Catechol and Gallol derivatives-based nano/bio medical technology using non-covalent bonds

Abstract

gallol-containing monomer). First, TA forms DNA hydrogels by reversibly connecting phosphodiester bonds. Second, TA forms medicinal glue with poly(ethylene glycol) via hydrogen bonds. The glue exhibits esophageal mucoadhesive properties. Third, the stoichiometric ratio for TA/protein complex and their in vivo motion are demonstrated. The TA/protein complex shows in vivo stealth effect exhibiting long circulation time. Especially, the complex adheres to heart by high affinity of TA to the extracellular matrix protein, elastin. The forth part (Chapter 5) represents gallol-rich hydrogels via multiple hydrogen bonds between gallol-conjugated hyaluronic acid and oligomerized epigallocatechin gallate (gallol-tethered polymers). The exterior many gallol groups out of the gels efficiently capture enzyme, which results in prohibiting completely cancer cell invasion.

Recently, tissue adhesive materials have been developed using mussel-inspired chemistry originated from 3, 4-dihydroxy-L-phenylalanine (DOPA). Marine mussels tightly attach to all types of inorganic and organic wet surfaces by secreting thread-like adhesive pads, these functional groups of which are useful for preparing medicinal adhesive materials. Furthermore, gallol-containing compounds found in various plants are available for designing biomaterials. Although numerous chemical bonds, covalent crosslinking (catechol/catechol and catechol/amine or thiol groups) and non-covalent reversible bonds, exist in catechol/gallol chemistry, few studies have focused on the design of biomaterials using the only reversible, non-covalent bonds. Therefore, in this Ph D. thesis, the intermolecular interactions of catechol/gallol derivatives with other natural/synthetic polymers will be used for the development of nano/bio medical technology. The first part (Chapter 2) provides the intermolecular interactions of dopamine (catechol-containing monomer), with emulsifying polymers (i.e., poly(vinyl alcohol) or pluronics) for preparation of poly(D, L-lactic-co-glycolic acid) microparticles and poly(caprolactone) for electrospun tissue scaffolds. The second part (Chapter 3) provides bloodless needles prepared by reversible hydrogen bonds and covalent crosslinking of catechol-tethered chitosan. The third part (Chapter 4) shows drug-encapsulated formulations utilizing intermolecular interactions of tannic acid (TA