Probing the Dye Chemistry of Genipin-Based Temporary Tattoos Using a Self-Assembled Monolayer Skin Mimic

Inkbox是多伦多的一家公司，它将世界上第一个为期两周的纹身商业化。这项技术不仅具有观赏性的应用，而且在医疗应用方面也有令人兴奋的潜力。这项技术的关键在于一种活性成分，它来自一种名为京尼平的水果提取物，以前曾被用作组织工程和材料科学的无毒交联剂。当京尼平应用于皮肤，它转化成一个充满活力的蓝色。虽然这种转变背后的化学原理还不清楚，但据信它通过与氨基酸反应与皮肤结合，然后经过进一步的低聚反应形成纹身的鲜艳蓝色。在本提案中，我们将使用合成的“皮肤模拟物”来更好地理解在受控条件下的反应过程。我们的皮肤模拟物将包含一层附着在固体表面的分子，这层分子可以进行先进的光谱分析。我们将结合京尼平皮肤模拟和研究其反应性，使用光谱数据来建立结合以及随后的反应，导致墨水盒纹身的蓝色。这些研究将帮助Inkbox优化其配方，以增强皮肤渗透性并延长纹身寿命，并提供有关分子间相互作用如何改变产品颜色的见解。

Inkbox is a company in Toronto that has commercialized the world's first two-week tattoo. This technology hasornamental applications, as well as exciting potential in medical applications. The key to this technology in anactive ingredient derived from a fruit extract called Genipin, which has previously been explored as a non-toxiccrosslinking reagent for tissue engineering and materials science. When Genipin is applied to the skin, ittransforms into a vibrant blue colour. Although the chemistry behind this transformation is not wellunderstood, it is believed to bind to the skin by reacting with amino acids, and then undergo furtheroligomerization reactions to form the vibrant blue colour of the tattoo. In this proposal, we will use a synthetic"skin mimic" to acquire a better understanding of this reaction process under controlled conditions. Our skinmimic will comprise a layer of molecules adhered to a solid surface that is amenable to advanced spectroscopicanalysis. We will bind Genipin to the skin mimic and study its reactivity, using spectroscopic data to establishthe binding as well as the subsequent reactions that cause the blue colouration of Inkbox tattoos. These studieswill help Inkbox optimize its formulation to enhance skin penetration and increase tattoo longevity, and alsoprovide insight into how intermolecular interactions may be able to alter the colouration of the product.