Category: 166821-88-1

Wang, Yan-en published the artcileSynthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen, Category: bromides-buliding-blocks, the publication is Chemical Research in Chinese Universities (2018), 34(3), 415-422, database is CAplus.

The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, authors reported the design and synthesis of a series of anthracene-based bisboronic acids (9a–9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.

Chemical Research in Chinese Universities published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C15H21BO2, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wiskur, Sheryl L. published the artcilepK_a Values and Geometries of Secondary and Tertiary Amines Complexed to Boronic Acids-Implications for Sensor Design, Synthetic Route of 166821-88-1, the publication is Organic Letters (2001), 3(9), 1311-1314, database is CAplus and MEDLINE.

The pK_a values and the geometries of secondary and tertiary amines adjacent to boronic acids (e.g. 2-(PhCH₂NRCH₂)C₆H₄B(OH)₂; R = H, Me) were determined using potentiometric and ¹¹B NMR titrations The studies showed that the secondary ammonium ion has a pK_a similar to that of the tertiary ammonium species, which gives tetrahedral B centers at pH values ≳5.5. Therefore, secondary amines as well as tertiary amines, when placed proximal to B centers, can be used to create tetrahedral boronic acids at neutral pH for diol complexation. The mol. structure of 2,6-(2-(2-((HO)₂B)C₆H₄CH₂NHCH₂)-4-pyrimidinyl)₂pyridine was determined by x-ray crystallog.

Organic Letters published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C8H8O3, Synthetic Route of 166821-88-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Wei published the artcileBuilding fluorescent sensors by template polymerization: the preparation of a fluorescent sensor for D-fructose, Application In Synthesis of 166821-88-1, the publication is Organic Letters (1999), 1(8), 1209-1212, database is CAplus and MEDLINE.

The application of mol. imprinting in making fluorescent sensors was hampered by the lack of suitable fluorescent tags, which would respond to the binding event with significant fluorescence intensity changes. The authors have designed and synthesized a fluorescent monomer which allows for the preparation of fluorescent sensors of cis diols using mol. imprinting methods. This monomer was used for the preparation of sensitive fluorescent sensors for D-fructose.

Organic Letters published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C7H8BFO2, Application In Synthesis of 166821-88-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Wenqian published the artcileThe First Fluorescent Diboronic Acid Sensor Specific for Hepatocellular Carcinoma Cells Expressing Sialyl Lewis X, Safety of 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, the publication is Chemistry & Biology (2004), 11(4), 439-448, database is CAplus and MEDLINE.

Carbohydrate antigens with subterminal fucosylation have been implicated in the development and progression of several cancers, including hepatocellular carcinoma (HCC). Fluorescent sensors targeting fucosylated carbohydrate antigens could potentially be used for diagnostic and other applications. The authors have designed and synthesized a series of 26 diboronic acid compounds as potential fluorescent sensors for such carbohydrates. Among these compounds, 7q was able to fluorescently label cells expressing high levels of sLex (HEPG2) within a concentration range of 0.5 to 10 μM. This compound (7q) did not label cells expressing Lewis Y (HEP3B), nor cells without fucosylated antigens (COS7). This represents the first example of a fluorescent compound labeling cells based on cell surface carbohydrate structures.

Chemistry & Biology published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C7H7ClN2, Safety of 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bielecki, Mia published the artcileA fluorescent glucose sensor binding covalently to all five hydroxy groups of α-D-glucofuranose. A reinvestigation, Synthetic Route of 166821-88-1, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1999), 449-456, database is CAplus.

The structures of the complexes between a fluorescent bisboronic acid 7 and glucose have been determined Shinkai et al.¹ previously studied the complex between 7 and glucose and they deduced a 1,2:4,6-α-D-glucopyranose bisboronate structure. We have shown that this structure is only valid as an initial complex formed under completely nonaqueous conditions. In the presence of water the pyranose complex rearranges rapidly into an α-D-glucofuranose-1,2:3,5,6-bisboronate in which all five free hydroxy groups of glucose are covalently bound by the sensor mol. A favorable B-N interaction around the 1,2-binding site and the effect of an o-ammoniomethyl group on the pK_a value of the second boronic acid group allow for the observed binding at neutral pH. The structure evaluations are based on ¹H and ¹³C NMR data as well as information obtained from ¹J_CC coupling constants The fluorescence spectra of both complexes were measured and discussed. MALDI TOF-MS experiments showed competitive formation of 1:2 (boronic acid:glucose) complexes under conditions of physiol. glucose levels.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C12H16BBrO2, Synthetic Route of 166821-88-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Uddin, Jamal Md. published the artcilePhotoinduced electron transfer quenching and sugar effects on the electrostatic interaction between an anionic Ru(II) complex and cationic bipyridinium derivatives functionalized with boronic acids, SDS of cas: 166821-88-1, the publication is Inorganica Chimica Acta (2012), 104-110, database is CAplus and MEDLINE.

The photoinduced electron transfer quenching of an anionic ruthenium(II) metal-ligand-complex (Ru(dpp(SO₃Na)))₂(mcbpy)Cl₂ by two boronic acid functionalized benzyl viologen (BV²⁺) derivatives has been investigated as well as their response to sugar. The electrostatic interaction between these two charge species lead to the formation of static quenching which is removed in presence of sugar due to the formation of a neutral zwitterionic quencher. Spectral data, quenching parameters and sugar titration curves are presented and discussed in term of future developments of optical sensors for sugar.

Inorganica Chimica Acta published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C11H8O3, SDS of cas: 166821-88-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Regueiro-Figueroa, Martin published the artcileMolecular Recognition of Sialic Acid by Lanthanide(III) Complexes through Cooperative Two-Site Binding, SDS of cas: 166821-88-1, the publication is Inorganic Chemistry (2010), 49(9), 4212-4223, database is CAplus and MEDLINE.

Herein the authors report two new ligands, 1,4,7-tris(carboxymethyl)-10-[2-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L¹) and 1,4,7-tris(carboxymethyl)-10-[3-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L²), which contain a phenylboronic acid (PBA) function and a 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate cage for complexation of lanthanide ions in an aqueous solution The pK_a of the PBA function amounts to 4.6 in [Gd(L¹)] and 8.9 in [Gd(L²)], with the value of the L² analog being very similar to that of PBA (8.8). These results are explained by the coordination of the PBA function of L¹ to the Gd^III ion, which results in a dramatic lowering of its pK_a. As a consequence, [Gd(L¹)] does not bind to saccharides at physiol. pH. The nuclear magnetic relaxation dispersion profiles recorded for [Gd(L¹)] and [Gd(L²)] confirm that the phenylboronate function is coordinated to the metal ion in the L¹ derivative, which results in a q = 0 complex. The interaction of the [Gd(L²)] complex with 5-acetylneuraminic acid (Neu5Ac) and 2-α-O-methyl-5-acetylneuraminic acid (MeNeu5Ac) was studied by spectrophotometric titrations in an aqueous solution (pH 7.4, 0.1M 3-(N-morpholino)propanesulfonic acid buffer). Also, the authors have also studied the binding of these receptors with competing monosaccharides such as D-(+)-glucose, D-fructose, D-mannose, D-galactose, Me α-D-galactoside, and Me α-D-mannoside. The binding constants obtained indicate an important selectivity of [Gd(L²)] for Neu5Ac (K_eq = 151) over D-(+)-glucose (K_eq = 12.3), D-mannose (K_eq = 21.9), and D-galactose (K_eq = 24.5). Also, a very weak binding affinity was observed in the case of Me α-D-galactoside and Me α-D-mannoside. An 8-fold increase of the binding constant of [Gd(L²)] with Neu5Ac is observed when compared to that of PBA determined under the same conditions (K_eq = 19). ¹³C NMR spectroscopy and d. functional theory calculations performed at the B3LYP/6-31G(d) level show that this is due to a cooperative two-site binding of Neu5Ac through (1) ester formation by interaction on the PBA function of the receptor and (2) coordination of the carboxylate group of Neu5Ac to the Gd^III ion. The emission lifetime of the ⁵D₄ level of Tb^III in [Tb(L²)] increases upon Neu5Ac binding, in line with the displacement of inner-sphere water mols. due to coordination of Neu5Ac to the metal ion.

Inorganic Chemistry published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C12H16BBrO2, SDS of cas: 166821-88-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary