Patra Soumen, Kar Sukhendu, Gopal Bag Braja
Department of Chemistry & Chemical Technology, Vidyasagar University, Midnapore, West Bengal, 721102, India.
Chem Asian J. 2024 Dec 16;19(24):e202400361. doi: 10.1002/asia.202400361. Epub 2024 Nov 7.
Bixin 1 is the major constituent of the reddish carotenoids present in the seed-coat of Bixa orellana. The use of the extract of the seed-coat of Bixa orellana in food, cosmetics and garments is well known. The nano-sized long 24 C chain molecule has nine conjugated double bonds having extended conjugation with the '-COOH' and '-COOMe' groups present at the two ends of the molecule. Herein, we report the first self-assembly of bixin in several aqueous liquids. The molecule undergoes spontaneous self-assembly in several liquids yielding vesicular self-assembly. Characterizations of the self-assemblies of bixin were carried out by various microscopic techniques, X-ray diffraction and FTIR studies. The critical vesicular concentrations (CVCs) of the compound carried out in DMSO-water in three different solvent ratios as 2: 1 (v/v), 1: 1 (v/v) and 1: 4 (v/v) were determined to be 100 μM, 90 μM and 60 μM respectively indicating lower CVC values at higher proportion of water. Utilization of the vesicular self-assemblies of bixin have been demonstrated in the entrapment and release of fluorophores including the anticancer drugs doxorubicin and curcumin. Self-assembled bixin and curcumin loaded self-assembled bixin showed significant antibacterial activity with both Gram positive as well as Gram negative bacteria.
胭脂树橙1是红木槿种皮中存在的红色类胡萝卜素的主要成分。红木槿种皮提取物在食品、化妆品和服装中的应用广为人知。这种纳米级的长24碳链分子有九个共轭双键，与分子两端的“-COOH”和“-COOMe”基团存在延伸共轭。在此，我们报道了胭脂树橙在几种水性液体中的首次自组装。该分子在几种液体中自发自组装，形成囊泡自组装。通过各种显微镜技术、X射线衍射和傅里叶变换红外光谱研究对胭脂树橙的自组装进行了表征。在二甲基亚砜-水体系中，以2:1（v/v）、1:1（v/v）和1:4（v/v）三种不同溶剂比例测定该化合物的临界囊泡浓度（CVC），分别为100μM、90μM和60μM，表明在水比例较高时CVC值较低。已证明胭脂树橙的囊泡自组装可用于包裹和释放包括抗癌药物阿霉素和姜黄素在内的荧光团。自组装的胭脂树橙以及负载姜黄素的自组装胭脂树橙对革兰氏阳性菌和革兰氏阴性菌均表现出显著的抗菌活性。
