Here aqueous solubilization of hydrophobic tetrapyrrole macrocycles by attachment to an amphiphilic single-chain nanoparticle (SCNP)

Liu, Rui; Liu, Sijia; Hu, Gongfang; Lindsey, Jonathan S.

doi:10.1039/d0nj04413j

Here aqueous solubilization of hydrophobic tetrapyrrole macrocycles by attachment to an amphiphilic single-chain nanoparticle (SCNP)

Journal Article · Wed Nov 25 00:00:00 EST 2020 · New Journal of Chemistry

DOI:https://doi.org/10.1039/d0nj04413j· OSTI ID:1850693

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North Carolina State Univ., Raleigh, NC (United States); OSTI
North Carolina State Univ., Raleigh, NC (United States)

Solubilization of hydrophobic tetrapyrrole macrocycles and other fluorophores in aqueous solution has been achieved by covalent attachment to the terminus of an amphiphilic polymer, thereby affording a single-fluorophore–single-chain nanoparticle (SCNP). The polymer is a heterotelechelic random polyacrylate/polyacrylamide copolymer bearing hydrophobic and hydrophilic pendant groups. The polymer has a folded unimeric morphology (~13 nm hydrodynamic diameter) in 1 M NaCl aqueous solution as indicated by dynamic light-scattering spectroscopy. Five hydrophobic organic fluorophores (coumarin, perylene, two chlorins, one phthalocyanine) have been synthesized with a conjugatable tether. Covalent conjugation of the fluorophore–maleimide to the polymer terminus via thiol–maleimide reaction was carried out in DMF. The resulting fluorophore–SCNP in 1 M NaCl aqueous solution exhibited retained spectral features and fluorescence quantum yield comparable to those of the respective hydrophobic benchmark in toluene. This single-fluorophore–single-polymer strategy simplifies the challenging and often idiosyncratic syntheses of water-soluble tetrapyrrole macrocycles by using the polymer as a general aqueous solubilization package, and in so doing opens up opportunities for the application of hydrophobic fluorophores in the life sciences.

View Accepted Manuscript (DOE)

Research Organization:: Washington Univ., St. Louis, MO (United States)

Sponsoring Organization:: National Institute of General Medical Sciences (NIGMS); Photosynthetic Antenna Research Center (PARC); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001035

OSTI ID:: 1850693

Alternate ID(s):: OSTI ID: 1734809

Journal Information:: New Journal of Chemistry, Journal Name: New Journal of Chemistry Journal Issue: 48 Vol. 44; ISSN 1144-0546

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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