Anion sensors based on β,β′-disubstituted porphyrin derivatives

Starnes, Stephen D.; Arungundram, Sailaja; Saunders, Colene H.

doi:10.1016/s0040-4039(02)01828-2

Cited by 81 publications

(34 citation statements)

References 38 publications

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“…829 In this case, UV-Vis-based binding studies carried out in dichloromethane with TBA anion salts led to the conclusion that the anion selectivity of receptor 818 correlated with the basicity of the analytes. The strongest interactions were observed for fluoride, followed by dihydrogenphosphate ( K = 7 × 10 -4 M -1 ).…”

Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 93%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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Section: Major Phosphate-binding Functionalitiesmentioning

confidence: 93%

Artificial Receptors for the Recognition of Phosphorylated Molecules

et al. 2011

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“…1,10-Phenanthroline-5,6-dione (phendione), [31] 4,5-dinitro-1,2-phenylenediamine, 1,2-dinitro-4,5-bis(p-toluenesulfamido)benzene, [32] 1,2-diamino-4,5-bis(p-toluenesulfamido)benzene, [32] 11,12-diaminodipyrido[3,2-a:2',3'-c]phenazine (dadppz), 11,12-dinitrodipyrido[3,2-a:2',3'-c]phenazine (dndppz), [(phen) 2 Ru(phendione)]Cl 2 , [5c] Ru(bpy) 2 Cl 2 , [33] Ru(Me 4 phen) 2 Cl 2 , [34] Ru(Ph 2 phen) 2 Cl 2 , [34] [(Ph 2 phen) 2 Ru (phendione)][PF 6 ] 2 , [35] [(phen) 2 Ru(tatpp)Ru(phen) 2 ][PF 6 ] 4 , [16] Ru(Me 4 phen) 2 Cl 2 , Ru(Ph 2 phen) 2 Cl 2 ,[ (Ph 2 phen) 2 Ru(phendione)][PF 6 ] 2 ,[ Ru(Ph 2 phen) 3 ] 1,10-Phenathroline (phen), 4,7-diphenyl-1,10-phenanthroline (Ph 2 phen), 3,4,7,8-tetramethyl-1,10phenanthroline (Me 4 phen), ammonium hexafluorophosphate, N,Ndiethylformamide, ethanol, lithium chloride, chloroform, dimethyl sulfoxide, acetonitrile were purchased from Aldrich and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, DNA Cleavage Activity, Cytotoxicity, Acetylcholinesterase Inhibition, and Acute Murine Toxicity of Redox‐Active Ruthenium(II) Polypyridyl Complexes

et al. 2017

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Four mononuclear [(L-L) Ru(tatpp)] and two dinuclear [(L-L) Ru(tatpp)Ru(L-L) ] ruthenium(II) polypyridyl complexes (RPCs) containing the 9,11,20,22-tetraazatetrapyrido[3,2-a:2',3'-c:3'',2''-l:2''',3'''-n]pentacene (tatpp) ligand were synthesized, in which L-L is a chelating diamine ligand such as 2,2'-bipyridine (bpy), 1,10-phenanthroline (phen), 3,4,7,8-tetramethyl-1,10-phenanthroline (Me phen) or 4,7-diphenyl-1,10-phenanthroline (Ph phen). These Ru-tatpp analogues all undergo reduction reactions with modest reducing agents, such as glutathione (GSH), at pH 7. These, plus several structurally related but non-redox-active RPCs, were screened for DNA cleavage activity, cytotoxicity, acetylcholinesterase (AChE) inhibition, and acute mouse toxicity, and their activities were examined with respect to redox activity and lipophilicity. All of the redox-active RPCs show single-strand DNA cleavage in the presence of GSH, whereas none of the non-redox-active RPCs do. Low-micromolar cytotoxicity (IC ) against malignant H358, CCL228, and MCF7 cultured cell lines was mainly restricted to the redox-active RPCs; however, they were substantially less toxic toward nonmalignant MCF10 cells. The IC values for AChE inhibition in cell-free assays and the acute toxicity of RPCs in mice revealed that whereas most RPCs show potent inhibitory action against AChE (IC values <15 μm), Ru-tatpp complexes as a class are surprisingly well tolerated in animals relative to other RPCs.

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“…More recently, Janout et al have reported bile acid derived molecular umbrellaassisted transport of an oligonucleotide across cholesterol-rich phospholipid bilayers [5]. Porphyrin conjugates are potential supramolecular hosts as revealed by their use in saccharide sensing [6,7,8,9], anion binding [10,11,12], and nucleotide recognition in protic media [13,14]. We have recently reported the synthesis and characterization, as well as nucleotide binding studies, of tetrameric cholic acid-porphyrin conjugates 1-4 ( Figure 1) [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

et al. 2007

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Synthesis and characterization of bile acid-porphyrin conjugates (BAPs) are reported. Binding of saccharides with BAPs in aqueous methanol was studied by monitoring changes in the visible absorption spectral of the porphyrin-moieties. Although these studies clearly showed absorbance changes, suggesting quite high if non-selective binding, the mass spectral studies do not unambiguously support these results.

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Anion sensors based on β,β′-disubstituted porphyrin derivatives

Cited by 81 publications

References 38 publications

Artificial Receptors for the Recognition of Phosphorylated Molecules

Artificial Receptors for the Recognition of Phosphorylated Molecules

Synthesis, DNA Cleavage Activity, Cytotoxicity, Acetylcholinesterase Inhibition, and Acute Murine Toxicity of Redox‐Active Ruthenium(II) Polypyridyl Complexes

Synthesis, Characterization, and Saccharide Binding Studies of Bile Acid − Porphyrin Conjugates

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