Tuning the response of a pH-sensitive membrane switch

Thomas, James L.; You, Hong; Tirrell, David A.

doi:10.1021/ja00115a039

Cited by 87 publications

(85 citation statements)

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“…Hydrogel systems are of great interest for drug delivery because they circumvent the need for a surgical incision, in particular when they can respond to external stimuli such as pH and temperature. [4][5][6] Hydrogels are usually formed by a hydrophilic polymer matrix cross-linked chemically through covalent bonds or physically through hydrogen bonds, crystallized domains, or hydrophobic interactions. [1] Copolymers composed of polyester and polyether blocks are increasingly considered as worthwhile degradable materials, especially in the field of parenteral drug delivery.…”

Section: Introductionmentioning

confidence: 99%

Bioresorbable Hydrogels Prepared Through Stereocomplexation between Poly(L‐lactide) and Poly(D‐lactide) Blocks Attached to Poly(ethylene glycol)

Li¹

2003

Macromolecular Bioscience

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Block copolymers were synthesized by ring‐opening polymerization of L‐lactide or D‐lactide in the presence of mono‐ or dihydroxyl poly(ethylene glycol), using zinc metal as catalyst. The resulting copolymers were characterized by various techniques, namely 1H NMR spectroscopy, differential scanning calorimetry (DSC), X‐ray diffractometry, and Raman spectrometry. The composition of the copolymers was designed such that they were water soluble. Bioresorbable hydrogels were prepared from aqueous solutions containing both poly(L‐lactide)/poly(ethylene glycol) and poly(D‐lactide)/poly(ethylene glycol) block copolymers. Rheological studies confirmed the formation of hydrogels resulting from stereocomplexation between poly(L‐lactide) and poly(D‐lactide) blocks.

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Section: Introductionmentioning

confidence: 99%

Bioresorbable Hydrogels Prepared Through Stereocomplexation between Poly(L‐lactide) and Poly(D‐lactide) Blocks Attached to Poly(ethylene glycol)

Li¹

2003

Macromolecular Bioscience

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“…A range of biocompatible synthetic polymers, either neutral or charged, have also been studied with regard to their role in imparting structural stability to liposomes (7). Several recent studies have demonstrated that the polymer coatings may not only play a passive protective role, but may in fact participate in the drug release process by responding to some external stimulus (8). We (9-1 1) and others (12,13) have explored the use of hydrophobically modified poly-(N-isopropylacrylamides) (HM-PNIPAM) as liposome stabilizers.…”

Section: Introductionmentioning

confidence: 99%

Pyrene-labeled amphiphilic poly-(N-isopropylacrylamides) prepared by using a lipophilic radical initiator: synthesis, solution properties in water, and interactions with liposomes

Winnik¹,

Adronov²,

Kitano³

1995

Can. J. Chem.

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Fluorescently labeled amphiphilic poly-(N-isopropylacrylamides) (PNIPAM) substituted with a N-[4-(I-pyrenyl)butyl]-N-n-octadecyl group at the chain end were prepared by free-radical polymerization in dioxane of N-isopropylacrylamide (NIPAM) using 4,4'-azobis(4-cyano-N,N-[4-(I -pyrenyl)butyl]-noctadecy1)pentanamide as the initiator. The solution properties of the polymers in water were studied as a function of polymer concentration and temperature. Quasi-elastic light-scattering measurements and fluorescence experiments monitoring the pyrene excimer and pyrene monomer emissions revealed the presence of multimolecular polymeric micelles below the lower critical solution temperature (LCST) of PNIPAM. These underwent partial, reversible reorganization as they were heated above the LCST. The interactions of the pyrene-labeled amphiphilic PNIPAM with dimyristoylphosphatidylcholine (DMPC) liposomes have been examined in water at 25OC. From fluorescence experiments it was established that the polymeric micelles are disrupted irreversibly upon contact with the liposomes. The anchoring of the polymer chains occurs by insertion of their hydrophobic tail within the phospholipidic bilayer, as evidenced from a large decrease of the pyrene excimer emission relative to pyrene monomer emission. The copolymers remained anchored within the bilayer as the temperature of the copolymer--1iposome suspension was raised above the LCST of PNIPAM.

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“…[3,6,7] Thus, the vinyl polymers poly(a-methylacrylic acid), poly(a-ethylacrylic acid), and poly(a-propylacrylic acid) undergo conformational change at progressively higher pH values, corresponding to increase endosomal membrane lysis activity. [8][9][10][11][12] Eccleston et al [13][14][15] described a biodegradable, metabolitederived polyamide, poly(L-lysine iso-phthalamide), with a hydrophobic backbone and pendant carboxyl groups. Despite lacking hydrophobic side chains presented in fusogenic peptides and poly(a-alkylacrylic acid)s, poly(L-lysine iso-phthalamide) displays a pH-dependent conformational change [16][17][18] and weak cell-membrane lytic capacity over a low pH range (pH 4.6-5.0).…”

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confidence: 99%

Synthetic pH‐Responsive Polymers for Protein Transduction

et al. 2009

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A pH‐responsive, endosomal membrane disruptive, metabolite‐derived polyamide PP‐75 is developed to deliver the MBP‐Apoptin fusion protein, which induces tumor‐specific apoptosis into human osteogenic sarcoma Saos‐2 cells. The intracellular distribution and colocalization of MBP‐Apoptin‐AF647 (MA‐AF649) and PP‐75‐FITC provide strong evidence that PP‐75 both enhances uptake and facilitates cytoplasmic release of MBP‐Apoptin.

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Tuning the response of a pH-sensitive membrane switch

Cited by 87 publications

References 0 publications

Bioresorbable Hydrogels Prepared Through Stereocomplexation between Poly(L‐lactide) and Poly(D‐lactide) Blocks Attached to Poly(ethylene glycol)

Bioresorbable Hydrogels Prepared Through Stereocomplexation between Poly(L‐lactide) and Poly(D‐lactide) Blocks Attached to Poly(ethylene glycol)

Pyrene-labeled amphiphilic poly-(N-isopropylacrylamides) prepared by using a lipophilic radical initiator: synthesis, solution properties in water, and interactions with liposomes

Synthetic pH‐Responsive Polymers for Protein Transduction

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