Boronic acids for affinity chromatography: Spectral methods for determinations of ionization and diol-binding constants

Soundararajan, Soundaramani; Badawi, M. M.; Kohlrust, Cathy Montaño; Hageman, James H.

doi:10.1016/0003-2697(89)90367-9

Cited by 114 publications

(55 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The boronic acid group has been long known to have high affinity for diol-containing compounds such as carbohydrates [ 19 -21 ], where the strong complexation has been used for the construction of carbohydrate sensors [ 22 -29 ], transporters [ 30 ], and chromatographic materials [ 31 ]. Naturally, boronic acid compounds have been considered as a chelating group for the synthesis of glucose sensors [ 32 -39 ], where we note the work of Shinkai [ 32 , 33 ], Norrild [ 34 ], Lakowicz [ 35 -39 ] and Drueckhammer [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescence sensors for monosaccharides based on the 6-methylquinolinium nucleus and boronic acid moiety: potential application to ophthalmic diagnostics

Badugu

Lakowicz

Geddes

2005

Talanta

View full text Add to dashboard Cite

Continuous monitoring of glucose levels in human physiology is important for the long-term management of diabetes. New signaling methods/probes may provide an improved technology to monitor glucose and other physiologically important analytes. The glucose sensing probes, BMQBAs, fabricated using the 6-methylquinolinium moiety as a fluorescent indicator, and boronic acid as a chelating group, may have versatile applications in glucose sensing because of their unique properties. In this paper we discuss the design logic, synthesis, characterization and spectral properties of three new isomeric glucose sensors (BMQBAs), and a control compound (BMQ) in the presence and absence of sugars. The sensing ability of the new probes is based on a charge neutralization and stabilization mechanism upon sugar binding. The new probes have attractive fluorescence quantum yields, are highly water-soluble, and have spectral characteristics compatible with cheap and portable LEDs and LDs. One of the probes, o-BMQBA, has a sugar bound pK a of 6.1, and a dissociation constant K D of 100 mM glucose. These probes have been designed specifically to respond to tear glucose in a contact lens polymer for ophthalmic glucose monitoring, where the reduced sugar bound pK a affords for sensing, in a lens environment that we have previously shown to be mildly acidic.

show abstract

Section: Introductionmentioning

confidence: 99%

Fluorescence sensors for monosaccharides based on the 6-methylquinolinium nucleus and boronic acid moiety: potential application to ophthalmic diagnostics

Badugu

Lakowicz

Geddes

2005

Talanta

View full text Add to dashboard Cite

show abstract

“…The affinity of boronic acid for diols is well known [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27], hence for any fluoride sensor based on the boronic acid moiety, it is important to characterize the monosaccharide response. Subsequently, we tested the response of BAQBAs towards both glucose and fructose.…”

Section: Resultsmentioning

confidence: 99%

“…Fluoride can be accurately determined using fluoride-ion selective electrodes [8], spectrophotometry [9], gas chromatography [10] and even colorimetrically using boronic acid chemistry [11,12], although such systems are poisoned by the presence of sugars such as by glucose or fructose. It is due to the well-known high affinity between diol containing compounds and the boronic acid moiety that has lead to the development of carbohydrate sensors [13][14][15][16][17][18][19] chromatographic materials [20] and many glucose sensors [21][22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Wavelength–Ratiometric Probes for the Selective Detection of Fluoride Based on the 6-Aminoquinolinium Nucleus and Boronic Acid Moiety

Badugu

Lakowicz

Geddes

2004

Journal of Fluorescence

View full text Add to dashboard Cite

Herein we report a set of new water-soluble fluorescent probes (N -boronobenzyl-6-aminoquinolinium bromides, BAQBAs) sensitive to aqueous fluoride. These probes shows spectral shifts and intensity changes in the presence of fluoride, in a wavelength ratiometric and colorimetric manner, enabling the detection of fluoride concentrations at visible wavelengths, in the concentration range ≈1-300 mM. Although the sensing mechanism is different for fluoride as compared to the other halides, we have tested the utility of these probes towards the other halides, and the results reveal that the BAQBAs are in fact potential candidates towards the sensing of the all the halides, but in different concentration ranges. As the probes are based on the boronic acid moiety, which is a well-known fluoride and sugar chelator group, we have investigated the response of sugars (such as glucose and fructose, which are present in biological fluids and foodstuffs) as interferences in fluoride detection using these probes. Interestingly, the BAQBAs show a suppressed sugar response potentially allowing for the predominant fluoride sensitivity. In addition to physiological sugars, we also have assessed the response of aqueous halides as potential interferents, or indeed analytes to be sensed, and show that the new boronic acid containing probes respond well to aqueous fluoride in the presence of a high background of other species, such as in a biological cocktail of 50 mM Glucose, 50 mM aqueous Chloride and 5 mM Fructose.

show abstract

“…Immobilized phenylboronic acid has been utilized selectively to retain carbohydrates, catecholamines, prostaglandins, ribonucleosides, and steroids [18][19][20]. Boronic acid can form reversible bonds with 1,2-or 1,3-diols to generate five or six membered cyclic complexes under mild conditions [21,22]. Immobilized boronic acid derivatives have been reported to form reversible complexes with diol-containing compounds such as nucleotides [23] nucleosides [24], nucleic acids [25] and carbohydrates [26].…”

Section: Introductionmentioning

confidence: 99%

Sequential affinity purification of peroxidase tagged bispecific anti-SARS-CoV antibodies on phenylboronic acid agarose

Bhatnagar

Das

Suresh

2008

Journal of Chromatography B

View full text Add to dashboard Cite

Hybrid hybridomas (quadromas) are derived by fusing at least two hybridomas, each producing a different antibody of predefined specificity. The resulting cell secretes not only the immunoglobulins of both parents but also hybrid molecules manifesting the binding characteristics of the individual fusion partners. Purification of the desired bispecific immunoprobe with high specific activity from a mixture of bispecific and monospecific monoclonal antibodies requires special strategies. Using a dual, sequential affinity chromatography (Protein-G chromatography followed by maminophenyleboronic acid agarose column), we have purified bispecific monoclonal antibodies (BsMAb) as a preformed HRPO (Horseradish Peroxidase) complex (BsMAb-HRPO). The quadroma culture supernatant was initially processed on a Protein-G column to isolate all the species of immunoglobulins. This pre-enriched fraction was subsequently passed through the aminophenyleboronic acid column super saturated with HRPO. The column matrix has the ability to bind to proteins such as HRPO with vicinal diols. The enzyme loaded column captures the desired bispecific anti-SARS-CoV × anti-HRPO species with the elimination of the monospecific anti-SARS-CoV MAb to result in a high specific activity diagnostic probe. The presence of anti-HRPO MAb is an acceptable impurity as it will not bind to the target SARS-CoV NP antigen and will get washed out during the ELISA procedure.

show abstract

Boronic acids for affinity chromatography: Spectral methods for determinations of ionization and diol-binding constants

Cited by 114 publications

References 20 publications

Fluorescence sensors for monosaccharides based on the 6-methylquinolinium nucleus and boronic acid moiety: potential application to ophthalmic diagnostics

Fluorescence sensors for monosaccharides based on the 6-methylquinolinium nucleus and boronic acid moiety: potential application to ophthalmic diagnostics

Wavelength–Ratiometric Probes for the Selective Detection of Fluoride Based on the 6-Aminoquinolinium Nucleus and Boronic Acid Moiety

Sequential affinity purification of peroxidase tagged bispecific anti-SARS-CoV antibodies on phenylboronic acid agarose

Contact Info

Product

Resources

About