Synthesis of a fluorescent boronic acid which reversibly binds to cell walls and a diboronic acid which agglutinates erythrocytes

Burnett, Thomas J; Peebles, H.C.; Hageman, James H.

doi:10.1016/0006-291x(80)91194-8

Cited by 59 publications

(14 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…An early and initially underappreciated demonstration of the targeting of cell-surface structures was the work of Hageman with fluorescent dansyl boronates shown to associate with Bacillus subtilis. [56] They were also able to show a diboronate could display other lectin like properties such as promoting the agglutination of erythrocytes. Not long after that, Gallop developed a method he defined as "boradaption" using boronates to transfer lipophilic dyes and probes into cells.…”

Section: Boron-cell Surface Interactionsmentioning

confidence: 99%

Boron-Carbohydrate Interactions

Pappin¹,

Kiefel²,

Houston³

2012

Carbohydrates - Comprehensive Studies on Glycobiology and Glycotechnology

View full text Add to dashboard Cite

Section: Boron-cell Surface Interactionsmentioning

confidence: 99%

Boron-Carbohydrate Interactions

Pappin¹,

Kiefel²,

Houston³

2012

Carbohydrates - Comprehensive Studies on Glycobiology and Glycotechnology

View full text Add to dashboard Cite

“…Interestingly, a glycoprotein that cross-reacted with the same antibody used by Bonilla et al (1997) was proposed as a possible adhesion molecule between the plasma membrane and the cell wall (Pont-Lezica et al, 1993). In animal cells, a molecule containing two boronic acid residues [N,N#-bis-3(dihydroxylborylbenzene blood cells in suspension (Burnett et al,1980), suggesting that borate linkages can function in cell-to-cell adhesion.…”

Section: Does Boron Function In Transvacuolar Cytoplasmicmentioning

confidence: 99%

Use of Phenylboronic Acids to Investigate Boron Function in Plants. Possible Role of Boron in Transvacuolar Cytoplasmic Strands and Cell-to-Wall Adhesion

2004

View full text Add to dashboard Cite

The only defined physiological role of boron in plants is as a cross-linking molecule involving reversible covalent bonds with cis-diols on either side of borate. Boronic acids, which form the same reversible bonds with cis-diols but cannot cross-link two molecules, were used to selectively disrupt boron function in plants. In cultured tobacco (Nicotiana tabacum cv BY-2) cells, addition of boronic acids caused the disruption of cytoplasmic strands and cell-to-cell wall detachment. The effect of the boronic acids could be relieved by the addition of boron-complexing sugars and was proportional to the boronic acid-binding strength of the sugar. Experiments with germinating petunia (Petunia hybrida) pollen and boronate-affinity chromatography showed that boronic acids and boron compete for the same binding sites. The boronic acids appear to specifically disrupt or prevent borate-dependent cross-links important for the structural integrity of the cell, including the organization of transvacuolar cytoplasmic strands. Boron likely plays a structural role in the plant cytoskeleton. We conclude that boronic acids can be used to rapidly and reversibly induce boron deficiency-like responses and therefore are useful tools for investigating boron function in plants.Plant biologists have known since 1923 that boron is required for plant growth (Warington, 1923) and yet only recently has a definitive role for boron been identified in plant cell walls (Kobayashi et al., 1996;O'Neill et al., 1996O'Neill et al., , 2001Matoh, 1997;Ishii et al., 1999). A sole role for boron in plant cell walls, however, is inadequate to explain all of the observed effects of boron deficiency seen in plants (Brown et al., 2002). The suggestion that boron plays a broader role in biology is primarily supported by the discovery that boron is essential for animals (Nielsen, 2000), where a pectin-rich cell wall is not present. Experimental data from plants and animals imply that boron may have a critical role in membranes and/or the extracellular matrix (for review, see Blevins and Lukaszewski, 1998;Brown et al., 2002).Current understanding of boron physiology suggests that boron in plants likely functions as a crosslinking molecule (Loomis and Durst, 1992;Brown et al., 2002). Borate can cross-link molecules because it contains two pair of hydroxyl moieties that can form reversible diester bonds with molecules containing cisdiols in a favorable conformation. The importance of borate serving as a cross-linking molecule is highlighted by the discovery of several borate-dependent molecules, including rhamnogalacturonan II (RG-II) in plant cell walls (Ishii and Matsunaga, 1996;Kobayashi et al., 1996;O'Neill et al., 1996;Kaneko et al., 1997;Matoh, 1997), boron-polyhydric alcohol complexes identified from phloem extracts (Hu et al., 1997), a bacterial signaling molecule and its sensor protein (Chen et al., 2002), as well as several antibiotics (Hunt, 2003).Boronates (i.e. boronic acids) are a structurally similar but diverse class of molecules that can form r...

show abstract

“…The other probe Rh-B-PBA is lipophilic and zwitterionic. It is well known that a boronic acid moiety binds glycosylated molecules [13]. Alterations in mucin biochemistry are characterised by the appearance of vicinal hydroxyl groups, which constitute binding sites for Rh-B-PBA.…”

Section: Discussionmentioning

confidence: 99%

“…Rh-B-L can be used to bind to negatively charged sulphate or carboxyl groups of acid mucopolysaccharides. Derivatives of boronic acid imitate the binding properties of lectins by reversibly binding the vicinal cis-diols, at physiological pH [13]. Cis-diols are common structural configurations present in biomolecules such as glycoproteins, carbohydrates and nucleosides.…”

Section: Introductionmentioning

confidence: 99%

Microscopical Examination of the Localisation Patterns of Two Novel Rhodamine Derivatives in Normal and Neoplastic Colonic Mucosa

et al. 2001

View full text Add to dashboard Cite

Tissue characterisation by fluorescence imaging, using exogenous fluorophores, is a promising method for cancer detection. Histochemical alterations in the composition of mucins, when neoplastic transformations occur, could be exploited to derive more selective fluoroprobes indicative of early malignant transformation. The aim of this work was to develop and examine tumour selective fluoroprobes for colon cancer diagnosis, as well as to determine the morphological components where selective dye accumulation has occurred. Two novel fluoroprobes: rhodamine B-L-leucine amide and rhodamine B-phenylboronic acid were synthesised and examined together with Mayer's mucicarmine, alexa 350-wheat germ agglutinin (WGA) and tetramethyl rhodamine-concanavalin A (ConA). Fluorescence microscopy studies were performed with deparaffinised human colon sections, using an epifluorescence microscope equipped with a colour CCD camera. The intense accumulation of the novel fluoroprobes was localised in the amorphous material in the lumen of neoplastic crypts. To gain insight into the localisation patterns, mucicarmine, alexa 350-WGA and tetramethyl rhodamine-ConA were used. Alexa 350-WGA reacted primarily with mucin secreted in the malignant crypt lumen suggesting that this material is rich in sialic acid and N-acetylglucosaminyl residues. These derivatives clearly and consistently distinguished non-neoplastic from neoplastic human colon tissue sections. The intense accumulation at the altered mucins indicates that they could be used as fluoroprobes of biochemical alterations for carcinoma detection.

show abstract

Synthesis of a fluorescent boronic acid which reversibly binds to cell walls and a diboronic acid which agglutinates erythrocytes

Cited by 59 publications

References 18 publications

Boron-Carbohydrate Interactions

Boron-Carbohydrate Interactions

Use of Phenylboronic Acids to Investigate Boron Function in Plants. Possible Role of Boron in Transvacuolar Cytoplasmic Strands and Cell-to-Wall Adhesion

Microscopical Examination of the Localisation Patterns of Two Novel Rhodamine Derivatives in Normal and Neoplastic Colonic Mucosa

Contact Info

Product

Resources

About