Comparison of metal free polymer–dye conjugation strategies in protic solvents

Gaitzsch, Jens; Delahaye, Maarten; Poma, Alessandro; Prez, Filip Du; Battaglia, Giuseppe

doi:10.1039/c6py00518g

Cited by 20 publications

(18 citation statements)

References 51 publications

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“…The protected maleimide initiator (Mal-Br) was prepared according to a previously published procedure [46]. ATRP synthesis and purification of P(OEG 10 MA) 20 -PDPA 90 from ME-Br, Rho-Br and Mal-Br initiators was carried out as previously described [35,47]. The copolymer composition was analyzed by 1H NMR in CDCl 3 and the polydispersity was determined by size exclusion chromatography in acidic water (0.25 vol% TFA in water).…”

Section: Methodsmentioning

confidence: 99%

iRGD peptide conjugation potentiates intraperitoneal tumor delivery of paclitaxel with polymersomes

et al. 2016

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Polymersomes are versatile nanoscale vesicles that can be used for cytoplasmic delivery of payloads. Recently, we demonstrated that pH-sensitive polymersomes exhibit an intrinsic selectivity towards intraperitoneal tumor lesions. A tumor homing peptide, iRGD, harbors a cryptic C-end Rule (CendR) motif that is responsible for neuropilin-1 (NRP-1) binding and for triggering extravasation and tumor penetration of the peptide. iRGD functionalization increases tumor selectivity and therapeutic efficacy of systemic drug-loaded nanoparticles in many tumor models. Here we studied whether intraperitoneally administered paclitaxel-loaded iRGD-polymersomes show improved efficacy in the treatment of peritoneal carcinomatosis. First, we demonstrated that the pH-sensitive polymersomes functionalized with RPARPAR (a prototypic CendR peptide) or iRGD internalize in the cells that express NRP-1, and that internalized polymersomes release their cargo inside the cytosol. CendR-targeted polymersomes loaded with paclitaxel were more cytotoxic on NRP-1-positive cells than on NRP-1-negative cells. In mice bearing peritoneal tumors of gastric (MKN-45P) or colon (CT26) origin, intraperitoneally administered RPARPAR and iRGD-polymersomes showed higher tumor-selective accumulation and penetration than untargeted polymersomes. Finally, iRGD-polymersomes loaded with paclitaxel showed improved efficacy in peritoneal tumor growth inhibition and in suppression of local dissemination compared to the pristine paclitaxel-polymersomes or Abraxane. Our study demonstrates that iRGD-functionalization improves efficacy of paclitaxel-polymersomes for intraperitoneal treatment of peritoneal carcinomatosis.

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Section: Methodsmentioning

confidence: 99%

iRGD peptide conjugation potentiates intraperitoneal tumor delivery of paclitaxel with polymersomes

et al. 2016

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“…In another study in 2016 by Xu et al, maleimide‐containing tannic acid (TAMA) as a new surface anchor was introduced to functionalize stainless steel with maleimide moieties and examine the efficiency of Michael addition of TAMA with thiol‐containing compounds . Also, in 2016, Gaitzsch et al discussed and compared different metal‐free conjugation reactions (such as thiol/maleimide conjugation) to functionalize an amphiphilic block copolymer with dyes for improved imaging in optical microscopy . Recently, in an interesting study, Aktan et al fabricated multifunctional nanogels that contain maleimide as well as thiol groups.…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

Dadfar

Sekula-Neuner

Trouillet

et al. 2018

Adv Materials Inter

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Two quick and efficient, metal catalyst free conjugation routes for the covalent attachment of functional compounds to functionalized surfaces by scanning probe lithography methods are compared in the presented work. The studied methods are thiol‐yne coupling (TYC) and thiol‐ene Michael addition (TEMA). First, the surface of hydroxyl‐terminated glass is thiolated using (3‐mercaptopropyl)trimethoxysilane (MPTMS). Then, in the distinct experiments, the thiol‐terminated surface is spotted by microchannel cantilever spotting with different fluorescent and nonfluorescent inks containing cycloalkyne (dibenzocyclooctyne (DBCO)) or alkene (maleimide) groups. Experiments with different fluorophores show that both routes are successful in coupling functional moieties to the surface in a short time and low temperature. Comparing the protein binding experiments for biotin‐DBCO and biotin‐maleimide reveals a higher surface density of immobilized biotin via the TEMA route. The results from this study are applicable in design and fabricating of biosensors, appropriate for protein detection and other biomedical/biological applications.

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“…In a particular case, the so called polymerisation-induced self-assembly (or PISA) [169], supramolecular assemblies can be obtained directly during polymerisation in high concentrations (up to 25% w/v solids), thus compatibly with large-scale production [152][153][154][169][170][171][172][173][174][175][176][177][178]. Despite their popularity, supramolecular biomaterials obtained by polymers made via ATRP and RAFT suffer from a purification drawback, which might encumber their safety [141][142][143][144] and/or the patient compliance for therapeutic applications due to the exhibition of a certain colour or odour in the final product [145,146]. From this point of view, nitroxide-mediated polymerisation (NMP) deserves to be mentioned [149].…”

Section: Mixed Polymerisationmentioning

confidence: 99%

Molecular bionics – engineering biomaterials at the molecular level using biological principles

et al. 2019

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Life and biological units are the result of the supramolecular arrangement of many different types of molecules, all of them combined with exquisite precision to achieve specific functions. Taking inspiration from the design principles of nature allows engineering more efficient and compatible biomaterials. Indeed, bionic (from bion-, unit of life and -ic, like) materials have gained increasing attention in the last decades due to their ability to mimic some of the characteristics of nature systems, such as dynamism, selectivity, or signalling. However, there are still many challenges when it comes to their interaction with the human body, which hinder their further clinical development. Here we review some of the recent progress in the field of molecular bionics with the final aim of providing with design rules to ensure their stability in biological media as well as to engineer novel functionalities which enable navigating the human body.

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Comparison of metal free polymer–dye conjugation strategies in protic solvents

Cited by 20 publications

References 51 publications

iRGD peptide conjugation potentiates intraperitoneal tumor delivery of paclitaxel with polymersomes

iRGD peptide conjugation potentiates intraperitoneal tumor delivery of paclitaxel with polymersomes

A Comparative Study of Thiol‐Terminated Surface Modification by Click Reactions: Thiol‐yne Coupling versus Thiol‐ene Michael Addition

Molecular bionics – engineering biomaterials at the molecular level using biological principles

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