Highly-Soluble Cyanine J-aggregates Entrapped by Liposomes for In Vivo Optical Imaging around 930 nm

Theranostics
Dyego MirandaJonathan F Lovell

Abstract

Near infrared (NIR) dyes are useful for in vivo optical imaging. Liposomes have been used extensively for delivery of diverse cargos, including hydrophilic cargos which are passively loaded in the aqueous core. However, most currently available NIR dyes are only slightly soluble in water, making passive entrapment in liposomes challenging for achieving high optical contrast. Methods: We modified a commercially-available NIR dye (IR-820) via one-step Suzuki coupling with dicarboxyphenylboronic acid, generating a disulfonated heptamethine; dicarboxyphenyl cyanine (DCP-Cy). DCP-Cy was loaded in liposomes and used for optical imaging. Results: Owing to increased charge in mildly basic aqueous solution, DCP-Cy had substantially higher water solubility than indocyanine green (by an order of magnitude), resulting in higher NIR absorption. Unexpectedly, DCP-Cy tended to form J-aggregates with pronounced spectral red-shifting to 934 nm (from 789 nm in monomeric form). J-aggregate formation was dependent on salt and DCP-Cy concentration. Dissolved at 20 mg/mL, DCP-Cy J-aggregates could be entrapped in liposomes. Full width at half maximum absorption of the liposome-entrapped dye was just 25 nm. The entrapped DCP-Cy was readily detectable...Continue Reading

Citations

Jun 25, 2019·Biomaterials Science·Dyego MirandaJonathan F Lovell
Apr 24, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Ziling YanZhengqing Guo
Dec 6, 2019·ACS Applied Materials & Interfaces·Behzad ChangalvaieKeith P Johnston

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Methods Mentioned

BETA
NMR
size-exclusion chromatography
membrane filtration
dissection
fluorescence imaging
dynamic light scattering
electron microscopy

Software Mentioned

ImageJ

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