PEG — A versatile conjugating ligand for drugs and drug delivery systems

Kolate, Atul; Baradia, Dipesh; Patil, Sushilkumar; Vhora, Imran; Kore, Girish; Misra, Ambikanandan

doi:10.1016/j.jconrel.2014.06.046

Cited by 524 publications

(352 citation statements)

References 153 publications

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“…As pristine Jeffamine does not possess any group for a UV detector, it was derivatized by dansyl chloride prior to the HPLC analysis. As previously reported, multiple peaks from the oligomeric mixture were identified for Jeffamine-(dansyl) 2 (Figure 2, red line). 25 In spite of the complex pattern of the mixed-oligomeric structure, the peaks from monofunctionalized Jeffamine clearly can be observed, as shifted from those of the original dansylcoupled Jeffamine (Figure 2, blue line).…”

Section: Resultssupporting

confidence: 80%

“…The retention time of the Fmoc-Jeffamine-dansyl was delayed by ca. 1.5 min compared with Jeffamine-(dansyl) 2 .…”

Section: Resultsmentioning

confidence: 98%

“…[1][2][3] It has been reported that PEGylation improves the quality of various kinds of materials used for biomedical application in such way of increasing protein/peptide stability, promoting efficient drug delivery, and increasing biocompatibility toward nonfouling medical devices. [4][5][6][7] Versatile functional groups at the terminal sites of PEG polymers enable the attachment of various biomolecules such as proteins, nucleic acids, and carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

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Efficient Synthesis and Characterization of Monoprotected Symmetrical Poly(Ethylene Glycol) Diamine

Jeong

Youn

Nam

et al. 2017

Bulletin Korean Chem Soc

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Solid-phase synthesis of monoprotected poly(ethylene glycol) (PEG) diamine is demonstrated. 2-Chlorotrityl chloride (2-CTC) resin was used as a solid support for inducing monofunctionalization using excess PEG diamine. Fmoc-monoprotected PEG was prepared from 2-CTC resin and fully characterized by high-performance liquid chromatography and electrospray ionization mass spectrometry. We envision that this strategy will provide an efficient method of preparing various kinds of heterobifunctional PEG molecules without a need for further purification steps.

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Section: Resultssupporting

confidence: 80%

“…The retention time of the Fmoc-Jeffamine-dansyl was delayed by ca. 1.5 min compared with Jeffamine-(dansyl) 2 .…”

Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Efficient Synthesis and Characterization of Monoprotected Symmetrical Poly(Ethylene Glycol) Diamine

Jeong

Youn

Nam

et al. 2017

Bulletin Korean Chem Soc

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“…Poly‐ethylene glycol (PEG) is an uncharged chemical polymer with broad application in biotechnology, biophysics, nanotechnology and biomedical research, not only as a common precipitant for proteins1 and nucleic acids2 but also for hydrophilic coating of particles or surfaces, preparation of hydrogels3 and, in particular, for conjugation to biopharmaceuticals 4, 5. Prominent features of PEG are its strong hydrophilicity, its disordered conformation in a dissolved state, which causes an expanded hydrodynamic volume as well as “crowding effect,” the availability in a variety of average sizes and its largely inert chemical and biological behavior 6…”

Section: Introductionmentioning

confidence: 99%

The polypeptide biophysics of proline/alanine‐rich sequences (PAS): Recombinant biopolymers with PEG‐like properties

Breibeck

Skerra

2017

Biopolymers

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PAS polypeptides comprise long repetitive sequences of the small L‐amino acids proline, alanine and/or serine that were developed to expand the hydrodynamic volume of conjugated pharmaceuticals and prolong their plasma half‐life by retarding kidney filtration. Here, we have characterized the polymer properties both of the free polypeptides and in fusion with the biopharmaceutical IL‐1Ra. Data from size exclusion chromatography, dynamic light scattering, circular dichroism spectroscopy and quantification of hydrodynamic and polar properties demonstrate that the biosynthetic PAS polypeptides exhibit random coil behavior in aqueous solution astonishingly similar to the chemical polymer poly‐ethylene glycol (PEG). The solvent‐exposed PAS peptide groups, in the absence of secondary structure, account for strong hydrophilicity, with negligible contribution by the Ser side chains. Notably, PAS polypeptides exceed PEG of comparable molecular mass in hydrophilicity and hydrodynamic volume while exhibiting lower viscosity. Their uniform monodisperse composition as genetically encoded polymers and their biological nature, offering biodegradability, render PAS polypeptides a promising PEG mimetic for biopharmaceutical applications.

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“…However, the ideal promoiety remains to be chosen. Poly(ethylene glycol) chains are a strong candidate: their presence can increase aqueous solubility of hydrophobic drugs, prolong circulation time, slow down hydrolysis, and increase stability in the gastrointestinal tract [48][49][50][51][52][53]. This type of decoration is particularly valuable for protein/polypeptide drugs and drug-carrying liposomes (rev.s, e.g., [54][55][56][57][58][59]), which can be protected from phagocytosis and are less at risk of provoking an immune response.…”

Section: Introductionmentioning

confidence: 99%

N-Monosubstituted Methoxy-oligo(ethylene glycol) Carbamate Ester Prodrugs of Resveratrol

et al. 2015

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Abstract:Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3-[OCH2CH2]n-) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption.

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PEG — A versatile conjugating ligand for drugs and drug delivery systems

Cited by 524 publications

References 153 publications

Efficient Synthesis and Characterization of Monoprotected Symmetrical Poly(Ethylene Glycol) Diamine

Efficient Synthesis and Characterization of Monoprotected Symmetrical Poly(Ethylene Glycol) Diamine

The polypeptide biophysics of proline/alanine‐rich sequences (PAS): Recombinant biopolymers with PEG‐like properties

N-Monosubstituted Methoxy-oligo(ethylene glycol) Carbamate Ester Prodrugs of Resveratrol

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