Synthesis of ganglioside analogs containing fluorescently labeled GalNAc for single-molecule imaging

Koikeda, Machi; Komura, Naoko; Tanaka, Hidenori; Imamura, Akira; Ishida, Hideyuki; Kiso, Makoto; Ando, Hiromune

doi:10.1080/07328303.2019.1609019

Cited by 7 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The gangliosides GM1 (bovine brain), GD1a (bovine brain) and GD2 (human brain) were purchased from Avanti Polar Lipids, AdipoGen Life Sciences and Santa Cruz, respectively. GM2, GM3, and GD3 were prepared by total chemical synthesis (Koikeda et al, 2019; Takahashi et al, 2020). In an eggplant-shaped flask, 50 μl of 1 mM ganglioside (GM1, GM2, GM3, GD1a, GD2, or GD3) in methanol, 500 μl of 10 mM DMPC in chloroform, and 0.5 μl of 1 mM Bodipy-SM (Invitrogen) in methanol were mixed in a solution of 99:1:0.01 mol% ratio DMPC:ganglioside:Bodipy-SM.…”

Section: Methodsmentioning

confidence: 99%

Extracellular vesicles adhere to cells predominantly through the interaction of CD151-associated integrin heterodimers and GM1 with laminin

Isogai,

Hirosawa,

Kanno

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

Tumor-derived extracellular vesicles (EVs) have attracted significant attention, yet the molecular mechanisms that govern their specific binding to recipient cells remain elusive. Our in vitro study utilizing single-particle tracking demonstrated that integrin heterodimers comprising α6β4 and α6β1 are responsible for the binding of small-EV (sEV) subtypes to laminin. EVs derived from four distinct tumor cell lines, regardless of size, exhibited high binding affinities for laminin but not for fibronectin, although fibronectin receptors are abundant in EVs and have functional roles in EV-secreting cells. Our findings also revealed that the robust binding of integrins in EVs to laminin is preserved by CD151 rather than by talin-1 inside-out signaling and is inhibited by a molecule that associates with CD151 via cholesterol. The sEV-laminin interaction is also induced by GM1. Super-resolution movie observation revealed that sEV integrins bind only to laminin on living recipient cells. Thus, we demonstrated that all EV subtypes bind to laminin predominantly via CD151-facilitated integrin heterodimers and GM1.

show abstract

Section: Methodsmentioning

confidence: 99%

Extracellular vesicles adhere to cells predominantly through the interaction of CD151-associated integrin heterodimers and GM1 with laminin

Isogai,

Hirosawa,

Kanno

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…We also synthesized GalNAc‐GD1a labeled with the ATTO594 dye at position C6 of the terminal galactosamine (594‐G6‐GalNAc‐GD1a 160 , Scheme 38). [99] The desired glycan assembly was constructed using a convergent glycosylation strategy. Trisaccharide donor 157 was obtained by coupling acceptor 155 with 6‐azido GalNAc donor 156 .…”

Section: Synthesis Of Gangliosidesmentioning

confidence: 99%

Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses

Vibhute

Komura

Tanaka

et al. 2021

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Sialic acid is an important component of cell surface glycans, which are responsible for many vital body functions and should therefore be thoroughly studied to understand their biological roles and association with disorders. The difficulty of isolating large quantities of homogenous‐state sialoglycans from natural sources has inspired the development of the corresponding chemical synthesis methods affording acceptable purities, yields, and amounts. However, the related syntheses are challenging because of the difficulties in α‐glycosylation of sialic acid, which arises from its certain structural features such as the absence of a stereodirecting group at the C3 position and presence of carboxyl group at the anomeric position. Moreover, the structural complexities of sialoglycans with diverse numbers and locations of sialic acid on the glycan chains pose additional barriers. Thus, efficient α‐stereoselective routes to sialosides remain highly sought after, although various types of sialyl donors/acceptors have been developed for the straightforward synthesis of α‐sialosides. Herein, we review the latest progress in the α‐stereoselective synthesis of sialosides and their applications in the preparation of gangliosides and other sialoglycans.

show abstract

“…This technique enables observation of ganglioside dynamics in living cell PMs at the individual molecule level. 4 In previous research, fluorescent ganglio- 5–7 and globo-series 8,9 ganglioside probes were chemically synthesized, which exhibited properties similar to those of natural gangliosides. We used single-molecule imaging in living cells to investigate the behavior of these probes, as well as their cis interactions with raft-associated membrane proteins, such as GPI-anchored proteins.…”

Section: Introductionmentioning

confidence: 99%

Development of lacto-series ganglioside fluorescent probe using late-stage sialylation and behavior analysis with single-molecule imaging

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

Synthesis of ganglioside analogs containing fluorescently labeled GalNAc for single-molecule imaging

Cited by 7 publications

References 20 publications

Extracellular vesicles adhere to cells predominantly through the interaction of CD151-associated integrin heterodimers and GM1 with laminin

Extracellular vesicles adhere to cells predominantly through the interaction of CD151-associated integrin heterodimers and GM1 with laminin

Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses

Development of lacto-series ganglioside fluorescent probe using late-stage sialylation and behavior analysis with single-molecule imaging

Contact Info

Product

Resources

About