Sensing of antipyretic carboxylates by simple chromogenic calix[4]pyrroles.
We present a simple, two- or three-step method for the synthesis of chromogenic octamethylcalix[4]pyrrole-based (OMCP) sensors for anions. Electrophilic aromatic substitution allows for converting the pyrrole moieties of OMCP into a dye. The formation of a sensor-anion complex results in partial charge transfer and a dramatic change in color. The absorption (UV-vis) and NMR titration experiments show that the chromogenic OMCPs sense anions administered as aqueous solutions, even at high ionic strength ( approximately 0.1 M NaCl), while displaying selectivity for pyrophosphate and carboxylate anions. The experiments with polyurethane sensor films show a strong response for aqueous carboxylates, such as antipyretics naproxen approximately ibuprofen > salicylate, without being biased by bicarbonate or carboxy termini of blood plasma proteins.
Nishiyabu
Ryuhei
R
Department of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Bowling Green, OH 43403, USA.
Anzenbacher
Pavel
P
D018712:Analgesics, Non-Narcotic / Q000032:analysis* / Q000097:blood / Q000737:chemistry; D000818:Animals; D000838:Anions / Q000032:analysis / Q000737:chemistry; D015374:Biosensing Techniques / Q000379:methods; D001798:Blood Proteins / Q000032:analysis; D047250:Calixarenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000032:analysis* / Q000097:blood / Q000737:chemistry; D006801:Humans; D007052:Ibuprofen / Q000032:analysis / Q000097:blood; D009288:Naproxen / Q000032:analysis / Q000097:blood; D019906:Nuclear Magnetic Resonance, Biomolecular; D011166:Porphyrins / Q000737:chemistry*; D012459:Salicylates / Q000032:analysis / Q000097:blood; D012710:Serum Albumin, Bovine / Q000032:analysis; D013053:Spectrophotometry / Q000379:methods
D018712:Analgesics, Non-Narcotic; D000838:Anions; D001798:Blood Proteins; D002264:Carboxylic Acids; D011166:Porphyrins; D012459:Salicylates; C469811:calix(4)pyrrole; D047250:Calixarenes; D012710:Serum Albumin, Bovine; D009288:Naproxen; D007052:Ibuprofen