Mannosylated self-assembled structures for molecular confinement and gene delivery applications

Gour, Nidhi; Purohit, Chandra Shekhar; Verma, Sandeep; Puri, Rajat; Ganesh, Subramaniam

doi:10.1016/j.bbrc.2008.11.070

Cited by 14 publications

(6 citation statements)

References 30 publications

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“…Such a change in self‐assembly of diphenylalanine bis‐mannose conjugate 3 might be governed by at least two factors: first, destabilization of aromatic stacking in 1 and second, by carbohydrate‐aromatic amino acid and/or carbohydrate‐carbohydrate interactions . The latter interpretation was supported by FTIR analysis of 3 before and after aggregation, where the O–H stretching frequency shifted from 3384 to a more broadened peak at 3300 cm −1 , whereas the peak of O–H bending in COOH also shifted from 1455 to a more broad peak at 1421 cm ‐1 , suggesting the presence of hydrogen bonding network in self‐assembled 3 .…”

Section: Resultsmentioning

confidence: 91%

“…A solution of acetylated Lys bismannose (1 g, 1.09 mmol) in dry DCM (20 ml) and DMF (10 ml) was cooled to 0 °C, and 1‐hydroxybenzotriazole (0.16 g, 1.18 mmol) was added, followed by dicyclohexylcarbodimide (0.25 g, 1.21 mmol). After 1 h, TFA salt of Phe‐Phe methyl ester (0.51 g, 1.15 mmol) was added to the reaction mixture, followed by triethylamine (0.2 ml, 1.42 mmol).…”

Section: Methodsmentioning

confidence: 99%

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Controlling morphology of peptide‐based soft structures by covalent modifications

Gour

Barman

Verma

2012

Journal of Peptide Science

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Control of gross morphology of soft matter remains an area of continued interest. Towards this goal, this paper describes conjugation of mannose residues and introduction of thiol functionalities to diphenylalanine (FF) dipeptide, a fibrillating motif from amyloid-β peptide, as covalent modifiers of its solution-phase self-assembly process. It was found that covalent attachment of a single mannose residue to FF leads to the retention of tubular structures, whereas the conjugation of two mannose units, linked through a Lys residue, resulted in a dramatic change from tubular morphology to spherical structures. However, a similar switch to spherical objects could be achieved by introducing a thiol residue in the mono-mannosylated FF dipeptide. Interestingly, these glycopeptides also exhibited interaction with concanavalin A, thereby providing an indirect evidence for the availability of mannose units for the process of lectin-carbohydrate interaction in the self-organized state.

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Section: Resultsmentioning

confidence: 91%

Section: Methodsmentioning

confidence: 99%

Controlling morphology of peptide‐based soft structures by covalent modifications

Gour

Barman

Verma

2012

Journal of Peptide Science

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“…Template-free methods also avoid problems such as shell collapse and pore contamination during template removal [33][34][35] . Although self-templating has been the major recipe for the synthesis of metal oxide and metal sulfide-based hollow spheres [32][33][34] , this method has been less explored to synthesize organic and polymer-based hollow spheres [35][36][37] . The hollow spherical COF (DhaTab), reported in this paper, consists of a macroporous inner cavity (pore width 0.5-2 mm) wrapped up by the mesoporous COF shell (width 20-40 nm).…”

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confidence: 99%

Self-templated chemically stable hollow spherical covalent organic framework

et al. 2015

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Covalent organic frameworks are a family of crystalline porous materials with promising applications. Although active research on the design and synthesis of covalent organic frameworks has been ongoing for almost a decade, the mechanisms of formation of covalent organic frameworks crystallites remain poorly understood. Here we report the synthesis of a hollow spherical covalent organic framework with mesoporous walls in a single-step template-free method. A detailed time-dependent study of hollow sphere formation reveals that an inside-out Ostwald ripening process is responsible for the hollow sphere formation. The synthesized covalent organic framework hollow spheres are highly porous (surface area B1,500 m 2 g À 1 ), crystalline and chemically stable, due to the presence of strong intramolecular hydrogen bonding. These mesoporous hollow sphere covalent organic frameworks are used for a trypsin immobilization study, which shows an uptake of 15.5 mmol g À 1 of trypsin.

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“…The perbenzylated dimannosyl-lysine 6 ( Figure 3A) was synthesized by a slightly modified previously reported procedure (Gour et al, 2009). The perbenzylated dimannosyl-lysine 6 was conjugated with commercially available DSPE-PEG-NH 2 in the presence of EDC • HCl and sulfo-NHS.…”

Section: Synthesis Of Dimannosyl-peg-dspe Derivative Man 2 -Lys-peg-mentioning

confidence: 99%

Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery

Štimac

Cvitaš

Frkanec

et al. 2016

International Journal of Pharmaceutics

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Mannosylated self-assembled structures for molecular confinement and gene delivery applications

Cited by 14 publications

References 30 publications

Controlling morphology of peptide‐based soft structures by covalent modifications

Controlling morphology of peptide‐based soft structures by covalent modifications

Self-templated chemically stable hollow spherical covalent organic framework

Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery

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