《Selective Delivery of Dicarboxylates to Mitochondria by Conjugation to a Lipophilic Cation via a Cleavable Linker》 was published in Molecular Pharmaceutics in 2020. These research results belong to Prag, Hiran A.; Kula-Alwar, Duvaraka; Pala, Laura; Caldwell, Stuart T.; Beach, Timothy E.; James, Andrew M.; Saeb-Parsy, Kourosh; Krieg, Thomas; Hartley, Richard C.; Murphy, Michael P.. Computed Properties of C3H7BrO The article mentions the following:
Many mitochondrial metabolites and bioactive mols. contain two carboxylic acid moieties that make them unable to cross biol. membranes. Hence, there is considerable interest in facilitating the uptake of these mols. into cells and mitochondria to modify or report on their function. Conjugation to the triphenylphosphonium (TPP) lipophilic cation is widely used to deliver mols. selectively to mitochondria in response to the membrane potential. However, permanent attachment to the cation can disrupt the biol. function of small dicarboxylates. Here, we have developed a strategy using TPP to release dicarboxylates selectively within mitochondria. For this, the dicarboxylate is attached to a TPP compound via a single ester bond, which is then cleaved by intramitochondrial esterase activity, releasing the dicarboxylate within the organelle. Leaving the second carboxylic acid free also means mitochondrial uptake is dependent on the pH gradient across the inner membrane. To assess this strategy, we synthesized a range of TPP monoesters of the model dicarboxylate, malonate. We then tested their mitochondrial accumulation and ability to deliver malonate to isolated mitochondria and to cells, in vitro and in vivo. A TPP-malonate monoester compound, TPP11-malonate, in which the dicarboxylate group was attached to the TPP compound via a hydrophobic undecyl link, was most effective at releasing malonate within mitochondria in cells and in vivo. Therefore, we have developed a TPP-monoester platform that enables the selective release of bioactive dicarboxylates within mitochondria. In addition to this study using 3-Bromopropan-1-ol, there are many other studies that have used 3-Bromopropan-1-ol(cas: 627-18-9Computed Properties of C3H7BrO) was used in this study.
3-Bromopropan-1-ol(cas: 627-18-9) was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and molten salt-polymers. Furthermore, it was used in the synthesis of chiral, quaternary prolines via cyclization of quaternary amino acids.Computed Properties of C3H7BrO
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