The Chirality of Aggregated Yariv Reagents Correlates with Their AGP‐Binding Ability**

Hoshing, Raghuraj; Leeber, Blaise W.; Kuhn, Helene; Caianiello, David; Dale, Brandon; Saladino, Michael; Lusi, Robert; Palaychuk, Natalie; Weingarten, Sarah; Basu, Amit

doi:10.1002/cbic.202100532

Cited by 3 publications

(8 citation statements)

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“…While MAbs can provide bright images showing AGP decoration, they are highly epitope specific, and due to their large size, the antibodies may not be able to access all parts of the cell wall. , On the other hand, the Yariv reagents, dyes based on a tri-glycosylated phloroglucinol core (Figure ), bind AGPs but can only be visualized using the less sensitive brightfield microscopy. The AGP binding ability of the Yariv reagents depends on the structure of the sugar moieties attached to the aromatic core. , Yariv reagents bearing β- d linked glucose (βGlcYariv) or galactose bind strongly to AGPs and have been used to isolate AGPs from plants by precipitation of an AGP–Yariv complex. − Yariv reagents comprised of α-linked sugars or l sugars do not bind to AGPs. The Yariv reagents aggregate in solution and bind to the core β(1 → 3)-linked galactan backbone, which is postulated to be helical. , We have used circular dichroism (CD) spectroscopy to show that the Yariv reagent aggregates are also helical, and that the sense and magnitude of helicity correlate with AGP binding ability .…”

Section: Introductionmentioning

confidence: 99%

“…20,21 We have used circular dichroism (CD) spectroscopy to show that the Yariv reagent aggregates are also helical, and that the sense and magnitude of helicity correlate with AGP binding ability. 16 The Yariv reagents are exceptionally selective for AGPs and do not bind strongly to other polysaccharides present in the plant cell wall. Given the specificity of Yariv reagents for AGPs, they are an excellent scaffold for designing a fluorescent probe for this important cell wall component.…”

Section: Introductionmentioning

confidence: 99%

“…The AGP binding ability of the Yariv reagents depends on the structure of the sugar moieties attached to the aromatic core. 15,16 Yariv reagents bearing β-D linked glucose (βGlcYariv) or galactose bind strongly to AGPs and have been used to isolate AGPs from plants by precipitation of an AGP−Yariv complex. 17 linked sugars or L sugars do not bind to AGPs.…”

Section: Introductionmentioning

confidence: 99%

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A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

et al. 2023

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Small molecule fluorescent probes that bind selectively to plant cell wall polysaccharides have been instrumental in elucidating the localization and function of these glycans. Arabinogalactan proteins (AGPs) are cell wall proteoglycans implicated in essential functions such as cell signaling, plant growth, and programmed cell death. There is currently no small molecule probe capable of fluorescently labeling AGPs. The Yariv reagents are the only small molecules that bind AGPs, and have been used to study AGP function and isolate AGPs via precipitation of an AGP− Yariv complex. However, the Yariv reagents are not fluorescent, rendering them ineffective for localization studies using fluorescence microscopy. A fluorescent version of a Yariv reagent that is capable of both binding as well as imaging AGPs would provide a powerful tool for studying AGPs in planta. Herein, we describe the synthesis of an azido analog of the Yariv reagent that can be further functionalized with a fluorophore to provide a glycoconjugate that binds AGPs and is fluorescent. We show that the modified reagent binds gum arabic in in vitro binding assays when used in conjunction with the βGlcYariv reagent. Fluorescent imaging of AGPs in fixed maize leaf tissue enables localization of AGPs to cell walls in the leaf. Significantly, imaging can also be carried out using fresh tissue. This represents the first small molecule probe that can be used to visualize AGPs using fluorescence microscopy.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

et al. 2023

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show abstract

“…The AGP binding ability of the Yariv reagents depends on the structure of the sugar moieties attached to the aromatic core. 15,16 Yariv reagents bearing β-D linked glucose (βGlcYariv) or galactose bind strongly to AGPs and have been used to isolate AGPs from plants by precipitation of an AGP-Yariv complex. 17- 19 Yariv reagents with α linked sugars or using L sugars do not bind to AGP.…”

Section: Introductionmentioning

confidence: 99%

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

Rueda

McCubbin

Shieh

et al. 2023

Preprint

View full text Add to dashboard Cite

Small molecule fluorescent probes that bind selectively to plant cell wall polysaccharides have been instrumental in elucidating the localization and function of these glycans. Arabinogalactan proteins (AGPs) are cell wall proteoglycans implicated in essential functions such as cell signaling, plant growth, and programmed cell death. There is currently no small molecule probe capable of fluorescently labeling AGPs. The Yariv reagents are the only small molecules that bind AGP, and have been used to study AGP function and isolate AGPs via precipitation of an AGP-Yariv complex. However, the Yariv reagents are not fluorescent, rendering them ineffective for localization studies using fluorescence microscopy. A fluorescent version of a Yariv reagent that is capable of both binding as well as imaging AGPs would provide a powerful tool for studying AGPs in planta. Herein, we describe the synthesis of an azido analog of the Yariv reagent that can be further functionalized with a fluorophore to provide a glycoconjugate that binds AGP and is fluorescent. We show that the modified reagent binds gum arabic in in vitro binding assays when used in conjunction with the βGlcYariv reagent. Fluorescent imaging of AGP in fixed maize leaf tissue enables localization of AGP to cell walls in the leaf. Significantly, imaging can also be carried out using fresh tissue. This represents the first small molecule probe that can be used to visualize AGP using fluorescence microscopy.

show abstract

“…20,21 We have used circular dichroism (CD) spectroscopy to show that the Yariv reagent aggregates are also helical, and that the sense and magnitude of helicity correlates with AGP binding ability. 16 The Yariv reagents are exceptionally selective for AGPs and do not strongly bind to other polysaccharides present in the plant cell wall. Given the specificity of Yariv reagents for AGP, they are an excellent scaffold for designing a fluorescent probe for this important cell wall component.…”

Section: Introductionmentioning

confidence: 99%

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

Rueda

McCubbin

Shieh

et al. 2023

Preprint

View full text Add to dashboard Cite

Small molecule fluorescent probes that bind selectively to plant cell wall polysaccharides have been instrumental in elucidating the localization and function of these glycans. Arabinogalactan proteins (AGPs) are cell wall proteoglycans implicated in essential functions such as cell signaling, plant growth, and programmed cell death. There is currently no small molecule probe capable of fluorescently labeling AGPs. The Yariv reagents are the only small molecules that bind AGP, and have been used to study AGP function and isolate AGPs via precipitation of an AGP-Yariv complex. However, the Yariv reagents are not fluorescent, rendering them ineffective for localization studies using fluorescence microscopy. A fluorescent version of a Yariv reagent that is capable of both binding as well as imaging AGPs would provide a powerful tool for studying AGPs in planta. Herein, we describe the synthesis of an azido analog of the Yariv reagent that can be further functionalized with a fluorophore to provide a glycoconjugate that binds AGP and is fluorescent. We show that the modified reagent binds gum arabic in in vitro binding assays when used in conjunction with the βGlcYariv reagent. Fluorescent imaging of AGP in fixed maize leaf tissue enables localization of AGP to cell walls in the leaf. Significantly, imaging can also be carried out using fresh tissue. This represents the first small molecule probe that can be used to visualize AGP using fluorescence microscopy.

show abstract

The Chirality of Aggregated Yariv Reagents Correlates with Their AGP‐Binding Ability**

Cited by 3 publications

References 36 publications

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

A Functionalizable Analog of the Yariv Reagent for AGP Imaging using Fluorescence Microscopy

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