Binding Evaluation of Pradimicins for Oligomannose Motifs from Fungal Mannans

Nakagawa, Yu; Yamaji, Fumiya; Miyanishi, Wataru; Ojika, Makoto; Igarashi, Yasuhiro; Ito, Yukishige

doi:10.1246/bcsj.20200305

Cited by 8 publications

(7 citation statements)

References 48 publications

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“…These values are similar to those of PRM-Azide ( K d1 = 510 μM, K d2 = 8,100 μM), but higher than those of PRM-A ( K d1 = 96 μM, K d2 = 3800 μM), suggesting that the amide formation of PRM-A slightly decreases binding affinity for Man. However, considering the previous demonstration that PRM-Azide binds to fungal mannans, the binding affinity of PRM-EA for Man is sufficient for use in glycobiological research. Moreover, additional ITC experiments showed that PRM-EA was responsive to Man, but not to other monosaccharides ( d -glucose, d -galactose, N -acetyl- d -glucosamine, l -fucose, and N -acetylneuraminic acid methyl ester) found in biologically important glycans (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…This modification strategy was validated by the demonstration that PRM-Azide (Figure 1), an amide derivative of PRM-A, 1 retained Man binding ability. 27 This result represents a new direction in the design of PRM derivatives for glycobiological applications. Here, we report that amide formation at the C18 carboxyl group of PRMs can also address the issue related to aggregation.…”

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confidence: 83%

“…Subsequent molecular modeling suggested that amide formation at the C18 carboxyl group of PRMs would not disturb their complex formation with Ca 2+ and Man. This modification strategy was validated by the demonstration that PRM-Azide (Figure ), an amide derivative of PRM-A, retained Man binding ability . This result represents a new direction in the design of PRM derivatives for glycobiological applications.…”

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confidence: 90%

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A Pradimicin-Based Staining Dye for Glycoprotein Detection

et al. 2021

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Pradimicin A (PRM-A) and related compounds constitute an exceptional family of natural pigments that show Ca2+-dependent recognition of d-mannose (Man). Although these compounds hold great promise as research tools in glycobiology, their practical application has been severely limited by their inherent tendency to form water-insoluble aggregates. Here, we demonstrate that the 2-hydroxyethylamide derivative (PRM-EA) of PRM-A shows little aggregation in neutral aqueous media and retains binding specificity for Man. We also show that PRM-EA stains glycoproteins in dot blot assays, whereas PRM-A fails to do so, owing to severe aggregation. Significantly, PRM-EA is sensitive to glycoproteins carrying high mannose-type and hybrid-type N-linked glycans, but not to those carrying complex-type N-linked glycans. Such staining selectivity has never been observed in conventional dyes, suggesting that PRM-EA could serve as a unique staining agent for the selective detection of glycoproteins with terminal Man residues.

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Section: Resultsmentioning

confidence: 99%

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confidence: 83%

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confidence: 90%

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A Pradimicin-Based Staining Dye for Glycoprotein Detection

et al. 2021

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“…Synthetic approaches to nanoarchitect biomimetic molecules are often used in investigations of bioactive phenomena. Nakagawa et al synthesized various branched oligomannose derivatives that were subjected to evaluation of binding of pradimicins to oligosaccharides [ 101 ]. Pradimicins are known as a unique family of natural products with antifungal activity thorough binding with mannans at fungi cell walls.…”

Section: Synthetic Nanoarchitectonics For Bio-related Unitsmentioning

confidence: 99%

Biomimetic and Biological Nanoarchitectonics

Ariga

2022

IJMS

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A post-nanotechnology concept has been assigned to an emerging concept, nanoarchitectonics. Nanoarchitectonics aims to establish a discipline in which functional materials are fabricated from nano-scale components such as atoms, molecules, and nanomaterials using various techniques. Nanoarchitectonics opens ways to form a more unified paradigm by integrating nanotechnology with organic chemistry, supramolecular chemistry, material chemistry, microfabrication technology, and biotechnology. On the other hand, biological systems consist of rational organization of constituent molecules. Their structures have highly asymmetric and hierarchical features that allow for chained functional coordination, signal amplification, and vector-like energy and signal flow. The process of nanoarchitectonics is based on the premise of combining several different processes, which makes it easier to obtain a hierarchical structure. Therefore, nanoarchitectonics is a more suitable methodology for creating highly functional systems based on structural asymmetry and hierarchy like biosystems. The creation of functional materials by nanoarchitectonics is somewhat similar to the creation of functional systems in biological systems. It can be said that the goal of nanoarchitectonics is to create highly functional systems similar to those found in biological systems. This review article summarizes the synthesis of biomimetic and biological molecules and their functional structure formation from various viewpoints, from the molecular level to the cellular level. Several recent examples are arranged and categorized to illustrate such a trend with sections of (i) synthetic nanoarchitectonics for bio-related units, (ii) self-assembly nanoarchitectonics with bio-related units, (iii) nanoarchitectonics with nucleic acids, (iv) nanoarchitectonics with peptides, (v) nanoarchitectonics with proteins, and (vi) bio-related nanoarchitectonics in conjugation with materials.

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“…Thus, we evaluated the binding affinity of PRMs with thirteen oligomannoses (2-14; Fig. 9), 48) which reflected the structural motifs characteristic of the cell wall mannans from Candida albicans. 49) Oligomannoses (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were synthesized via a stepwise or blockwise glycosylation strategy using thiomannoside 50) and mannosyl halide donors.…”

Section: Binding Evaluation Of Prms For Oligomannosesmentioning

confidence: 99%

Mannose-binding analysis and biological application of pradimicins

Nakagawa

Ito

2022

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Pradimicins (PRMs) are an exceptional family of natural products that specifically bind D-mannose (Man). In the past decade, their scientific significance has increased greatly, with the emergence of biological roles of Man-containing glycans. However, research into the use of PRMs has been severely limited by their inherent tendency to form water-insoluble aggregates. Recently, we have established a derivatization strategy to suppress PRM aggregation, providing an opportunity for practical application of PRMs in glycobiological research. This article first outlines the challenges in studying Man-binding mechanisms and structural modifications of PRMs, and then describes our approach to address them. We also present our recent attempts toward the development of PRM-based research tools.

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Binding Evaluation of Pradimicins for Oligomannose Motifs from Fungal Mannans

Cited by 8 publications

References 48 publications

A Pradimicin-Based Staining Dye for Glycoprotein Detection

A Pradimicin-Based Staining Dye for Glycoprotein Detection

Biomimetic and Biological Nanoarchitectonics

Mannose-binding analysis and biological application of pradimicins

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