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Related Concept Videos

Phosphodiester Linkages01:01

Phosphodiester Linkages

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Overview
Phosphodiester bond forms when a phosphoric acid molecule (H3PO4) links with two hydroxyl groups (–OH) of two other molecules, forming two ester bonds. Two water molecules are released in this process. The phosphodiester bond is commonly found in nucleic acids (DNA and RNA) and plays a critical role in their structure and function.
Phosphodiester Bonds Link Nucleotides Together
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Ligand Binding and Linkage00:49

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Allosteric proteins have more than one ligand binding site; the binding of a ligand to any of these sites influences the binding of ligands to the other sites. When a protein is allosteric, its binding sites are called coupled or linked.  In the case of enzymes, the site that binds to the substrate is known as the active site and the other site is known as the regulatory site. When a ligand binds to the regulatory site, this leads to conformational changes in the protein that can influence...
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Preparation and Reactions of Thiols02:33

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Structure and Nomenclature of Thiols and Sulfides02:17

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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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Nuclear Stability

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Protons and neutrons, collectively called nucleons, are packed together tightly in a nucleus. With a radius of about 10−15 meters, a nucleus is quite small compared to the radius of the entire atom, which is about 10−10 meters. Nuclei are extremely dense compared to bulk matter, averaging 1.8 × 1014 grams per cubic centimeter. If the earth’s density were equal to the average nuclear density, the earth’s radius would be only about 200 meters.
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Related Experiment Video

Updated: Jan 24, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Linkage Groups within Thiol-Ene Photoclickable PEG Hydrogels Control In Vivo Stability.

Michael D Hunckler1, Juan D Medina2, Maria M Coronel1

  • 1Woodruff School of Mechanical Engineering and Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, 315 Ferst Dr. NW, Atlanta, GA, 30332, USA.

Advanced Healthcare Materials
|May 22, 2019
PubMed
Summary

Amide-linked poly(ethylene glycol) (PEG) hydrogels offer improved in vivo stability compared to ester-linked versions. This advancement enhances their potential for long-term biomedical applications like cell delivery and regenerative medicine.

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biomaterialscell encapsulationhydrogelsphotochemistrypoly(ethylene glycol)

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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Regenerative Medicine

Background:

  • Thiol-norbornene (thiol-ene) photoclickable poly(ethylene glycol) (PEG) hydrogels are widely used in vitro for cell encapsulation and drug delivery.
  • Existing ester-linked PEG-norbornene (PEG-4eNB) hydrogels exhibit excellent cytocompatibility but rapid in vivo degradation within 24 hours.
  • This rapid degradation limits their utility in in vivo biomedical applications.

Purpose of the Study:

  • To investigate the in vivo stability of PEG-4eNB hydrogels.
  • To develop a modified PEG hydrogel with improved in vivo longevity.
  • To compare the properties of amide-linked PEG-norbornene (PEG-4aNB) hydrogels with existing PEG-4eNB hydrogels.

Main Methods:

  • Synthesis of 4-arm amide-linked PEG-norbornene (PEG-4aNB) hydrogels.
  • In vivo degradation studies in subcutaneous and intraperitoneal environments.
  • Assessment of mechanical properties, crosslinking kinetics, and cytocompatibility with rat islets and human mesenchymal stem cells.
  • Comparison of PEG-4aNB hydrogels against PEG-4eNB hydrogels.

Main Results:

  • PEG-4eNB hydrogels with nondegradable crosslinkers degraded rapidly in vivo within 24 hours.
  • PEG-4aNB hydrogels demonstrated long-term in vivo stability, persisting for months.
  • PEG-4aNB hydrogels exhibited equivalent mechanical properties, crosslinking kinetics, and cytocompatibility to PEG-4eNB hydrogels.
  • No significant differences in cytocompatibility were observed between PEG-4aNB and PEG-4eNB hydrogels.

Conclusions:

  • Replacing ester linkages with amide linkages in PEG-norbornene hydrogels significantly enhances their in vivo stability.
  • PEG-4aNB hydrogels present a promising alternative biomaterial for in vivo applications requiring long-term integrity.
  • The PEG-4aNB platform offers a viable replacement for PEG-4eNB hydrogels without compromising essential properties or requiring major design modifications.