Boronic acid building blocks: tools for self assembly

Nishiyabu, Ryuhei; Kubo, Yuji; James, Tony D.; Fossey, John S.

doi:10.1039/c0cc02921a

Cited by 477 publications

(269 citation statements)

References 216 publications

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“…The head group of PI(4,5)P 2 contains phosphate and hydroxyl functionalities (see Figure 1a) that can be exploited for this purpose. For example, it is well established that ureas can form complementary hydrogen bonding interactions with phosphates (15)(16)(17)(18), while boronic acids have been successfully used for the molecular recognition of diols via the reversible formation of B-O covalent bonds (19,20). Thus, we designed a chemical receptor (PHDM) that utilizes ureas and boronic acids as recognition motifs (see Figure 1b).…”

Section: Design and Development Of A Chemical Receptor For Pi(45)pmentioning

confidence: 99%

A Small Molecule Mimicking a Phosphatidylinositol (4,5)-Bisphosphate Binding Pleckstrin Homology Domain

et al. 2011

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Inositol phospholipids have emerged as important key players in a wide variety of cellular functions. Among the seven existing inositol phospholipids, phosphatidylinositol (4,5)-bisphosphate (PI(4,5)P 2 ) has attracted much attention in recent years due to its important role in numerous cellular signaling events and regulations, which in turn impact several human diseases. This particular lipid is recognized in the cell by specific lipid binding domains, such as the Pleckstrin-homology (PH) domain, which is also employed as a tool to monitor this important lipid. Here, we describe the synthesis and biological characterization of a small molecule that mimics the PH domain as judged by its ability to bind specifically to only PI(4,5)P 2 and effectively compete with the PH domain in vitro and in a cellular environment.The binding constant of this small molecule PH domain mimetic (PHDM) was determined to be 17.6 ± 10.1 µM, similar in potency to the PH domain. Using NIH 3T3 mouse fibroblast cells we demonstrated that this compound is cell permeable and able to modulate PI(4,5)P 2 -dependent effects in a cellular environment such as the endocytosis of the transferrin receptor, loss of mitochondria as well as stress fiber formation. This highly PI(4,5)P 2 -specific chemical mimetic of a PH domain, is not only a powerful research tool, but might also be a lead compound in future drug developments targeting PI(4,5)P 2 -dependent diseases such as Lowe syndrome.

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Section: Design and Development Of A Chemical Receptor For Pi(45)pmentioning

confidence: 99%

A Small Molecule Mimicking a Phosphatidylinositol (4,5)-Bisphosphate Binding Pleckstrin Homology Domain

et al. 2011

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“…However, several factors such as mixing speed, temperature, pH, and the presence of boric acid on PGB-0 structure need to be controlled to minimize the by-product. Boric acid easily reacts with the other boric acid to produce boroxine (Nishiyabu et al, 2011). Our result demonstrated that PGB-0 inhibited cells growth of HER2 overexpressed-cancer cells and performed no effect on normal cells.…”

Section: Pgb-0 Decrease Her2 Expressionmentioning

confidence: 63%

Synthesis and Cytotoxic Activity of 2,5-Bis(4-Boronic Acid)benzylidine Cyclopentanone on Her2 Overexpressed-Cancer Cells

Utomo¹,

Putri²,

Pudjono³

et al. 2017

Indonesian J. Pharm.

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Development of chemotherapeutic agent and boron carrying pharmaceutical based on HER2 specific targeted is important due to its role in enhancing cancer progression. The purpose of this study is to synthesize curcumin analogue, namely Pentagamaboron-0 (PGB-0) or 2,5-bis(4-boronic acid)benzylidine cyclopentanone, and to explore the cytotoxic activity on HER2 overexpressed-cancer cells. MCF-7/HER2 was used as a model of HER2 overexpressed-cancer cells and NIH3T3 as normal cells. PGB-0 bound to ATP binding site of HER2 and EGFR based on molecular docking study. PGB-0 was synthesized resulting in 33% yield and was confirmed by IR, 1 HNMR, 13 CNMR and Mass spectroscopy. Based on MTT assay PGB-0 decreased cells viability on MCF-7/HER2 cells with IC 50 value of 270µM but performed no effect on NIH3T3 cells. Cell cycle analysis revealed that PGB-0 increased sub-G1 accumulation. PGB-0 decreased HER2 expression in a dose-dependent manner. We conclude that the new compound PGB-0 inhibits cell growth through cell death induction and decreased HER2 expression. Thus, PGB-0 is potential to be developed as a chemotherapeutic agent and boron carrying pharmaceutical targeted on the HER2 receptor.

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“…The supramolecular polymer gel was sensitive to three different external stimuli and a rapid self-healing property based on boron-catechol interactions was demonstrated. Other research groups also developed artificial stimuli-responsive gels, including pHresponsive [29][30][31][32][33] and sugar-responsive [34] polymer gels via boric-catechol complexation for biomaterials applications. In this study, we present a pH-responsive self-healing hydrogel, inspired by adhesive mussel proteins, based on 3,4-dihydroxyphenethylamine(or dopamine)-conjugated polyaspartamide.…”

Section: Introductionmentioning

confidence: 99%

Mussel-mimetic self-healing polyaspartamide derivative gel via boron-catechol interactions

Wang¹,

Jeon²,

Park³

et al. 2015

Express Polym. Lett.

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Abstract. The catechol group from catechol of 3,4-dihydroxyphenethylamine (DOP, dopamine) has the ability to interact with metal ions to form non-covalent bonds in polymer chains. In this study, a novel kind of mussel-inspired copolymer, dopamine-conjugated poly(hydroxyethyl aspartamide), polyAspAm(DOP/EA), was synthesized and its interaction with boric acid (H 3 BO 3 ) to form a cross-linked gel via boron-catechol coordinative binding was investigated. The copolymer was designed to contain a pH responsive adhesive catechol group, which reversibly underwent gelation through the metalcatechol binding, as proved by UV-Vis spectroscopy. When the pH is increased from acidic conditions to a specified pH (pH > 9), the B(OH) 3 is considered to have a functionality of two to bind catechols, leading to bis-complexes. In addition, the reversibility of the boron-catechol bonds provides self-healing characteristics to the polyAspAm gels. The rheological results showed that boron-catechol coordination could lead to quick and full recovery after the fracture of a gel specimen. This novel pH-responsive and self-healing gel system has potential in various applications including smart hydrogels, medical adhesives, and sealants.

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Boronic acid building blocks: tools for self assembly

Cited by 477 publications

References 216 publications

A Small Molecule Mimicking a Phosphatidylinositol (4,5)-Bisphosphate Binding Pleckstrin Homology Domain

A Small Molecule Mimicking a Phosphatidylinositol (4,5)-Bisphosphate Binding Pleckstrin Homology Domain

Synthesis and Cytotoxic Activity of 2,5-Bis(4-Boronic Acid)benzylidine Cyclopentanone on Her2 Overexpressed-Cancer Cells

Mussel-mimetic self-healing polyaspartamide derivative gel via boron-catechol interactions

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