Vapor-based synthesis of maleimide-functionalized coating for biointerface engineering

Tsai, Meng-Shiun; Lin, Ching-Fuh; Huang, Chi-Hui; Gu, Jiun-An; Huang, Sheng‐Tung; Yu, Jihong; Chen, Hsien‐Yeh

doi:10.1039/c2cc35892a

Cited by 36 publications

(37 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is advantageous in that CVD coatings are more stable than the SAMs of alkanethiols commonly used with μCP. In fact, μCP has been exploited in combination with CVD to generate spatioselective sensing platforms (79), to coimmobilize multiple biologically active ligands (80), and to spatio-selectively control cell adhesion and growth (81). For example, sufficiently thin (on the order of a few nanometers) CVD coatings were polymerized onto surface plasmon resonance (SPR) chips to facilitate the spatio-selective patterning of biotin-hydrazide moieties to create a sensing array (79).…”

Section: Soft Lithographymentioning

confidence: 99%

Current Trends and Challenges in Biointerfaces Science and Engineering

Ross

Lahann²

2015

Annu. Rev. Chem. Biomol. Eng.

View full text Add to dashboard Cite

The cellular microenvironment is extremely complex, and a plethora of materials and methods have been employed to mimic its properties in vitro. In particular, scientists and engineers have taken an interdisciplinary approach in their creation of synthetic biointerfaces that replicate chemical and physical aspects of the cellular microenvironment. Here the focus is on the use of synthetic materials or a combination of synthetic and biological ligands to recapitulate the defined surface chemistries, microstructure, and function of the cellular microenvironment for a myriad of biomedical applications. Specifically, strategies for altering the surface of these environments using self-assembled monolayers, polymer coatings, and their combination with patterned biological ligands are explored. Furthermore, methods for augmenting an important physical property of the cellular microenvironment, topography, are highlighted, and the advantages and disadvantages of these approaches are discussed. Finally, the progress of materials for prolonged stem cell culture, a key component in the translation of stem cell therapeutics for clinical use, is featured.

show abstract

Section: Soft Lithographymentioning

confidence: 99%

Current Trends and Challenges in Biointerfaces Science and Engineering

Ross

Lahann²

2015

Annu. Rev. Chem. Biomol. Eng.

View full text Add to dashboard Cite

show abstract

“…The maleimide Mal=Gly 1 was obtained by condensation of malic anhydride (10) with Gly in refluxing acetic acid. 25,26 Chiral amino acids are expected to show significant racemization under these reaction conditions.…”

Section: Synthesis Of the Mal=gly And Mal=d-xaa Building Blocksmentioning

confidence: 99%

“…The formation of succinimide thioethers via thiol 1,4‐addition is frequently used to form bioconjugates or to immobilize bioactive compounds on surfaces . It is the preferred method for the formation of antibody‐drug conjugates .…”

Section: Introductionmentioning

confidence: 99%

“…The formation of succinimide thioethers via thiol 1,4-addition is frequently used to form bioconjugates or to immobilize bioactive compounds on surfaces. [1][2][3][4][5][6][7][8][9][10][11][12] It is the preferred method for the formation of antibody-drug conjugates. 5,13 Yet, only few studies are dedicated to the construction of homogeneous bioconjugates which do not exist as mixtures of diastereomers at the ligation site.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The stereodynamics of macrocyclic succinimide‐thioethers

Lenz

Horx

Geyer

2018

Journal of Peptide Science

View full text Add to dashboard Cite

Maleimide-thiol coupling is a popular bioconjugation strategy, but little is known about the stereoselectivity and the stereodynamics of the succinimide thioether formed in a biopolymer environment. We used thiol 1,4-addition for the macrocyclisation of 5 designed pentapeptides with the ringsize of hexapeptides because they incorporate the succinimide thioether (4-8). Both succinimide diastereomers are observed in the constrained macrocyclic rings in each case. In spite of the low diastereoselectivity of the macrocyclisation reaction, there is a significant influence of the amino acid environment on the epimerization rate of the succinimide. Its half life can be as short as several hours at room temperature when Gly is the amino acid following the succinimide (peptide 8). On the contrary, no epimerization is detectable even after several weeks in the case of d-Phe C-terminal to the succinimide in peptide 4. Already the small selection of examples shows how big the differences in epimerization rates can be and that the local environment has a significant influence. The variation of amino acids in the vicinity of the ligation site points the way towards the synthesis of bioconjugates which are obtained as stable and separable diastereomers.

show abstract

“…The classical thiol‐ene or thiol‐yne reactions are highly useful bioconjugation reactions with the benefit of their tolerance to water and oxygen, though they usually need be photochemically or thermally activated . Similarly, maleimide‐thiol reactions can proceed under a milder reaction condition more compatible with delicate biomolecules, with an ideal reaction pH range of 6.5–7.5.…”

Section: Common Bioactive Surface Functionalization Reactionsmentioning

confidence: 99%

Orthogonal surface functionalization through bioactive vapor‐based polymer coatings

Deng

Lahann

2014

J of Applied Polymer Sci

View full text Add to dashboard Cite

REVIEWSABSTRACT: Reactive chemical vapor deposition (CVD) polymerization provides a substrate-independent platform for effective functionalization of virtually any solid substrates, flat, or curved, even with complex geometries. This article reviews bioactive surface functionalization strategies based on CVD polymerization and highlights commonly used surface chemistries. These reactions include alkyne-azide "click" chemistry, reactions of active esters with amine, aldehydes/ketones with hydrazides and alkoxyamines, thiols with alkenes and alkynes and surface-initiated atom transfer radical polymerization. The resulting biofunctional surface coatings can facilitate orthogonal immobilization of more than one type of ligand on a substrate. CVD polymer coatings with nanoscale thicknesses are widely applicable in biomedical applications and can be easily integrated into micro-and nanodevice fabrication.

show abstract

Vapor-based synthesis of maleimide-functionalized coating for biointerface engineering

Cited by 36 publications

References 27 publications

Current Trends and Challenges in Biointerfaces Science and Engineering

Current Trends and Challenges in Biointerfaces Science and Engineering

The stereodynamics of macrocyclic succinimide‐thioethers

Orthogonal surface functionalization through bioactive vapor‐based polymer coatings

Contact Info

Product

Resources

About