Supramolecular Structures of Novel Carbohydrate-Based Phospholipids

Hird, Geoffrey S.; McIntosh, and Thomas J.; Grinstaff, Mark W.

doi:10.1021/ja001653i

Cited by 17 publications

(10 citation statements)

References 23 publications

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“…[1][2][3][4][5][6] Conventional glycerol-based phospholipids such as phosphatidylcholine (PC) and phosphatidylethanolamine (PE) can self-assemble into three-dimensional hollow spheres with self-closed structures in water known as liposomes. 7,8 Owing to their intrinsic biocompatibility and unique self-assembly behavior, phospholipids and liposomes have been widely applied in the elds of biotechnology, drug carriers, gene delivery, contrast agents, as well as the surface modication of biomaterials. [9][10][11][12][13] So far, several liposome-based drug delivery systems have been approved by the Food and Drug Administration (FDA) and numerous liposome-encapsulated agents have been used in clinical trials.…”

Section: Introductionmentioning

confidence: 99%

Supramolecularly engineered phospholipids constructed by nucleobase molecular recognition: upgraded generation of phospholipids for drug delivery

Wang

et al. 2015

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Supramolecularly engineered phospholipids constructed by nucleobase molecular recognition: upgraded generation of phospholipids for drug delivery

Wang

et al. 2015

Chem. Sci.

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“…We previously showed that the carbohydrate-based phospholipid, dilauroyl ribo-phosphocholine (DLRPC), possesses a greater phase-transition temperature and enthalpy, as compared to dilauroyl phosphocholine (DLPC) . In this study, we selected three chain lengths spanning from C 12 to C 20 to characterize and develop the structure−property relationships for this class of phospholipids.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Carbohydrate-Based Phospholipids

et al. 2002

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Novel carbohydrate-based phospholipids containing two saturated C(12) (dilauroyl ribo-phosphocholine) (DLRPC), C(14) (dimyristoyl ribo-phosphocholine) (DMRPC), and C(20) (diarachadonyl ribo-phosphocholine) (DARPC) carboxylic acid chains were synthesized. The physical properties of the supramolecular structures formed by these compounds were compared to those formed by their direct glycerol analogues dilauroyl phosphocholine (DLPC), dimyristoyl phosphocholine (DMPC), and diarachadonyl phosphocholine (DAPC). Modulated differential scanning calorimetry (MDSC) and X-ray diffraction data indicated that with chain lengths < or =14 carbons, the carbohydrate backbone increased the thermal stability of the bilayer below the phase-transition temperature (T(m)) as compared to the glycerol-based lipids. With longer chains (C(20)), the bilayer structure was destabilized as compared to glycerol-based lipids. NMR studies of a DMRPC vesicle dispersion reveal split choline headgroup signals and distinct magnetization transfer effects arising from the "inner" and "outer" surfaces of the bilayer vesicle. Modulated differential scanning calorimetry also demonstrated that glycerol- and carbohydrate-based lipids mix, as evidenced by a single intermediate T(m). In addition, carbohydrate-based lipid/cholesterol mixtures exhibited a decrease in enthalpy with an increase in cholesterol concentration. Unlike glycerol phospholipids, carbohydrate lipids were resistant to enzymatic degradation by phospholipase A(2) (PLA(2)).

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“…[3] Recently, the synthesis and physical characterization of novel carbohydrate-based phospholipids have been reported; these phospholipids self-assemble into liposome-like structures in aqueous solution. [4] An example is the synthesis and physicochemical study of one such uridine-based phospholipid. [5] The authors demonstrated that this modified phospholipid exhibits physical properties that differ from those of its glycerolbased analogues; this indicates the importance that the constitution of the backbone has for the nature of the bilayer structure.…”

Section: Introductionmentioning

confidence: 99%

“…Nucleoside phospholipids have one more structural element for molecular recognition-namely, the nucleobase-than carbohydrate phospholipids. [4,8] …”

Section: Introductionmentioning

confidence: 99%

Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

Choi

Jung

et al. 2005

ChemBioChem

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Phospholipids and liposomes have been the subjects of considerable attention because of their importance in biological systems. We have efficiently synthesized novel nucleoside-based phospholipids in six-step sequences starting from their corresponding nucleosides. These nucleoside-based phospholipids self-assemble into liposome-like structures in aqueous solutions. We have analyzed the structures of these liposomes by dynamic light scattering, transmission electron microscopy, and confocal microscopy.

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Supramolecular Structures of Novel Carbohydrate-Based Phospholipids

Cited by 17 publications

References 23 publications

Supramolecularly engineered phospholipids constructed by nucleobase molecular recognition: upgraded generation of phospholipids for drug delivery

Supramolecularly engineered phospholipids constructed by nucleobase molecular recognition: upgraded generation of phospholipids for drug delivery

Synthesis and Characterization of Carbohydrate-Based Phospholipids

Nucleoside‐Based Phospholipids and Their Liposomes Formed in Water

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