 3-(4-borono-2,6-difluorophenyl)alanine [Bpa(F
3-(4-borono-2,6-di(132)],
pt. linespacing)fluorophenyl)alaninol [Bpa(F2)-ol], magnetic resonance imaging (MRI)

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1.25 cm indent
Introduction
Type13 pt. hading
in bold. the magnetic resonance imaging
According to ourpreliminary
elucidation,No.
19 space for the following text.
(MRI) based on theF NMR measurement of the dipeptides containing
3-(4-fluorophenyl)alanine [Phe(F)] internalized into tumor cells may be accessible as aType all characters in 13 pt.
promising means for diagnosis of cancer.
’TimesNeworRoman’
font with
From the standpoint of a treatment of brain
cancermelanoma,the boron
exactly 13 pt.
10 line spacing.
neutron capture therapy (BNCT) based on the interaction of B isotope and thermal
neutron has been highly noted in recent years [1-3]. In order to develop practical
tools for not only MRI but also BNCT, we designed and synthesized the novelcompounds containing both 19F and 10B atoms in a single molecule.
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Results and Discussion
At present 3-(4-boronophenyl)alanine (Bpa) (1) [4] and 3-(4-boronophenyl)alaninol (Bpa-ol) (2) [5] enriched with 10B isotope seem to be good candidates
for BNCT as the 10B carrier. In the present study we carried out the synthesis of(Write the page number in pencil
3.0cm
at the bottom right-hand corner.)

SPECIMEN12.5cm
two novel compounds containing both 19F and 10B atoms in a single molecule such as[Bpa(F2)-10B] (3) and 3-(4-borono-2,6-difluo- 2.5cm
2.5cm 3-(4-borono-2,6-difluorophenyl)alaninerophenyl)alaninol [Bpa(F2)-10B-ol] (4); these compounds may be useful for not only
MRI but also BNCT (Fig. 1).
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H2NHOH 2N

CO2H

HO

10B
OH

H2N
F

CH2OHHO

10

Type in 13 pt. italics.

HO10FBOH

BOH

1H2N
F

CO2H

2

CH2OH

10F

BOH34

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Fig. 1. Bpa-10B (1) and the related compounds 2 ~ 4.
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FFF

1) BuLi, TMP / THF
Br2) CO2 , H2O / THF
73.9%

F

5F

TBDMS-Cl
Imidazole / DMF
90.4%

FBrB
OH

OTBDMSi2) NaBH4, H2O / THF
94.8%

FF

MgCl2) PBr3 / Et2O

HO10B
OH

94.2%

9OTBDMS

10F/ iPrOH
70.5%

Draw directly. Figures NHAc
should beCH(COOEt)2F
placedatthetoporbottomofAcNHCH(COOEt)2the page,
60%NaH/ THF if possible.
HO10F

B
OH

92.7%

COOH

11BocHNF

COOH

Boc2O, Na2CO3HO10F

BOH

H2O, MeOH

HO10OH

12CH2OH

BocHN
F

1) ClCOOEt, NMM / THF
HO

Type80.1%
in 13 pt. italics.

HCl.H2NF

4M HCl / AcOEt
HO10F

B
OH

13F

Bquant32) NaBH4, MeOH / THF

B(OMe)3
THF
93.7 %

10
H2N
F

O

BrF

1) 6M HCl : AcOH = 1 : 12)

F

78F

OH

BrPrMgClTHF

OTBDMSFF61) 66% AcOH

101) IPCF, Et3N / THF

SPECIMENBr

HOCOOH

92.6%

10CH2OH

FBOH4

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Fig. 2. Synthetic scheme of Bpa(F2)-10B (3) and Bpa(F2)-10B-ol (4).
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3.0cm(Write the page number in pencil
at the bottom right-hand corner.)22.5cmReferences
1. Kato, I., Ono, K., Sakurai, Y., Ohmae, M., Maruhashi, A., Imahori, Y., Kirihata,
2.5cm
2.5cm
M., Nakazawa, M., and Yura, Y. (2004) Appl. Radiat. Isot., 61, 1083-1087.
2. Barth, R. F., Yang, W., Adams, D. M., Rotaru, J. H., Shukla, S., Sekido, M.,Tjarks, W., Fenstermaker, R. A., Ciesielski, M., Nawrocky, M. M., and Coderre, J.
A. (2002) Cancer Res., 62, 3159-3166.
3. Kane, R. R., Drechsel, K., and Hawthorne, M. F. (1993) J. Am. Chem. Soc., 115,8853-8854.
4. Nakao, H., Morimoto, T., and Kirihata, M. (1996) Biosci. Biotec. Biochem., 60,683-684.
5. Masunaga, S., Ono, K., Kirihata, M., Takagaki, M., Sakurai, Y., Kinashi, Y.,
Kobayashi, T., Nagasawa, H., Uto, Y., and Hori, H. (2001) Jpn. J. Cancer Res., 92,996-1007.

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