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Synthesis of Cyanine Dyes | SpringerLink

Symmetrical and Asymmetrical Cyanine Dyes. Synthesis, Spectral Properties, and BSA Association Study

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Synthesis and Characterization of Heptamethine Cyanine Dyes

We present the synthesis and characterization of the somatostatin receptor-specific peptide H2N-(D-Phe)-cyclo[Cys-Phe-(D-Trp)-Lys-Thr-Cys]-Thr-OH, which is labeled with a carboxylated indodicarbo- and an indotricarbocyanine dye at the N-terminal amino group. The preparation was performed by automated solid-phase synthesis, with subsequent attachment of the cyanine dye and cleavage of the entire conjugate from the resin. The compounds display high molar absorbance and fluorescence quantum yields typical for cyanine dyes and are thus suitable receptor-targeted contrast agents for molecular optical imaging. The ability of these agents to target the somatostatin receptor was demonstrated by flow cytometry in vitro, in which the indotricarbocyanine conjugate led to elevated cell-associated fluorescence on somatostatin receptor-expressing tumor cells. In contrast, the corresponding linearized derivative of the sequence H2N-(D-Phe)-Met-Phe-(D-Trp)-Lys-Thr-Met-Thr-OH produced only minimal cell fluorescence, hence confirming the specificity of the cyclic somatostatin analogue. Intracellular localization could be visualized by near-infrared (NIR) fluorescence microscopy. In conclusion, receptor-specific peptides are promising tools for designing site-directed optical contrast agents for use in molecular optical imaging.

Synthesis and optical properties of cyanine dyes with …

N2 - We present the synthesis and characterization of the somatostatin receptor-specific peptide H2N-(D-Phe)-cyclo[Cys-Phe-(D-Trp)-Lys-Thr-Cys]-Thr-OH, which is labeled with a carboxylated indodicarbo- and an indotricarbocyanine dye at the N-terminal amino group. The preparation was performed by automated solid-phase synthesis, with subsequent attachment of the cyanine dye and cleavage of the entire conjugate from the resin. The compounds display high molar absorbance and fluorescence quantum yields typical for cyanine dyes and are thus suitable receptor-targeted contrast agents for molecular optical imaging. The ability of these agents to target the somatostatin receptor was demonstrated by flow cytometry in vitro, in which the indotricarbocyanine conjugate led to elevated cell-associated fluorescence on somatostatin receptor-expressing tumor cells. In contrast, the corresponding linearized derivative of the sequence H2N-(D-Phe)-Met-Phe-(D-Trp)-Lys-Thr-Met-Thr-OH produced only minimal cell fluorescence, hence confirming the specificity of the cyclic somatostatin analogue. Intracellular localization could be visualized by near-infrared (NIR) fluorescence microscopy. In conclusion, receptor-specific peptides are promising tools for designing site-directed optical contrast agents for use in molecular optical imaging.

Microwave Synthesis of Cyanine Dyes - ResearchGate

AB - We present the synthesis and characterization of the somatostatin receptor-specific peptide H2N-(D-Phe)-cyclo[Cys-Phe-(D-Trp)-Lys-Thr-Cys]-Thr-OH, which is labeled with a carboxylated indodicarbo- and an indotricarbocyanine dye at the N-terminal amino group. The preparation was performed by automated solid-phase synthesis, with subsequent attachment of the cyanine dye and cleavage of the entire conjugate from the resin. The compounds display high molar absorbance and fluorescence quantum yields typical for cyanine dyes and are thus suitable receptor-targeted contrast agents for molecular optical imaging. The ability of these agents to target the somatostatin receptor was demonstrated by flow cytometry in vitro, in which the indotricarbocyanine conjugate led to elevated cell-associated fluorescence on somatostatin receptor-expressing tumor cells. In contrast, the corresponding linearized derivative of the sequence H2N-(D-Phe)-Met-Phe-(D-Trp)-Lys-Thr-Met-Thr-OH produced only minimal cell fluorescence, hence confirming the specificity of the cyclic somatostatin analogue. Intracellular localization could be visualized by near-infrared (NIR) fluorescence microscopy. In conclusion, receptor-specific peptides are promising tools for designing site-directed optical contrast agents for use in molecular optical imaging.

Abstract: A series of meso-chlorine substituted heptamethine-cyanine dyes and related heptamethine cyanine dyes unsubstituted on the vinyl chain were synthesized by condensation of 2,3,3-trimethyl indolenium salts with reactive intermediates, 2-chloro-formyl-3-hydroxy-methylenecyclohexene or N-[5-(phenylamino)-2,4phentadienylidene] aniline monohydro-chloride. The structures of the dyes were characterized by virtue of 1 H-NMR, 13 C-NMR, IR, MS, etc. The reaction conditions and physicochemical properties of the dyes were extensively explored with classical photo-physical techniques

EP1112254A2 - Cyanine dyes and synthesis methods

Two new crescent-shaped unsymmetrical cyanine dyes have been synthesised and their interactions with DNA have been investigated by different spectroscopic methods. These dyes are analogues to a minor groove binding unsymmetrical cyanine dye, BEBO, recently reported by us. In this dye, the structure of the known intercalating cyanine dye BO was extended with a benzothiazole substituent. To investigate how the identity of the extending heterocycle affects the binding to DNA, the new dyes BETO and BOXTO have a benzothiazole group and a benzoxazole moiety, respectively. Whereas BEBO showed a heterogeneous binding to calf thymus DNA, linear and circular dichroism studies of BOXTO indicate a high preference for minor groove binding. BETO also binds in the minor groove to mixed sequence DNA but has a contribution of non-ordered and non-emissive species present. A non-intercalative binding mode of the new dyes, as well as for BEBO, is further supported by electrophoresis unwinding assays. These dyes, having comparable spectral properties as the intercalating cyanine dyes, but bind in the minor groove instead, might be useful complements for staining of DNA. In particular, the benzoxazole substituted dye BOXTO has attractive fluorescence properties with a quantum yield of 0.52 when bound to mixed sequence DNA and a 300-fold increase in fluorescence intensity upon binding.

The heterogeneous binding of BEBO to mixed sequence DNA prompted us to search for derivatives with a higher preference for the minor groove, and possibly with improved fluorescence enhancement upon DNA binding. The introduction of an extending benzothiazole group in BEBO clearly induced a change in binding mode from intercalation towards minor groove binding. To investigate how the nature of the extending heterocycle affects the binding to DNA, we set out to prepare dyes with benzoxazole (BOXTO) and benzothiazole extensions (BETO) (Fig. ). In contrast to the previous synthetic route towards BEBO, a new strategy was developed that facilitates the preparation of dyes with different extending heterocycles. As judged from the linear and circular dichroism studies, the benzoxazole derivative BOXTO exhibited straightforward minor groove binding both to poly(dA-dT)2 and calf thymus DNA (ctDNA), whereas the benzothiazole derivative BETO showed a more heterogeneous binding to the latter DNA, also with a greater tendency for aggregation. Herein we present the synthesis and DNA-binding studies of these new unsymmetrical cyanine dyes. In an accompanying paper, we present a study of the dissociation of these dyes from DNA under conditions typical for biotechnical application ().

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