Neopentyl 3-Triflyloxypropanesulfonate. A Reactive Sulfopropylation Reagent for the Preparation of Chemiluminescent Labels

Adamczyk, Maciej; Chen, Yon-Yih; Mattingly, Phillip G.; Pan, You; Rege, Sushil

doi:10.1021/jo980047r

Cited by 40 publications

(22 citation statements)

References 20 publications

(21 reference statements)

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“…(10). Such a compound has been shown to display some features such as improved solubility, stability and light emission which may affect the performance.…”

Section: Discussionmentioning

confidence: 99%

A New Modular Chemiluminescence Immunoassay Analyser Evaluated

Ognibene¹,

Drake²,

Jeng³

et al. 2000

CCLM

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Thyrotropin (TSH), free thyroxine (fT4) and testosterone assays have been used as a probe to evaluate the performances of a new modular chemiluminescence (CL) immunoassay analyser, the Abbott Architect 2000. The evaluation was run in parallel on other systems that use CL as the detection reaction: DPC Immulite, Chiron Diagnostics ACS-180 and ACS Centaur (TSH functional sensitivity only). TSH functional sensitivity was 0.0012, 0.009, 0.033 and 0.039 mU/I for the Architect, Immulite, ACS Centaur and ACS-180, respectively. Testosterone functional sensitivity was 0.38, 3.7 and 2.0 nmol/l for Architect, Immulite and ACS-180, respectively. Good correlation was obtained between the ACS-180 and Architect for all assays. The Immulite correlation did not agree well with the Architect or ACS-180 for fT4 and testosterone but was in good agreement for TSH. Regarding fT4 and testosterone, equilibrium dialysis and isotopic dilution gas-chromatography mass-spectrometry (GC-MS) respectively were used as reference methods. For both within- and between-run precision, the Architect showed the best reproducibility for all three analytes (CV < 6%).

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“…(10). Such a compound has been shown to display some features such as improved solubility, stability and light emission which may affect the performance.…”

Section: Discussionmentioning

confidence: 99%

A New Modular Chemiluminescence Immunoassay Analyser Evaluated

Ognibene¹,

Drake²,

Jeng³

et al. 2000

CCLM

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“…The acridinium-9-carboxamide label 1 (12,13) and O-(6-fluoresceinylmethyl)hydroxylamine 2 (6-OFMHA) (14,15) were prepared as previously described. 5-(Biotinamido)pentylamine 3 was obtained from Pierce Chemical Co. UVvis spectroscopy was performed on a Beckman DU 640 spectrophotometer (Fullerton, CA).…”

Section: Methodsmentioning

confidence: 99%

Surface Plasmon Resonance (SPR) as a Tool for Antibody Conjugate Analysis

et al. 1999

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Surface plasmon resonance (SPR) analysis was used to assess the immunoreactivity of anti-biotin (4) and anti-fluorescein (5) monoclonal antibody after conjugation with the N-hydroxysuccinimide ester of acridinium-9-carboxamide 1. Only minor changes in the apparent equilibrium dissociation constants of the antibody conjugates for their ligands resulted from the conjugation process. However, comparison of the initial binding rate of the conjugates with their ligands with those of the unmodified antibodies over a range of concentrations showed that the antibody conjugates were partially inactivated. The anti-fluorescein conjugates retained at least 90% of their immunoreactivity over the range of modification tested, while anti-biotin conjugates showed a progressive loss of reactivity with increased substitution by the label.

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“…Typical reported yields were B15% (3Á14%) using these powerful alkylating reagents and, moreover, these N-alkylation reactions were conducted in toxic solvents such as nitrobenzene or 1,2-dichloroethane. Similarly, Adamczyk [37] and co-workers have reported that introduction of the N-sulfopropyl group in acridine N-sulfonylcarboxamides with poor reactivity can be performed using the reagent neopentyl 3-trifloxypropane sulfonate. However, N-alkylation using even this strong alkylating reagent required 7 days to afford 34% conversion to product.…”

Section: Resultsmentioning

confidence: 99%

A green synthesis of chemiluminescent N-sulfopropyl acridinium esters in ionic liquids without using the carcinogen 1,3-propane sultone

Natrajan

Wen

2013

Green Chemistry Letters and Reviews

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Chemiluminescent acridinium dimethylphenyl esters containing hydrophilic N-sulfopropyl groups in the acridinium ring are used as labels in automated immunoassays for clinical diagnostics. Introduction of the N-sulfopropyl group in these labels is normally accomplished by N-alkylation of the corresponding, nonchemiluminescent acridine ester precursors with the toxic carcinogen 1,3-propane sultone. In the current study, we report that sodium 3-bromopropane sulfonate in ionic liquids (ILs) is a benign alternative to 1,3-propane sultone for introducing the N-sulfopropyl group in chemiluminescent acridinium ester labels. The sultone reagent can be eliminated in the synthesis of N-sulfopropyl acridinium dimethylphenyl ester labels by taking advantage of the increased reactivity of acridan esters toward nontoxic sodium 3-bromopropane sulfonate in [BMIM] [BF 4 ]. Sodium 3-bromopropane sulfonate in ILs is also potentially a nontoxic alternative to 1,3-propane sultone for introducing the water-soluble, three-carbon sulfobetaine moiety in other molecules as well.

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Neopentyl 3-Triflyloxypropanesulfonate. A Reactive Sulfopropylation Reagent for the Preparation of Chemiluminescent Labels

Cited by 40 publications

References 20 publications

A New Modular Chemiluminescence Immunoassay Analyser Evaluated

A New Modular Chemiluminescence Immunoassay Analyser Evaluated

Surface Plasmon Resonance (SPR) as a Tool for Antibody Conjugate Analysis

A green synthesis of chemiluminescent N-sulfopropyl acridinium esters in ionic liquids without using the carcinogen 1,3-propane sultone

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