Antimicrobial Finish of Polyethersulfone Membranes: Sticking Photosensitizers‐Like Marine Mussels Would Do

Abstract

Biofouling is one of the most serious problems in membrane filtration systems for water treatment. An easily applicable antimicrobial finish of polyethersulfone (PES) filter membranes is shown by derivatizing an approved chlorin photosensitizer drug with adhesive ortho‐catechol functionalities as known from l‐3,4‐dihydroxyphenylalanin (Dopa) residues of marine mussel glues. The chemical structure of the second‐generation photosensitizer 5,10,15,20‐tetrakis(3‐hydroxyphenyl)chlorin (m‐THPC) is modified by 2‐iodoxybenzoic acid (IBX) oxidation, transforming the peripheric meta‐phenols of m‐THPC into ortho‐catechols, and thus improving the adsorption properties of m‐THPC derivatives onto PES material. Stable coatings are formed that preserve chlorin's capability to generate singlet oxygen under visible light illumination. The modification of one or two phenol groups out of the four m‐THPC substituents leads to an optimum in the generation of active singlet oxygen, and thus the finish significantly reduces the bacterial growth of gram‐negative Escherichia coli and gram‐positive Micrococcus luteus on the PES membranes.

Trendbericht: Makromolekulare Chemie 2023

“…42) Ebenfalls antimikrobielle Eigenschaften wiesen die Polyethersulfonmembranen auf, die Börner und Mitarbeitende entworfen und mit Photosensibilisatoren ausgerüstet hatten. 43) Fortschritte in der Synthese biomedizinisch wirksamer Makromoleküle erzielten Hartmann, Snyder und Hoffmann: Ihnen gelang die Festphasensynthese von sulfatierten Glykomakromolekülen als Analoga für biologisch aktive sulfatierte Glykosaminoglykane. 44) Ebenfalls auf der Festphase synthetisierten Delbianco und Mitarbeitende sulfatierte Oligosaccharide.…”

Organic transformation of lignin into mussel-inspired glues: next-generation 2K adhesive for setting corals under saltwater

“…83,84 The remarkably versatile and reversible interaction capabilities of L-DOPA residues lead to a rich class of biomimetic catechol-containing peptides and polymers that demonstrate exciting underwater adhesive properties. 71,74,[85][86][87][88] Recently, a new class of mussel glue-inspired adhesives was fabricated by exploiting the biogenic cystenyldopa connectivity, originating from a thiol-quinone Michael-type addition. 89 β-Thiols derived from cysteine residues were proven to add rapidly and cleanly to oxidized L-DOPA residues in the quinone form.…”