Swallowtail bacteriochlorins.: Lipophilic absorbers for the near-infrared

被引:34
作者
Borbas, K. Eszter [1 ]
Ruzie, Christian [1 ]
Lindsey, Jonathan S. [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
关键词
D O I
10.1021/ol800436u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bacteriochlorins absorb strongly in the near-infrared spectral region and hence are ideally suited for diverse photomedical applications, yet naturally occurring bacteriochlorins have limited stability and synthetic malleability. A de novo route has been exploited to prepare synthetic bacteriochlorins that bear a geminal dimethyl group in each pyrroline ring for stability and a symmetrically branched 1,5-dimethoxypentyl group attached to each pyrrole ring for solubility in lipophilic media.
引用
收藏
页码:1931 / 1934
页数:4
相关论文
共 29 条
[1]   Design, synthesis, and photophysical characterization of water-soluble chlorins [J].
Borbas, K. Eszter ;
Chandrashaker, Vanampally ;
Muthiah, Chinnasamy ;
Kee, Hooi Ling ;
Holten, Dewey ;
Lindsey, Jonathan S. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3145-3158
[2]   A compact water-soluble porphyrin bearing an iodoacetamido bioconjugatable site [J].
Borbas, K. Eszter ;
Kee, Hooi Ling ;
Holten, Dewey ;
Lindsey, Jonathan S. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :187-194
[3]   Bioconjugatable porphyrins bearing a compact swallowtail motif for water solubility [J].
Borbas, K. Eszter ;
Mroz, Pawel ;
Hamblin, Michael R. ;
Lindsey, Jonathan S. .
BIOCONJUGATE CHEMISTRY, 2006, 17 (03) :638-653
[4]   Novel water-soluble bacteriochlorophyll derivatives for vascular-targeted photodynamic therapy: Synthesis, solubility, phototoxicity and the effect of serum proteins [J].
Brandis, A ;
Mazor, O ;
Neumark, E ;
Rosenbach-Belkin, V ;
Salomon, Y ;
Scherz, A .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2005, 81 (04) :983-993
[5]   SYNTHESIS OF 4,4-BIS(2-METHOXYETHYL)CYCLOHEXANONE AND OF 4,4-BIS(2-METHOXYETHYL)-2-CYCLOHEXEN-1-ONE [J].
CHEESEMAN, EN .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (04) :519-521
[6]  
Chen Q, 2002, PHOTOCHEM PHOTOBIOL, V76, P438, DOI 10.1562/0031-8655(2002)076<0438:PSINCP>2.0.CO
[7]  
2
[8]   A THEORETICAL AND EXPERIMENTAL-STUDY OF LIGHT-ABSORPTION AND SCATTERING BY INVIVO SKIN [J].
DAWSON, JB ;
BARKER, DJ ;
ELLIS, DJ ;
GRASSAM, E ;
COTTERILL, JA ;
FISHER, GW ;
FEATHER, JW .
PHYSICS IN MEDICINE AND BIOLOGY, 1980, 25 (04) :695-709
[9]   VERY SOLUBLE AND PHOTOSTABLE PERYLENE FLUORESCENT DYES [J].
DEMMIG, S ;
LANGHALS, H .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (02) :225-230
[10]   Regioselective 15-bromination and functionalization of a stable synthetic bacteriochlorin [J].
Fan, Dazhong ;
Taniguchi, Masahiko ;
Lindsey, Jonathan S. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5350-5357