3,3'-dithiobis(propionohydrazide)

• CAS: 50906-77-9
• Catalog Number: ACM50906779
• Category: Main Products
• Molecular Weight: 238.33
• Molecular Formula: C6H14N4O2S2
• Synonyms: 4,5-dithia-octanedioic acid dihydrazide
• Appearance: White solid

Case Study

3,3'-Dithiobis(propionohydrazide) as a Redox-Responsive Crosslinker for Intelligent Hydrogels

Zhang, Renyi, et al. Polymers for Advanced Technologies 28.12 (2017): 1759-1763.

Design of intelligent, stimuli-responsive biomaterials is highly desired for advanced biomedical applications, such as controlled drug delivery and tissue engineering. This work investigated the use of 3,3'-dithiobis(propionohydrazide) (DTP) as a dynamic crosslinker to construct redox-responsive hydrogels with oxidized hyaluronic acid (oxi-HA).
Synthesis Design: Use DTP as a bifunctional hydrazide crosslinker: two hydrazide termini of DTP react with aldehyde groups of oxi-HA via Schiff-base/hydrazone chemistry to form a hydrogel network at physiological pH. The central disulfide moiety in DTP renders the crosslinks cleavable upon treatment with reducing agents (e.g. dithiothreitol, DTT) and the hydrogel thus becomes responsive to redox stimuli. The mechanical and degradation properties could be tuned by varying the concentrations of oxi-HA and DTP (4-6 wt% each).
Key Performance:
· All prepared hydrogels exhibited good rheological characteristics, a high equilibrium swelling ratio, and a slow degradation rate under normal physiological (PBS) conditions. The hydrogel formulated with 5 wt% oxi-HA and 6 wt% DTP (oxi-HA5/DTP6) showed superior comprehensive performance among the tested variants.
· Stimuli-Responsive Drug Release: In vitro release studies with a model protein (Bovine Serum Albumin) confirmed sustained release in PBS. This release profile was expedited in a reducing medium containing DTT, demonstrating on-demand release capability.

Leveraging 3,3'-Dithiobis(propionohydrazide) to Develop High-Strength, Self-Healing Polyurethane Elastomers

Wang, Yubin, et al. Journal of Polymer Science 62.22 (2024): 5149-5158.

Materials that seamlessly combine durability with the ability to autonomously repair damage under mild conditions are highly sought after for industrial applications. This study examined a strategic approach to address this challenge by incorporating 3,3'-dithiobis(propionohydrazide) as a dual-functional monomer, introducing synergistic dynamic bonds into a polyurethane matrix.
Strategy: 3,3'-dithiobis(propionohydrazide) was reacted with an isocyanate-terminated polyurethane prepolymer (Pre-PU). This reaction ingeniously integrates two types of dynamic covalent bonds into the polymer network: acylsemicarbazide (ASC) bonds and, inherent to the monomer's structure, disulfide (S-S) bonds. This dual dynamic bond system is the key to the material's unique properties.
Key Results: The resulted ASC-SS-PU elastomer exhibited a high tensile strength of 17.1 MPa, significant stretchability (735% elongation), and high toughness (57.16 MJ/m3). The material demonstrated remarkable self-healing efficiency. Samples with a breakage rate exceeding 90% could achieve over 70% healing after being treated at a moderate temperature of 60°C for only 40 minutes. This healing performance is notably superior to that of conventional ASC-based polyurethane elastomers lacking the synergistic disulfide bonds.