Imine Based Self-Healing Hydrogel Triggered by Periodate

2020 ◽  
Author(s):  
Alexis Wolfel ◽  
Cecilia Inés Alvarez Igarzabal ◽  
Marcelo Ricardo Romero
Keyword(s):  
Functional Groups ◽  
Time Window ◽  
Crosslinking Reaction ◽  
Self Healing ◽  
Swelling Properties ◽  
Covalent Bonds ◽  
Smart Systems ◽  
Primary Amino ◽  
Vicinal Diols ◽  
Aldehyde Groups

<p>Design of materials with novel sensitivities and smart behaviour is important for the development of smart systems with automated responsiveness. We have recently reported the synthesis of hydrogels, cross-linked by <i>N,N'</i>-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating valuable a-oxo-aldehyde functional groups, useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from <a>2-aminoethyl methacrylate </a>hydrochloride (AEMA), coexisting with DAT into the same network. The a-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.</p>

scholarly journals Imine Based Self-Healing Hydrogel Triggered by Periodate

2020 ◽  
Author(s):  
Alexis Wolfel ◽  
Cecilia Inés Alvarez Igarzabal ◽  
Marcelo Ricardo Romero
Keyword(s):  
Functional Groups ◽  
Time Window ◽  
Crosslinking Reaction ◽  
Self Healing ◽  
Swelling Properties ◽  
Covalent Bonds ◽  
Smart Systems ◽  
Primary Amino ◽  
Vicinal Diols ◽  
Aldehyde Groups

<p>Design of materials with novel sensitivities and smart behaviour is important for the development of smart systems with automated responsiveness. We have recently reported the synthesis of hydrogels, cross-linked by <i>N,N'</i>-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating valuable a-oxo-aldehyde functional groups, useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from <a>2-aminoethyl methacrylate </a>hydrochloride (AEMA), coexisting with DAT into the same network. The a-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.</p>

scholarly journals BODIPY based self-healing fluorescent gel formation via acylhydrazone linkage

RSC Advances ◽  
2016 ◽  
Vol 6 (13) ◽  
pp. 10601-10605 ◽  
Author(s):  
Tugba Ozdemir ◽  
Fazli Sozmen
Keyword(s):  
Functional Groups ◽  
Gel Formation ◽  
Self Healing ◽  
Covalent Bonds ◽  
Reversible Formation

Polymeric BODIPY derivatives with reactive functional groups undergo reversible formation of covalent bonds leading to self-healing properties.

scholarly journals Biohydrogel Based on Dynamic Covalent Bonds for Wound Healing Applications

2021 ◽  
Vol 11 (15) ◽  
pp. 6945
Author(s):  
Chukwuma O. Agubata ◽  
Cynthia C. Mbaoji ◽  
Ifeanyi T. Nzekwe ◽  
César Saldías ◽  
David Díaz Díaz
Keyword(s):  
Wound Healing ◽  
Interfacial Tension ◽  
Blood Clotting ◽  
Phenylboronic Acid ◽  
Moisture Loss ◽  
Self Healing ◽  
Covalent Bonds ◽  
Treatment Groups ◽  
Acid Soluble Collagen ◽  
Thixotropic Behavior

In this work, a biohydrogel based on alginate and dynamic covalent B-O bonds, and derived composites, has been evaluated for wound healing applications. In particular, a phenylboronic acid–alginate (PBA-Alg) complex was synthesized by coupling 3-aminophenylboronic acid onto alginate, and used to prepare varied concentrations of hydrogels and silicate-based nanocomposites in PBS. The resulting hydrogels were characterized in terms of interfacial tension, moisture uptake and loss, interaction with fresh acid-soluble collagen, self-healing ability, effects on blood clotting and wound healing. The interfacial tension between the hydrogels and biorelevant fluids was low and moisture loss of 55%–60% was evident without uptake from the environment. The components of the hydrogels and their mixtures with collagen were found to be compatible. These hydrogels showed efficient self-healing and thixotropic behavior, and the animals in the treatment groups displayed blood clotting times between 9.1 min and 10.7 min. In contrast, the composites showed much longer or shorter clotting times depending on the silicate content. A significant improvement in wound healing was observed in 3% w/v PBA-Alg formulations. Overall, the PBA-Alg hydrogels exhibit self-healing dynamic covalent interactions and may be useful in dressings for incision wounds.

scholarly journals Nonsurgical treatment of skin cancer with local delivery of bioadhesive nanoparticles

2021 ◽  
Vol 118 (7) ◽  
pp. e2020575118
Author(s):  
Jamie K. Hu ◽  
Hee-Won Suh ◽  
Munibah Qureshi ◽  
Julia M. Lewis ◽  
Sharon Yaqoob ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Surgical Excision ◽  
Tumor Burden ◽  
Nonsurgical Treatment ◽  
Matrix Proteins ◽  
Poly Lactic Acid ◽  
Covalent Bonds ◽  
Cpg Oligodeoxynucleotides ◽  
Skin Cancers ◽  
Vicinal Diols

Keratinocyte-derived carcinomas, including squamous cell carcinoma (SCC), comprise the most common malignancies. Surgical excision is the therapeutic standard but is not always clinically feasible, and currently available alternatives are limited to superficial tumors. To address the need for a nonsurgical treatment for nodular skin cancers like SCC, we developed a bioadhesive nanoparticle (BNP) drug delivery system composed of biodegradable polymer, poly(lactic acid)-hyperbranched polyglycerol (PLA-HPG), encapsulating camptothecin (CPT). Nanoparticles (NPs) of PLA-HPG are nonadhesive NPs (NNPs), which are stealthy in their native state, but we have previously shown that conversion of the vicinal diols of HPG to aldehydes conferred NPs the ability to form strong covalent bonds with amine-rich surfaces. Herein, we show that these BNPs have significantly enhanced binding to SCC tumor cell surfaces and matrix proteins, thereby significantly enhancing the therapeutic efficacy of intratumoral drug delivery. Tumor injection of BNP-CPT resulted in tumor retention of CPT at ∼50% at 10 d postinjection, while CPT was undetectable in NNP-CPT or free (intralipid) CPT-injected tumors at that time. BNP-CPT also significantly reduced tumor burden, with a portion (∼20%) of BNP-CPT–treated established tumors showing histologic cure. Larger, more fully established PDV SCC tumors treated with a combination of BNP-CPT and immunostimulating CpG oligodeoxynucleotides exhibited enhanced survival relative to controls, revealing the potential for BNP delivery to be used along with local tumor immunotherapy. Taken together, these results indicate that percutaneous delivery of a chemotherapeutic agent via BNPs, with or without adjuvant immunostimulation, represents a viable, nonsurgical alternative for treating cutaneous malignancy.

Oxidative cyclization for the synthesis of complex tetrahydrofuran-containing natural products

2013 ◽  
Vol 85 (6) ◽  
pp. 1175-1184 ◽  
Author(s):  
Robert D. C. Pullin ◽  
Radosław M. Lipiński ◽  
Timothy J. Donohoe
Keyword(s):  
Natural Products ◽  
Amino Acid ◽  
Functional Groups ◽  
Lewis Acid ◽  
Excitatory Amino Acid ◽  
Oxidative Cyclization ◽  
Annonaceous Acetogenins ◽  
Hydride Shift ◽  
Vicinal Diols ◽  
Shift Sequence

The osmium-catalyzed oxidative cyclization of vicinal diols onto proximal olefins to generate 2,5-cis-substituted tetrahydrofurans (THFs) has been exploited as the key step for the construction of several complex THF-containing natural products, namely, the annonaceous acetogenins cis-sylvaticin, sylvaticin, and the excitatory amino acid neo-dysiherbaine A. Recently modified conditions that employ a Lewis acid enable the cyclization to proceed under milder conditions, providing greater tolerance to acid-sensitive functional groups, as demonstrated in two of the syntheses. Flexibility for the construction of 2,5-trans-THFs was demonstrated in the synthesis of sylvaticin by utilization of an intramolecular hydride-shift sequence.

Self-Healing Polymers Based on Reversible Covalent Bonds

2015 ◽  
pp. 1-58 ◽  
Author(s):  
Natascha Kuhl ◽  
Stefan Bode ◽  
Martin D. Hager ◽  
Ulrich S. Schubert
Keyword(s):  
Self Healing ◽  
Covalent Bonds ◽  
Reversible Covalent

Polyacrolein microspheres as a new tool in cell biology

1982 ◽  
Vol 56 (1) ◽  
pp. 157-175
Author(s):  
S. Margel ◽  
U. Beitler ◽  
M. Ofarim
Keyword(s):  
Cell Biology ◽  
Polymerization Process ◽  
Amino Groups ◽  
Ph Values ◽  
Human Red Blood Cells ◽  
Primary Amino ◽  
Aldehyde Groups ◽  
Potential Use ◽  
Specific Labelling ◽  
Reactive Aldehyde

Polyacrolein (PA) microspheres in sizes ranging from 0.04 micron to 40 microns were synthesized. Magnetic and fluorescent PA microspheres were formed by carrying out the polymerization process in the presence of appropriate ferrofluidic or fluorochromic compounds, respectively. The microspheres carry reactive aldehyde groups, through which various ligands, containing primary amino groups, were covalently bound at physiological pH values. The potential use of these microspheres was demonstrated by the specific labelling of fresh human red blood cells (RBC) and by the separation of human RBC from turkey RBC by means of a magnetic field. PA microspheres were also bound covalently to the anti-allergic drug disodium chromoglycate (DSCG) and the conjugate was used for the labelling of rat basophilic leukaemia cells.

2. The fundamentals

2017 ◽  
pp. 6-24
Author(s):  
Graham Patrick
Keyword(s):  
Functional Groups ◽  
Atomic Number ◽  
Outer Shell ◽  
Intramolecular Interactions ◽  
Covalent Bonds ◽  
Linear Chains ◽  
Element Carbon ◽  
Carbon Carbon Bonds ◽  
Valence Electrons ◽  
Branched Chains

‘The fundamentals’ investigates why the element carbon is so suited for the generation of so many compounds. Carbon has atomic number six, meaning it has six protons in its nucleus and six electrons around the nucleus, four of which are valence electrons held in the outer shell. Carbon achieves a stable, full outer shell of electrons by sharing electrons with other elements and other carbon atoms to form covalent bonds. The carbon–carbon bonds are one of the principle reasons why so many organic molecules are possible, including linear chains, branched chains, and rings. The naming of compounds and identification of structures is also explained along with stereochemistry, functional groups, and intermolecular and intramolecular interactions.

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