Bifunctional reactive pentamethine cyanine dyes for biomedical applications

New unsymmetrical pentamethine cyanine dyes containing two non-equivalent reactive groups selected from carboxyl, amino and hydroxyl in different combinations were synthesized and their spectral properties investigated. Amino and hydroxy groups were used for binding the dyes to the anticancer drug,...

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Bibliographic Details
Published in:Dyes and pigments 2019-03, Vol.162, p.18-25
Main Authors: Rozovsky, Alex, Patsenker, Leonid, Gellerman, Gary
Format: Article
Language:English
Subjects:
Bifunctional dyes
Chlorambucil
Cyanines
Drug delivery monitoring
Fluorescent labels
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Summary:New unsymmetrical pentamethine cyanine dyes containing two non-equivalent reactive groups selected from carboxyl, amino and hydroxyl in different combinations were synthesized and their spectral properties investigated. Amino and hydroxy groups were used for binding the dyes to the anticancer drug, chlorambucil (CLB) via biodegradable amide or ester linker while the second reactive functionality could be utilized for attachment at mild conditions to a targeting carrier such as an antibody or peptide. These conjugates can thereby potentially be suitable for fluorescence-based monitoring of drug delivery. The CLB release profiles triggered by biodegradable linker were investigated in buffer solutions and cell medium using LC-MS and spectrofluorimetric methods. [Display omitted] •New unsymmetrical, bifunctional pentamethine cyanine dyes were synthesized.•These dyes contain carboxyl, amino and hydroxyl groups in different combinations.•Amino and hydroxy groups were bound to anticancer drug, chlorambucil (CLB).•Spectral properties and CLB release profiles of the conjugates were investigated.•These conjugates are suitable for fluorescence-based monitoring of drug delivery.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2018.09.064