Notes- A Convenient Synthesis of Water-Soluble Carbodiimides.

Sheehan, John C.; Cruickshank, Philip A.; Boshart, Gregory

doi:10.1021/jo01351a600

Cited by 419 publications

(192 citation statements)

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“…26À28 Carboxylmethyl-dimannose was obtained by ozonolysis of the alkene, 29 followed by further oxidation with Jones reagent. 26 Global deprotection under Birch reduction 30 furnished the fully deprotected α-1,2-linked dimannose ( Figure 1B).…”

Section: Abstract: Polyanhydrides Nanoparticles Carbohydrates Dendmentioning

confidence: 99%

“…Lactose and dimannose were conjugated on the surface of polyanhydride nanoparticles by an amineÀcarboxylic acid coupling reaction. 28,30,31 Lactose, a neutral sugar with the same molecular weight as dimannose, was chosen as a control sugar because of its different stereochemical configuration compared to dimannoside. Particles with glycolic Molecular Pharmaceutics ARTICLE acid groups on the surface (linker groups) and nonfunctionalized (NF) particles were used as controls.…”

Section: Abstract: Polyanhydrides Nanoparticles Carbohydrates Dendmentioning

confidence: 99%

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Mannose-Functionalized “Pathogen-like” Polyanhydride Nanoparticles Target C-Type Lectin Receptors on Dendritic Cells

et al. 2011

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Targeting pathogen recognition receptors on dendritic cells (DCs) offers the advantage of triggering specific signaling pathways to induce a tailored and robust immune response. In this work, we describe a novel approach to targeted antigen delivery by decorating the surface of polyanhydride nanoparticles with specific carbohydrates to provide "pathogen-like" properties that ensure nanoparticles engage C-type lectin receptors on DCs. The surface of polyanhydride nanoparticles was functionalized by covalent linkage of dimannose and lactose residues using an amine-carboxylic acid coupling reaction. Coculture of functionalized nanoparticles with bone marrow-derived DCs significantly increased cell surface expression of MHC II, the T cell costimulatory molecules CD86 and CD40, the C-type lectin receptor CIRE and the mannose receptor CD206 over the nonfunctionalized nanoparticles. Both nonfunctionalized and functionalized nanoparticles were efficiently internalized by DCs, indicating that internalization of functionalized nanoparticles was necessary but not sufficient to activate DCs. Blocking the mannose and CIRE receptors prior to the addition of functionalized nanoparticles to the culture inhibited the increased surface expression of MHC II, CD40 and CD86. Together, these data indicate that engagement of CIRE and the mannose receptor is a key mechanism by which functionalized nanoparticles activate DCs. These studies provide valuable insights into the rational design of targeted nanovaccine platforms to induce robust immune responses and improve vaccine efficacy. The use of vaccine adjuvants to activate the innate immune system is crucial to vaccine effectiveness. 1 Adjuvants can be used to enhance the efficacy of single dose vaccines and reduce the required antigen dose. The use of biodegradable polymer nanoparticles as vaccine delivery vehicles allows for effective delivery of payloads by parental or mucosal administration by protecting the antigen from harsh physiological conditions and enabling transport across biological barriers (e.g., mucus membranes). 2 Polyanhydride nanoparticles have shown excellent potential as vaccine carriers. 3À6 Encapsulation of protein antigens into polyanhydride particles stabilizes them and provides sustained azntigen release; 4,7 these particles also enhance the immune response by acting as an adjuvant. 3 Dendritic cells (DCs) are antigen presenting cells (APCs) that play a major role in connecting the innate and adaptive immune systems, a key step to inducing protective immunity. 8 DCs can sense and internalize antigen by a variety of mechanisms that trigger DC maturation and direct further interactions with other immune cells, including naive T cells. 1,9,10 Pattern recognition receptors (PRRs) on DCs detect the presence of a potential threat by interacting with pathogen-associated molecular patterns (PAMPs). 10,11 In particular, C-type lectin receptors (CLRs) are PRRs with highly conserved carbohydrate-recognition domains that bind sugar moieties (e.g., mannose, fuco...

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Section: Abstract: Polyanhydrides Nanoparticles Carbohydrates Dendmentioning

confidence: 99%

Section: Abstract: Polyanhydrides Nanoparticles Carbohydrates Dendmentioning

confidence: 99%

Mannose-Functionalized “Pathogen-like” Polyanhydride Nanoparticles Target C-Type Lectin Receptors on Dendritic Cells

et al. 2011

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“…The modified linseed oil 3 was then grafted with DR1 (4) by esterification [38] to yield DR1-conjugated linseed oil (5) (Scheme 1 Reaction 2). 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) was used as a condensation reagent and 4-(Ddimethylamino)pyridine (DMAP) was used as a catalyst.…”

Section: Reaction 2: Synthesis Of Dr1-conjugated Linseed Oil (5)mentioning

confidence: 99%

Dye conjugation to linseed oil by highly-effective thiol-ene coupling and subsequent esterification reactions

2015

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Linseed oil, a renewable material obtained from the ripened seeds of the flax plant, was conjugated with C. I. Disperse Red 1 to yield a coloured macromolecule in two experimentally-simplistic coupling steps. Firstly, the abundant presence of carbon-carbon double bonds in linseed oil was exploited to introduce carboxylic acid functionality to linseed oil via a thiol-ene reaction between linseed oil and 3-mercaptopropionic acid. C. I. Disperse Red 1 was then grafted to the carboxylic acid units now present via esterification, offering a coloured product in high yields. On average, 39.1% of the carbon-carbon double bonds in each linseed oil molecule were furnished with a C. I. Disperse Red 1 molecule. The remaining carbon-carbon double bonds may therefore be further exploited for chemical crosslinking, ensuring that the product formed is of potential significance as a coloured, bio-based, surface coating product.

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“…In this project, the ketimine derivatives of amino acids (33) have been used to synthesize the hexapeptide sequences 6-11 in a stepwise manner from the carboxyl terminal methionine. The methods employed are outlined in Scheme 5.…”

Section: > 1 2 Imentioning

confidence: 99%