Oral toxicity of the cyclic polyethers—12-crown-4, 15-crown-5, and 18-crown-6—in mice

Hendrixson, Richard R.; Mack, Mark P.; Palmer, Richard A.; Ottolenghi, Athos; Ghirardelli, Robert G.

doi:10.1016/0041-008x(78)90188-6

Cited by 57 publications

(31 citation statements)

References 7 publications

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“…On the toxicity of crown ethers, the acute LD50 (lethal dose, 50 percent kill) values in mice of 12-crown-4, 15-crown-5, and 18-crown-6 are 3,150 mg/kg, 1,020 mg/kg, and 7,100 mg/kg respectively 46) .…”

Section: Stability Of Apo-na and Biological Safety Of Crown Ethersmentioning

confidence: 99%

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

2010

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This paper reviews our recent studies on radical photopolymerization initiators, which are used in the design of light-curing dental adhesives and resin composites, by collating information of related studies from original scientific papers, reviews, and patent literature. The photopolymerization reactivities of acylphosphine oxide (APO) and bisacylphosphine oxide (BAPO) derivatives, and D,L-camphorquinone (CQ)/tertiary amine were investigated, and no significant differences in degree of conversion (DC) were found between BAPO and CQ/amine system (p>0.05). In addition, a novel 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carbonyldiphenyl phosphine oxide (DOHC-DPPO=CQ-APO) was synthesized and its ultraviolet and visible (UV-VIS) spectral behavior was investigated. CQ-APO possessed two maximum absorption wavelengths (λmax) at 350-500 nm [372 nm (from APO group) and 475 nm (from CQ moiety)], and CQ-APO-containing resins exhibited good photopolymerization reactivity, excellent color tone, relaxed operation time, and high mechanical strength. It was also found that a newly synthesized, water-soluble photoinitiator (APO-Na) improved adhesion to ground dentin.

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Section: Stability Of Apo-na and Biological Safety Of Crown Ethersmentioning

confidence: 99%

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

2010

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“…Based on the biological safety data and information of crown ethers presented in published literature, crown ethers were labeled as "harmful or irritant" reagents in Sigma-Aldrich reagents catalog (2006-2007 catalog, Sigma-Aldrich Corp., Missouri, USA). On the toxicity of crown ethers, the acute LD50 (lethal dose, 50 percent kill) values in mice of 12-crown-4, 15-crown-5, and 18-crown-6are3115mg/kg,1020mg/kg,and710mg/kg respectively 32) . Among these three crown ethers studiedbyHendrixsonet al 32) ,itwasfoundthatwith increasingcrownsize,theseverityofsymptoms(body tremors,respiratoryimpairment)decreasedwhilethe length of time to onset of symptoms and to death increased.Ithasbeenreportedthatasublethaldose of 18-crown-6 resulted in tremors, salivation, and hind leg paralysis in dogs 33) , rats, and rabbits 34) .…”

Section: Biological Safety Of Crown Ethersmentioning

confidence: 99%

“…On the toxicity of crown ethers, the acute LD50 (lethal dose, 50 percent kill) values in mice of 12-crown-4, 15-crown-5, and 18-crown-6are3115mg/kg,1020mg/kg,and710mg/kg respectively 32) . Among these three crown ethers studiedbyHendrixsonet al 32) ,itwasfoundthatwith increasingcrownsize,theseverityofsymptoms(body tremors,respiratoryimpairment)decreasedwhilethe length of time to onset of symptoms and to death increased.Ithasbeenreportedthatasublethaldose of 18-crown-6 resulted in tremors, salivation, and hind leg paralysis in dogs 33) , rats, and rabbits 34) . However,thesesymptomswerereversibleandwould disappear after discontinuance of exposure to these compounds 34) .…”

Section: Biological Safety Of Crown Ethersmentioning

confidence: 99%

Design of a new dental adhesive-Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

et al. 2009

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Thebehaviorofwater-solublephotoinitiatorswithcrownethersindentaladhesivesisunknown.Thisstudyinvestigatedthe effectofsodiumacylphosphineoxide(APO-Na)withcrownetherinahydrophobicadhesiveonadhesiontoteeth.Sodium 2,4,6-trimethylbenzoyl-phenylphosphine oxide (TMPO-Na = APO-Na) was synthesized in 67.1% yield and identified by 1 H NMR. APO-Na was dissolved in hydrophobic resins in the presence of a crown ether (ionophore effect). Thirty kinds of experimentalsingle-stepadhesivescomprisingAPO-Na,CE,Bis-GMA,6-methacryloyloxyhexylphosphonoacetate(6-MHPA), and4-methacryloyloxyethyltrimelliticacid(4-MET)weretherebyprepared.Shearbondstrengthtounetchedgroundteeth wasmeasuredatacrossheadspeedof1.0mm/min,andthedatawereanalyzedbyANOVA.Theshearbondstrengthresults of bonding resins containing APO-Na with 18-crown-6-ether (CE-6) were significantly higher than that without CE-6 (control) (p<0.05).Higherbondstrengthvalues[forenamel:BR24at19.3(3.2)MPa;fordentin:BR29at20.2(4.7)MPa]wereachieved with the adhesives containing APO-Na, CE-6, 6-MHPA, and 4-MET. Therefore, it was found that APO-Na with CE-6 contributed to the efficient bonding performance of single-step adhesive to teeth. However, in view of the biosafety hazard posedbycrownethers,thesearchisstillonforreagentsthatarebiologicallysaferthancrownethers-butwithionophor effects-tobeusedindentaladhesives.

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“…The acute LD50 (lethal dose, 50 percent kill) values in mice of 12-crown-4, 15-crown-5, and 18-crown-6 are 3,115 mg/kg, 1,020 mg/ kg, and 710 mg/kg respectively 46) . In view of the biosafety hazards posed by crown ethers, the search is still on for reagents that are biologically safer than crown ethersbut with ionophore effect-to be used in dental adhesives.…”

Section: Bonding Mechanism Of Apo-na-containing Adhesive To Dentin Anmentioning

confidence: 99%

A review of the developments of self-etching primers and adhesives —Effects of acidic adhesive monomers and polymerization initiators on bonding to ground, smear layer-covered teeth

2011

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This paper reviews the developments of self-etching primers and adhesives, with a special focus on the effect of acidic adhesive monomers and polymerization initiators on bonding to ground, smear layer-covered teeth. Ionized acidic adhesive monomers chemically interact with tooth substrates and facilitate good bonding to ground dentin. Polymerization initiators in self-etching primers further promote effective bonding to ground dentin. To promote bonding to both dentin and enamel, phosphonic acid monomers such as 6-methacryloyloxyhexyl phosphonoacetate (6-MHPA) were developed. These novel adhesive monomers also have a water-soluble nature and are hence endowed with sufficient demineralization capability. A new single-bottle, self-etching, 2-hydroxyethyl methacrylate (HEMA)-free adhesive comprising 6-MHPA and 4-acryloyloxyethoxycarbonylphthalic acid (4-AET) was developed. This novel adhesive enabled strong adhesion to both ground enamel and dentin, but its formulation stability was influenced by pH value of the adhesive. To develop hydrolytically stable, single-bottle, self-etching adhesives, hydrolytically stable, radical-polymerizable acidic monomers with amide or ether linkages have been developed.

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Oral toxicity of the cyclic polyethers—12-crown-4, 15-crown-5, and 18-crown-6—in mice

Cited by 57 publications

References 7 publications

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

Design of a new dental adhesive-Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

A review of the developments of self-etching primers and adhesives —Effects of acidic adhesive monomers and polymerization initiators on bonding to ground, smear layer-covered teeth

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