Synthesis and evaluation of polyhydroxylated near-infrared carbocyanine molecular probes.

[reaction: see text] A new near-infrared (NIR) fluorescent molecular probe derived from indocarbocyanine dye and galactose was prepared, and the procedure was optimized. The presence of a nonionic polyhydroxyl moiety between hydrophobic groups enhances solubility and possibly minimizes aggregation in aqueous solutions. The structural framework of this molecule provides multivalent sites for labeling diverse molecules.

[1]  R. Weissleder,et al.  High efficiency synthesis of a bioconjugatable near-infrared fluorochrome. , 2003, Bioconjugate chemistry.

[2]  L. Strekowski,,et al.  Substitution reactions of a nucleofugal group in heptamethine cyanine dyes. Synthesis of an isothiocyanato derivative for labeling of proteins with a near-infrared chromophore , 1992 .

[3]  C. J. Lewis,et al.  Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. , 1993, Bioconjugate chemistry.

[4]  K. Drexhage,et al.  Stable heptamethine pyrylium dyes that absorb in the infrared , 1977 .

[5]  Eva M Sevick-Muraca,et al.  Fluorescence-enhanced, near infrared diagnostic imaging with contrast agents. , 2002, Current opinion in chemical biology.

[6]  Samuel Achilefu,et al.  Synthesis, in vitro receptor binding, and in vivo evaluation of fluorescein and carbocyanine peptide-based optical contrast agents. , 2002, Journal of medicinal chemistry.

[7]  T. Smith,et al.  J-aggregate formation of a carbocyanine as a quantitative fluorescent indicator of membrane potential. , 1991, Biochemistry.

[8]  G. Patonay,et al.  A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels , 1995 .

[9]  L. Strekowski,,et al.  Spectral characterization of a novel near-infrared cyanine dye: a study of its complexation with metal ions. , 1998, Talanta.

[10]  V. Ntziachristos,et al.  Concurrent MRI and diffuse optical tomography of breast after indocyanine green enhancement. , 2000, Proceedings of the National Academy of Sciences of the United States of America.

[11]  V. Egorov.  Nature of the optical transition in polymethine dyes and J-aggregates , 2002 .

[12]  S. Achilefu,et al.  Novel receptor-targeted fluorescent contrast agents for in vivo tumor imaging. , 2000, Investigative radiology.

[13]  Yunpeng Ye,et al.  Synthesis and characterization of a macrocyclic near-infrared optical scaffold. , 2003, Journal of the American Chemical Society.

[14]  N. Serpone,et al.  Photophysics of Cyanine Dyes: Subnanosecond Relaxation Dynamics in Monomers, Dimers, and H- and J-Aggregates in Solution , 1997 .