4′-[Aminomethyl]fluorescein and its N-alkyl derivatives: Useful reagents in immunodiagnostic techniques

Shipchandler, M. T.; Fino, James R.; Klein, Lavy; Kirkemo, C.L.

doi:10.1016/0003-2697(87)90013-3

Cited by 23 publications

(10 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These derivatives allow for conjugation of ligands through the 5-or 6-position of the phenyl ring of fluorescein. Additionally, 4′-(aminomethyl)fluorescein has been utilized for the preparation of tracers used in commercially available immunoassays (10,11). This fluorescein derivative allows for conjugation through the xanthinyl ring of fluorescein.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of 3‘-O-(Carboxyalkyl)fluorescein Labels

1999

View full text Add to dashboard Cite

A general and versatile method is described for the synthesis of fluorescent labels. Coupling of the 3'-phenol of fluorescein methyl ester with hydroxyalkyl benzyl esters, followed by benzyl ester hydrolysis, provided a series of fluorescein carboxyalkyl ethers. Use of the Mitsunobu reaction allowed for the introduction of linkers of different lengths onto the 3'-phenol of fluorescein. Chemoenzymatic benzyl ester hydrolysis was achieved with LPL-80 lipase, providing pH-independent labels useful for the preparation of fluorescent conjugates.

show abstract

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of 3‘-O-(Carboxyalkyl)fluorescein Labels

1999

View full text Add to dashboard Cite

show abstract

“…Synthesis of Fluorescently Labeled Solanidine (AMF-SOL) (Figure 1). Solanidine hemisuccinate was synthesized according to the method of Plhak and Spoms (1992) and coupled to 4'-(aminomethyl)fluorescein dihydrochloride (4'-AMF) using the active ester method of Shipchandler et al (1987). Solanidine hemisuccinate (21.1 mg) was reacted with 4.18 mg of N-hydroxysuccinimide and 6.24 mg of 1,3-dicyclohexylcarbodiimide in 625 µ1> of dry NN-dimethylformamide (DMF) at room temperature for 30 h. Urea formed during the reaction was removed by filtration.…”

Section: Methodsmentioning

confidence: 99%

Fluorescence Polarization Immunoassays for Potato Glycoalkaloids

Thomson¹,

Sporns²

1995

J. Agric. Food Chem.

View full text Add to dashboard Cite

Fluorescence polarization immunoassays (FPIAs) were developed for potato glycoalkaloids (GAs) using a polyclonal antiserum and a monoclonal antibody (MAb). Fluorescently labeled solanidine (AMF-SOL) was synthesized by coupling 4'-(aminomethyl)fluorescein (4'-AMF) to the hemisuccinate derivative of solanidine using an active ester method. Both polyclonal antibody (PAb) and MAb could quantify the major potato GAs in the 20-100 nM range; however, the affinities of PAb and MAb differed slightly among the individual GAs. PAb displayed the greatest affinity for a-chaconine, while MAb was more sensitive to changes in -solanine levels. Affinity constants (ifaff) of PAb and MAb for AMF-SOL were estimated at 4.2 x 108 and 4.7 x 107 M-1, respectively. Potato samples containing low, medium, and high levels of GAs were successfully analyzed by the PAb FPIA. Equilibrium in the FPIA reaction was reached within 1-2 min, and standard curves were stable for at least 14 days.

show abstract

“…O O COOH HO Since its simple derivatives had proves to be among the most versatile of chromophores used as fluorescence probes, more and more FL derivatives had been synthesized [19,20]. The most commonly used derivatives include the carboxy-fluoresceins, the aminofluoresceins, the fluoresceins isothiocyanates, and the aminomethylfluoresceins.…”

Section: Introductionmentioning

confidence: 99%