Synthesis of boron cluster lipids:: closo-dodecaborate as an alternative hydrophilic function of boronated liposomes for neutron capture therapy

被引：85

作者：

Lee, Jong-Dae ^{[1
]}

Ueno, Manabu ^{[1
]}

Miyajima, Yusuke ^{[1
]}

Nakamura, Hiroyuki ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 02期

关键词：

D O I：

10.1021/ol062840+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] We succeeded in the synthesis of the double-tailed boron cluster lipids 4a-c and 5a-c, which have a B12H11S moiety as a hydrophilic function, by S-alkylation of B12H11SH (BSH) with bromoacetyl and chloroacetocarbamate derivatives of diacylglycerols for a liposomal boron delivery system on neutron capture therapy. Calcein encapsulation experiments revealed that the liposomes, prepared from the boron cluster lipid 4b, DMPC, PEG-DSPE, and cholesterol, are stable at 37 degrees C in FBS solution for 24 h.

引用

页码：323 / 326

页数：4

共 34 条

[1] DICESIUM N-SUCCINIMIDYL 3-(UNDECAHYDRO-CLOSO-DODECABORANYLDITHIO)PROPIONATE, A NOVEL HETEROBIFUNCTIONAL BORONATING AGENT [J].

ALAM, F ;

SOLOWAY, AH ;

MCGUIRE, JE ;

BARTH, RF ;

CAREY, WE ;

ADAMS, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (04) :522-525

[2] New possibilities of 1,2,4-triazines functionalization: first examples of synthesis and structure of boron-containing 1,2,4-triazines [J].

Azev, Y ;

Lork, E ;

Duelcks, T ;

Gabel, D .

TETRAHEDRON LETTERS, 2004, 45 (16) :3249-3252

[3]

BARTH RF, 1992, CANCER-AM CANCER SOC, V70, P2995

[4]

BARTH RF, 1990, CANCER RES, V50, P1061

[5] Boron-containing polyamines as DNA targeting agents for neutron capture therapy of brain tumors: Synthesis and biological evaluation [J].

Cai, JP ;

Soloway, AH ;

Barth, RF ;

Adams, DM ;

Hariharan, JR ;

Wyzlic, IM ;

Radcliffe, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3887-3896

[6]

DUZGUNES N, 2002, LIPOSOMES, P105

[7] SELECTIVE BORON DELIVERY TO MURINE TUMORS BY LIPOPHILIC SPECIES INCORPORATED IN THE MEMBRANES OF UNILAMELLAR LIPOSOMES [J].

FEAKES, DA ;

SHELLY, K ;

HAWTHORNE, MF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (05) :1367-1370

[8] SYNTHESIS OF S-ALKYL AND S-ACYL DERIVATIVES OF MERCAPTOUNDECAHYDRODODECABORATE, A POSSIBLE BORON CARRIER FOR NEUTRON-CAPTURE THERAPY [J].

GABEL, D ;

MOLLER, D ;

HARFST, S ;

ROSLER, J ;

KETZ, H .

INORGANIC CHEMISTRY, 1993, 32 (11) :2276-2278

[9] Development and in vitro studies of epidermal growth factor-dextran conjugates for boron neutron capture therapy [J].

Gedda, L ;

Olsson, P ;

Ponten, J ;

Carlsson, J .

BIOCONJUGATE CHEMISTRY, 1996, 7 (05) :584-591

[10] NEUTRON-CAPTURE THERAPY OF HUMAN CANCER - INVIVO RESULTS ON TUMOR-LOCALIZATION OF BORON-10-LABELED ANTIBODIES TO CARCINOEMBRYONIC ANTIGEN IN THE GW-39 TUMOR-MODEL SYSTEM [J].

GOLDENBERG, DM ;

SHARKEY, RM ;

PRIMUS, FJ ;

MIZUSAWA, E ;

HAWTHORNE, MF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1984, 81 (02) :560-563

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