2016
DOI: 10.1039/c6nj01155a
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Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, near-infrared-emitting bacteriochlorins

Abstract: Synthetic bacteriochlorins absorb in the near-infrared (NIR) region and are versatile analogues of natural bacteriochlorophylls. The utilization of these chromophores in energy sciences and photomedicine requires the ability to tailor their physicochemical properties, including the incorporation of units to impart water solubility. Herein, we report the synthesis, from two common bacteriochlorin building blocks, of five wavelength-tunable, bioconjugatable and water-soluble bacteriochlorins along with two non-b… Show more

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Cited by 16 publications
(29 citation statements)
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“…Unwanted reactivity to form oligomeric species is also supressed by using heterobifunctional PEG chains, in which one end of the PEG chain often has a methyl cap. PEGylated porphyrins are also much more amenable to traditional aqueous work-up conditions, as they may partition favorably in organic solvents such as CH2Cl2 and EtOAc [127,128]. Often times PEGylated porphyrins can be purified by normal silica-gel chromatography using polar solvents [14,[129][130][131].…”
Section: Pegylated Porphyrinsmentioning
confidence: 99%
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“…Unwanted reactivity to form oligomeric species is also supressed by using heterobifunctional PEG chains, in which one end of the PEG chain often has a methyl cap. PEGylated porphyrins are also much more amenable to traditional aqueous work-up conditions, as they may partition favorably in organic solvents such as CH2Cl2 and EtOAc [127,128]. Often times PEGylated porphyrins can be purified by normal silica-gel chromatography using polar solvents [14,[129][130][131].…”
Section: Pegylated Porphyrinsmentioning
confidence: 99%
“…Another representative example for the introduction of PEG groups via Suzuki coupling of dibromobacteriochlorin 19 with a Boc-protected amine-derivatized boronic ester, followed by Bocdeprotection under standard conditions, afforded diaryl bacteriochlorin 175 carrying two amine groups. The amines were PEGylated by amide formation with a PEG-NHS ester to afford bacteriochlorin 176 (Scheme 54) [127]. Derivatives bearing bioconjugtable tethers (177) and (178) were also prepared using a regioselective meso-bromination strategy, followed by similar coupling sequences [127].…”
Section: Porphyrins Pegylated At Their β-Positionsmentioning
confidence: 99%
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