Jeremy A. Boomer's research while affiliated with Purdue University and other places

... Several studies combining the more recent ether lipids derivatives with diverse antineoplastic agents provide clinically significant benefits [99]. Shin et al. [102] described the synthetic pathway applied to the synthesis of 1-O-1′-(Z) -hexadecenyl-2-O-methyl-rac-glycero-3phosphocholine, the Z-vinyl ether analogue of ET-18-OMe, which shows significant antitumor activity in pancreatic tumor cells. Also, Bittman et al. [103] reported the incorporation of a cis-O-vinyl linkage into the sn-1 position of glycerol of plasmalogens to synthesize a new antitumor ether lipid analogue of ET-18-OCH 3 . ...

... For example, it has been shown that liposomal uptake by rat alveolar macrophages was enhanced by inclusion of O-steroyl amylopectin and maleylated bovine serum albumin ( Vyas et al., 2004) or mannose ( Wijagkanalan et al., 2008) in the bilayer. Acid-catalyzed hydrolysis of vinyl ethers has been used to induce the degradation of liposomes ( Boomer et al., 2003). The relative stability of liposomes is an advantage during circulation, but is also a detriment: As noted, while effective drug carriers protect their cargo and must therefore remain stable in circulation, they need eventually to release the encapsulated drug in a predetermined way. ...

... Singlet oxygen has a concise life of 10 −5 s, and it is a strong oxidant that can oxidize cellular constituents such as proteins, lipids, and nucleic acids [29]. The diffusion distance of 1 O 2 is short but has sufficient energy to react at any site within a 100 nm liposome, as reported by Gerasimov et al. [30]. Anderson and Thompson first reported drug release from liposomes using photo-induced oxidation [31] in 1992. ...

... As shown in Figs. 2 and 3, substantial AS014 was efficiently internalized into the cells via the interaction between SPG and Dectin-1. Multiple complexes would be contained in an endosomal vesicle and account for a considerable portion of endosomal vesicles, leading to a change in osmotic pressure by a depletion effect [41]. Subsequently, the collapse of endosomal vesicles would be induced, resulting in an influx of most AS014 into the cytoplasmic compartment. ...

... Chiral metal-coordinated supramolecular assemblies have recently received much attention and are among the most promising structures in supramolecular chemistry, 1-10 because metal-coordinated systems play essential roles in the formation of superstructures such as coiled-coil helix bundle proteins, 11,12 DNA superhelices, 13 and protein-DNA hybrid superstructures. 14,15 Thus, better understanding of emergent chiral phenomena and the origin of chirality at the supramolecular level are essential for biomedical applications such as drug delivery, [16][17][18] gene delivery, 19 tissue engineering, 20,21 imaging, 22 and sensing. 23,24 Self-sorting is one of the high-delity self-recognitions or self-discriminations in living systems, in which a complex object is recognizable from non-self into well-organized supramolecular architectures. ...

... Our initial attempt of the synthesis of 1 (a) and alternative synthetic plan for PlsEtn-[16:0/18:1 n-9] (b). Byun and Bittman 1999;Shin et al. 2001;Shin, Gerasimov and Thompson 2002;Shin and Thompson 2003;Van den Bossche, Shin and Thompson 2007). In this article, we describe a new synthesis of a plasmenylethanolamine via a one-pot phosphite esterification-oxidation sequence to construct the ethanolamine phosphonate moiety, which would also be applicable to the synthesis of many other PlsEtn molecular species. ...

... These results are similar to previous reports where an increase in the length of the spacer segment resulted in reduced cytotoxicity in vitro [46]. Moreover, lipid-containing carbamate bonds have lower cytotoxicity, are stable under neutral conditions, and are prone to hydrolysis at low pH (in the endosome) [47][48][49]. The increased cytotoxicity exhibited by the PEGylated lipoplexes was proposed to be due to a higher cationic lipid concentration [50] and the possibility that these lipids generate reactive oxygen species (ROS). ...

... PCp is a plasmalogen, which is a naturally occurring phospholipid that has a vinyl ether fatty alcohol attached to the glycerol backbone at the sn-1 position (Naudí et al., 2015). Plasmalogens are commonly found in the cell membranes of electrically active tissues such as brain, heart, and myelin (Thompson et al., 2004). Also, immune cells, such as leukocytes, neutrophils, and macrophages, contain significant levels of plasmalogens (Nagan and Zoeller, 2001). ...