Synthesis and Characterization of Glucosamine-Bound Near-Infrared Probes for Optical Imaging

Liu, Cong; Greenwood, Tiffany R.; Bhujwalla, Zaver M.; Glunde, Kristine

doi:10.1021/ol060783e

Cited by 57 publications

(45 citation statements)

References 27 publications

(29 reference statements)

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“…Therefore, the low increase in fluorescence of the acceptor NIR dyes is most likely caused by the low quantum yield of the NIR-dyes (ϕ=0.04 and 0.02). [16,28] When using these dye pairs, FRET quenching of the Cy5 emission provides the most sensitive way to monitor the complex assembly and/or disassembly. The pH is shown to be of influence on the complex formation between HSA and ICG with an optimum pH ≤ 7 (Fig.…”

Section: Discussionmentioning

confidence: 99%

Targeted non-covalent self-assembled nanoparticles based on human serum albumin

et al. 2012

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Human serum albumin (HSA) is a biological nanocarrier that forms non-covalent complexes with a number of synthetic and biomolecules. Previously we demonstrated radiolabeled HSA-based nanoparticles can form non-covalent complexes with fluorescent cyanine dyes yielding imaging agents for surgical guidance towards tumor draining lymph nodes. Here the self-assembly approach enabled rapid clinical translation. Based on this experience we reasoned it would be interesting to expand this non-covalent technology to a targeted approach. The ability of HSA to form non-covalent self-assembled complexes with peptides via near-infrared (NIR) cyanine dyes was explored. Föster resonance energy transfer (FRET) quenching interactions between HSA-Cy5 and the non-covalently bound fluorescent molecules indocyanine green (ICG), IR783-CO2H and three IR783-labeled targeting peptides were used to monitor complex assembly and disassembly. The host-guest interactions between HSA and IR783-labeled peptides enabled the formation of (bio)nanoparticles that are coated with peptides that may target αvβ3-integrins, the chemokine receptor 4 (CXCR4), and somatostatin receptors. The potential of CXCR4-targeted (bio)nanoparticles in sentinel lymph node procedures is demonstrated. By non-covalently binding NIR-dye labeled peptides to an already clinically approved HSA-scaffold, we have readily formed targeted bionanoparticles.

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Section: Discussionmentioning

confidence: 99%

Targeted non-covalent self-assembled nanoparticles based on human serum albumin

et al. 2012

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“…These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S NR 1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed Alcohol [15][16][17][18] or thiol [19][20][21][22] groups are often employed to replace the chlorine atom at the central ring. The resulting ethers or thioethers unfortunately present relatively low chemical stability limiting their use as fluorescent probes in vivo.…”

Section: Introductionmentioning

confidence: 99%

Combining Aminocyanine Dyes with Polyamide Dendrons: A Promising Strategy for Imaging in the Near‐Infrared Region

Ornelas

Lodescar

Durandin

et al. 2011

Chemistry A European J

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Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct S(NR)1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.

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“…[40] Recent studies have shown that NIR probes conjugated onto glucosamine have selectivity for lysosomes. [41] These NIR fluorescent glucosamine-bound probes demonstrated selective accumulation in lysosomes in human breast cancer tumor xenografts. [40]…”

Section: Optical Imaging Probesmentioning

confidence: 99%