Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Glycans in the form of glycoproteins or glycolipids play very critical roles in various biological and pathological processes including inflammation, cancer metastasis, immune reactions, embryo development, cell–cell communications and adhesions, blood generation, etc. Proteins (lectins) that can recognize carbohydrates have played very important roles in studying glycobiology. Small molecule mimics of lectins will be very useful in the development of new therapeutics and diagnostics. Along this line, boronic acids have been widely used in the design and synthesis of small organic compounds that mimic the function of lectins. This review examines in detail the factors that are important for the design of boronic acid‐based lectin mimics, boronolectins. © 2005 Wiley Periodicals, Inc.

[1]  G. Springsteen,et al.  Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates. , 2001, Chemical communications.

[2]  H. Kuivila,et al.  ARENEBORONATES FROM DIOLS AND POLYOLS1 , 1954 .

[3]  T. James,et al.  The B-N bond controls the balance between locally excited (LE) and twisted internal charge transfer (TICT) states observed for aniline based fluorescent saccharide sensors , 2004 .

[4]  R. Oriol,et al.  A Missense Mutation in the FUT6 Gene Results in Total Absence of α3-Fucosylation of Human α1-Acid Glycoprotein* , 1996, The Journal of Biological Chemistry.

[5]  S. Shinkai,et al.  Saccharide Sensing with Molecular Receptors Based on Boronic Acid , 1996 .

[6]  A. Lundblad,et al.  E‐Selectin: Sialyl Lewis, a Dependent Adhesion of Colon Cancer Cells, is Inhibited Differently by Antibodies Against E‐Selectin Ligands , 1996, Scandinavian journal of immunology.

[7]  S. Shinkai,et al.  Recognition of sugars and related compounds by “reading-out”-type interfaces , 1995 .

[8]  A. Varki,et al.  Differential colon cancer cell adhesion to E-, P-, and L-selectin: role of mucin-type glycoproteins. , 1995, Cancer research.

[9]  Joop A. Peters,et al.  pH dependence of the stability of boric acid and borate esters of amino acids and amino diols in aqueous medium as studied by 1B and 1H NMR spectroscopy , 1989 .

[10]  T. Yoshii,et al.  CD29 and CD7 mediate galectin-3-induced type II T-cell apoptosis. , 2003, Cancer research.

[11]  M. Badawi,et al.  Boronic acids for affinity chromatography: spectral methods for determinations of ionization and diol-binding constants. , 1989, Analytical biochemistry.

[12]  M. Bulmer.  The maintenance of the genetic variability of polygenic characters by heterozygous advantage. , 1973, Genetical research.

[13]  S. Spiegel,et al.  Glycosphingolipids and cell death , 2003, Glycoconjugate Journal.

[14]  A. Cerami,et al.  Glycosylated Insulin Complexed to Concanavalin A: Biochemical Basis for a Closed-Loop Insulin Delivery System , 1983, Diabetes.

[15]  P. Wood,et al.  Synthesis, and p.m.r. and mass spectra of some boronic esters of carbohydrates , 1974 .

[16]  W. Scouten,et al.  New ligands for boronate affinity chromatography , 1994 .

[17]  B. Hargitay,et al.  192. The structure and relative stabilities of boric esters of 1,2- and 1,3-diols , 1961 .

[18]  B. Wang,et al.  New boronic acid fluorescent reporter compounds. 2. A naphthalene-based on-off sensor functional at physiological pH. , 2003, Organic letters.

[19]  S. Shinkai,et al.  Two dimensional photoinduced electron transfer(PET) fluorescence sensor for saccharides , 1995 .

[20]  S. Shinkai,et al.  Exploitation of a novel 'on-off' photoinduced electron-transfer (PET) sensor against conventional 'off-on' PET sensors , 1999 .

[21]  Tony D. James,et al.  Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine , 1995 .

[22]  Masafumi Mikami,et al.  Molecular fluorescence sensor for saccharides based on amino coumarin , 1995 .

[23]  J. Edwards,et al.  THE THERMODYNAMICS OF IONIZATION OF BENZENEBORONIC ACID , 1961 .

[24]  J. C. Norrild,et al.  Boronic acids as fructose sensors. Structure determination of the complexes involved using 1JCC coupling constants , 1996 .

[25]  B. Wang,et al.  Naphthalene-based water-soluble fluorescent boronic acid isomers suitable for ratiometric and off-on sensing of saccharides at physiological pH , 2005 .

[26]  S. Shinkai,et al.  Spectroscopic detection of diols and sugars by a colour change in boronic acid-appended spirobenzopyrans , 1996 .

[27]  S. Shinkai,et al.  Selective binding of glucose-6-phosphate, 3,4-dihydroxyphenylalanine (DOPA) and their analogs with a boronic-acid-appended metalloporphyrin , 1996 .

[28]  S. Shinkai,et al.  Sugar-induced chiral orientation of a boronic-acid-appended porphyrin stack. Correlation between the absolute configuration and the CD (circular dichroism) sign , 1994 .

[29]  J. C. Norrild.  An illusive chiral aminoalkylferroceneboronic acid. Structural assignment of a strong 1 ∶ 1 sorbitol complex and new insight into boronate–polyol interactions , 2001 .

[30]  Isabelle Camby,et al.  Galectins and cancer. , 2002, Biochimica et biophysica acta.

[31]  S. Shinkai,et al.  Determination of the absolute configuration of monosaccharides by a colour change in a chiral cholesteric liquid crystal system , 1993 .

[32]  S. Shinkai,et al.  Novel fluorescence sensor for ‘small’saccharides , 1997 .

[33]  J. Lakowicz.  Principles of fluorescence spectroscopy , 1983 .

[34]  E. Anslyn,et al.  A competition assay for determining glucose-6-phosphate concentration with a tris-boronic acid receptor , 1999 .

[35]  He,et al.  Visual sensing of saccharides promoted by resorcinol condensation products , 2000, Organic letters.

[36]  C. Bowman,et al.  Cyclic Benzeneboronate Esters , 1958 .

[37]  Joop A. Peters,et al.  Structure and stability, as a function of pH, of borate esters of carbohydrate oximes and related compounds in aqueous media studied by 11B and 13C NMR spectroscopy , 1991 .

[38]  A. Davis,et al.  Hydrogen Bonding, Hydrophobic Interactions, and Failure of the Rigid Receptor Hypothesis. , 1999, Angewandte Chemie.

[39]  G. Springsteen,et al.  The design of boronic acid spectroscopic reporter compounds by taking advantage of the pK(a)-lowering effect of diol binding: nitrophenol-based color reporters for diols. , 2004, The Journal of organic chemistry.

[40]  S. Shinkai,et al.  Sugar ‘Chirality’ Sensing Using a ‘Prochiral’ Salen–Co(II) Complex , 2000 .

[41]  S. Shinkai,et al.  Specific complexation with mono- and disaccharides that can be detected by circular dichroism , 1991 .

[42]  Tony D. James,et al.  Synthesis and evaluation of D-glucosamine-selective fluorescent sensors , 2000 .

[43]  J. Frederiksen,et al.  A New Glucose-Selective Fluorescent Bisboronic Acid. First Report of Strong α-Furanose Complexation in Aqueous Solution at Physiological pH1 , 1999 .

[44]  B. Wang,et al.  A NEW TYPE OF WATER-SOLUBLE FLUORESCENT BORONIC ACID SUITABLE FOR CONSTRUCTION OF POLYBORONIC ACIDS FOR CARBOHYDRATE RECOGNITION , 2004 .

[45]  J. Lakowicz,et al.  Spectral Properties of Fluorophores Combining the Boronic Acid Group with Electron Donor or Withdrawing Groups. Implication in the Development of Fluorescence Probes for Saccharides. , 2001, The journal of physical chemistry. A.

[46]  Tony D. James,et al.  Novel photoinduced electron-transfer sensor for saccharides based on the interaction of boronic acid and amine , 1994 .

[47]  Binghe Wang,et al.  The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears , 2004 .

[48]  S. Franzen,et al.  Regulating the fluorescence intensity of an anthracene boronic acid system: a B-N bond or a hydrolysis mechanism? , 2004, Bioorganic chemistry.

[49]  E. Anslyn,et al.  A colorimetric sensing ensemble for heparin. , 2002, Journal of the American Chemical Society.

[50]  Chi-Huey Wong,et al.  Carbohydrate Mimetics: A New Strategy for Tackling the Problem of Carbohydrate‐Mediated Biological Recognition , 1999 .

[51]  Binghe Wang,et al.  A detailed examination of boronic acid–diol complexation , 2002 .

[52]  Wei Wang,et al.  Boronic Acid-Based Sensors , 2002 .

[53]  Anthony W. Czarnik,et al.  Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching , 1992 .

[54]  H. van Bekkum,et al.  The structure and (local) stability constants of borate esters of mono- and di-saccharides as studied by 11B and 13C NMR spectroscopy. , 1992, Carbohydrate research.

[55]  P. Ashton,et al.  A molecular colour sensor for monosaccharides , 2000 .

[56]  T. Oi,et al.  Esterification of Boric Acid with 1,2-Propanediol, 3-Amino-1,2-propanediol, and (±)-3-Dimethylamino-1,2-propanediol as Studied by 11B NMR Spectroscopy , 1992 .

[57]  John O. Edwards,et al.  Polyol Complexes and Structure of the Benzeneboronate Ion , 1959 .

[58]  V. Lynch,et al.  pK(a) values and geometries of secondary and tertiary amines complexed to boronic acids-implications for sensor design. , 2001, Organic letters.

[59]  B. Wang,et al.  Diboronic acids as fluorescent probes for cells expressing sialyl Lewis X. , 2002, Bioorganic & medicinal chemistry letters.

[60]  Anthony W. Czarnik,et al.  Chemical Communication in Water Using Fluorescent Chemosensors , 1994 .

[61]  T. James,et al.  Boronic acid appended azo dyes–colour sensors for saccharidesElectronic supplementary information (ESI) available: absorption–pH titrations and absorption–saccharide titrations. See http://www.rsc.org/suppdata/p1/b1/b108896c/ , 2002 .

[62]  J. Böeseken,et al.  The use of Boric Acid for the Determination of the Configuration of Carbohydrates , 1949 .

[63]  S. Shinkai,et al.  A novel light-gated sugar receptor, which shows high glucose selectivity , 1998 .

[64]  S. Shinkai,et al.  Molecular Design of Boronic Acid-Based Dye Receptors for Nucleosides , 1996 .

[65]  L. Szebellédy,et al.  Beiträge zum Nachweis der Borsäure mit Alizarin , 1936 .

[66]  R. Pizer,et al.  Equilibria and reaction mechanism of the complexation of methylboronic acid with polyols , 1992 .

[67]  M. Heagy,et al.  Fluorescent chemosensor for carbohydrates which shows large change in chelation-enhanced quenching , 1999 .

[68]  H. Suenaga,et al.  Screening of fluorescent boronic acids for sugar sensing which show a large fluorescence change , 1995 .

[69]  Jun Yan,et al.  A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH. , 2003, Bioorganic & medicinal chemistry letters.

[70]  J. Lakowicz,et al.  A new highly fluorescent probe for monosaccharides based on a donor-acceptor diphenyloxazole. , 2001, Chemical communications.

[71]  Zhiqing Yan,et al.  Density functional study of the lithiation of cyclic vinyl ethers in solution , 2004 .

[72]  L. Babcock,et al.  Mechanism of the complexation of boron acids with catechol and substituted catechols , 1977 .

[73]  Joop A. Peters,et al.  Studies on borate esters II , 1984 .

[74]  T. Feizi.  Demonstration by monoclonal antibodies that carbohydrate structures of glycoproteins and glycolipids are onco-developmental antigens , 1985, Nature.

[75]  Dale G. Drueckhammer,et al.  Computer-Guided Design in Molecular Recognition: Design and Synthesis of a Glucopyranose Receptor This work was supported by the National Institutes of Health (grant DK5523402). , 2001, Angewandte Chemie.

[76]  T. Mukherjee,et al.  Photodynamics of the S1 state of some hydroxy- and amino-substituted naphthoquinones and anthraquinones , 1990 .

[77]  J. Verchere,et al.  Formation of neutral complexes of boric acid with 1,3-diols in organic solvents and in aqueous solution , 1995 .

[78]  Jun Yan,et al.  The first fluorescent sensor for D-glucarate based on the cooperative action of boronic acid and guanidinium groups. , 2003, Chemical communications.

[79]  S. Shinkai,et al.  A Glucose-Selective Molecular Fluorescence Sensor† , 1994 .

[80]  Stefano Iacobelli,et al.  90K (Mac-2 BP) and galectins in tumor progression and metastasis , 2004, Glycoconjugate Journal.

[81]  J. L. Goodman,et al.  Leukocyte infection by the granulocytic ehrlichiosis agent is linked to expression of a selectin ligand. , 1999, The Journal of clinical investigation.

[82]  A. Dell,et al.  A role for glycoconjugates in human development: the human feto-embryonic defence system hypothesis. , 1996, Human reproduction.

[83]  K. Kissel,et al.  Molecular basis of the neutrophil glycoprotein NB1 (CD177) involved in the pathogenesis of immune neutropenias and transfusion reactions , 2001, European journal of immunology.

[84]  T. Gibson,et al.  Detection of total sugar concentration using photoinduced electron transfer materials: development of operationally stable, reusable optical sensors , 2000 .

[85]  S. Shinkai,et al.  Specific complexation of disaccharides with diphenyl-3,3′-diboronic acid that can be detected by circular dichroism , 1992 .

[86]  S. Shinkai,et al.  Spectroscopic sugar sensing by a stilbene derivative with push (Me2N-)-pull ((HO)2B-)-type substituents , 1995 .

[87]  J. Lakowicz,et al.  Chalcone-analogue fluorescent prfobes for saccharides signaling using the boronic acid group. , 2002, Tetrahedron letters.

[88]  D. C. Roberts,et al.  Chemical affinity systems—I: pH dependence of boronic acid-diol affinity in aqueous solution , 1980 .

[89]  Joop A. Peters,et al.  Studies on borate esters II: Structure and stability of borate esters of polyhydroxycarboxylates and related polyols in aqueous alkaline media as studied by 11B NMR , 1985 .

[90]  G. Wulff,et al.  Selective binding to polymers via covalent bonds. The construction of chiral cavities as specific receptor sites , 1982 .

[91]  B. Wang,et al.  The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X. , 2004, Chemistry & biology.

[92]  M. Heagy,et al.  Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides. , 2004, The Journal of organic chemistry.

[93]  J. C. Norrild,et al.  Evidence for Mono- and Bisdentate Boronate Complexes of Glucose in the Furanose Form. Application of 1JC-C Coupling Constants as a Structural Probe , 1995 .

[94]  J. Sodroski,et al.  Factors limiting the immunogenicity of HIV-1 gp120 envelope glycoproteins. , 2004, Virology.

[95]  S. Shinkai,et al.  Oligosaccharide binding to a boronic-acid-appended phenanthroline·Cu(I) complex which creates superstructural helicates and catenates , 2002 .

[96]  R. Singhal,et al.  New ligands for boronte affinity chromatography , 1991 .

[97]  E. J. Bourne,et al.  695. Phenylboronates of acyclic polyhydroxy-compounds , 1965 .

[98]  T. James,et al.  Binary and ternary phenylboronic acid complexes with saccharides and Lewis bases , 2004 .

[99]  J. Lakowicz,et al.  Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose. , 2002, Organic letters.

[100]  Dale G. Drueckhammer,et al.  Computer‐Guided Design in Molecular Recognition: Design and Synthesis of a Glucopyranose Receptor , 2001 .

[101]  A. Krześlak,et al.  Differences in glycosylation of intracellular proteins between benign and malignant thyroid neoplasms. , 2003, Cancer letters.

[102]  Charge transfer fluorescent probes using boronic acids for monosaccharide signaling. , 2002, Journal of biomedical optics.

[103]  R. Juliano,et al.  Antisense inhibition of P-glycoprotein expression using peptide-oligonucleotide conjugates. , 2000, Biochemical pharmacology.

[104]  J. Lakowicz,et al.  Wavelength-ratiometric probes for saccharides based on donor-acceptor diphenylpolyenes. , 2001, Journal of photochemistry and photobiology. A, Chemistry.

[105]  S. Franzen,et al.  Study of the Mechanism of Electron-Transfer Quenching by Boron−Nitrogen Adducts in Fluorescent Sensors , 2003 .

[106]  T. James,et al.  Fluorescent internal charge transfer (ICT) saccharide sensor , 2001 .

[107]  J. Moniz-Pereira,et al.  Identification and characterization of HIV-2 strains obtained from asymptomatic patients that do not use CCR5 or CXCR4 coreceptors. , 2003, Virology.

[108]  Tony D James,et al.  Molecular color sensors for monosaccharides. , 2002, Organic letters.

[109]  M. Hanski,et al.  Altered glycosylation of the MUC-1 protein core contributes to the colon carcinoma-associated increase of mucin-bound sialyl-Lewis(x) expression. , 1993, Cancer research.

[110]  E. J. Bourne,et al.  A convenient method for the synthesis of 6-O-methyl-D-glucose , 1972 .

[111]  B. Wang,et al.  A glucose-selective fluorescence sensor based on boronic acid-diol recognition. , 2002, Bioorganic & medicinal chemistry letters.

[112]  I. Hamachi,et al.  A Novel Sugar Sensing System Designed with a Cooperative Action of a Boronic-Acid-Appended Zinc Porphyrin and a 3-Pyridylboronic Acid Axial Ligand , 1997 .

[113]  F. Tani,et al.  Chirality control of a Cu(I)·(phenanthroline)2 complex by a sugar–boronic acid interaction. A preliminary step toward the total chain helicity control by a chain-end sugar-binding , 2000 .