ArticleInternational journal of molecular sciences2020
On the Mechanism of Genipin Binding to Primary Amines in Lactose-Modified Chitosan at Neutral pH.
Article in International journal of molecular sciences, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 30 citations in OpenAlex.
- Perspectives on the pH-Influenced Design of Chitosan-Genipin Nanogels for Cell-Targeted Delivery.Pharmaceutics · 2025Article
- Efficient siRNA delivery to murine melanoma cellsNanoscale advances · 2024Article
- Genipin's potential as an anti-cancer agent: from phytochemical origins to clinical prospects.Medical oncology (Northwood, London, England) · 2024Review
- Article
- Eco-friendly synthesis of chitosan and its medical application: from chitin extraction to nanoparticle preparation.ADMET & DMPK · 2023Review
- Review
- Influence of Temperature and Polymer Concentration on the Nonlinear Response of Highly Acetylated Chitosan-Genipin Hydrogels.Gels (Basel, Switzerland) · 2022Article
- Histological, Biomechanical, and Biological Properties of Genipin-Crosslinked Decellularized Peripheral Nerves.International journal of molecular sciences · 2021Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
The present manuscript deals with the elucidation of the mechanism of genipin binding by primary amines at neutral pH. UV-VIS and CD measurements both in the presence of oxygen and in oxygen-depleted conditions, combined with computational analyses, led to propose a novel mechanism for the formation of genipin derivatives. The indications collected with chiral and achiral primary amines allowed interpreting the genipin binding to a lactose-modified chitosan (CTL or Chitlac), which is soluble at all pH values. Two types of reaction and their kinetics were found in the presence of oxygen: (i) an interchain reticulation, which involves two genipin molecules and two polysaccharide chains, and (ii) a binding of one genipin molecule to the polymer chain without chain-chain reticulation. The latter evolves in additional interchain cross-links, leading to the formation of the well-known blue iridoid-derivatives.
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Registered trials
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