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Targeting the Nervous System
Published in Nathan Keighley, Miraculous Medicines and the Chemistry of Drug Design, 2020
Binding to the adrenergic receptor involves the important function groups on catecholamine. Structure-activity relationships show the importance of the alcohol groups and the phenol catechol ring, as well as the ionised amine needed for binding roles in the receptor. The alcohol group is involved in hydrogen bonding; indicated by the R-enantiomer of noradrenaline being more active than the S-enantiomer. Compounds without the secondary alcohol group, for example dopamine, have greatly reduced activity, showing that the alcohol is important, but not essential for binding. The amine is normally ionised, being protonated at physiological pH, needed for ionic bonds to the Asp-113 anion in the receptor. Activity drops with substituents on the tertiary amine/quaternary salt.
Central Nervous System Effects of Essential Oil Compounds
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Elaine Elisabetsky, Domingos S. Nunes
Borneol 7 and isopulegol 8 (C10, monoterpenes) are α,β-saturated secondary alcohols presenting small, rigid, cyclic structures. Borneol 7 has a totally rigid structure with a small molecular volume (MV = 165.72), followed closely by myrtenol 1 (MV = 160.07) and isopulegol 8 (MV = 171.55) (Molinspiration, 2019). Molecules with higher or total rigidity are useful to reveal details of a given active site architecture, since a rigid structure does not adapt to the site by simple bonds twists. Totally rigid structures present only one conformation and are already in their minimum conformational energy, of special interest to structure-activity relationship studies because they may reveal precise information on the geometry of the active site to which they bind, with better chances of representing entirely new models for specific pharmacological activities.
Emollient Esters and Oils
Published in Randy Schueller, Perry Romanowski, Conditioning Agents for Hair and Skin, 2020
John Carson, Kevin F. Gallagher
The shortest of the branched short-chain alcohols is isopropyl alcohol (IPA). We have already discussed the properties of many of the esters of isopropyl alcohol (Table 6). One point to make is that IPA is a secondary alcohol as opposed to a primary alcohol. The esters of secondary alcohols are generally more stable to hydrolysis than the esters of primary alcohols. Therefore, one would expect to have formulations that are more stable with isopropyl myristate than if they were formulated with ethyl oleate. Indeed, IPM is used in many different formulations without significant hydorlysis and must therefore be considered as providing adequate stability for cosmetic formulation purposes.
Pharmacological strategies to reduce anthracycline-associated cardiotoxicity in cancer patients
Published in Expert Opinion on Pharmacotherapy, 2022
Anna Stansfeld, Utsav Radia, Caitriona Goggin, Preethika Mahalingam, Charlotte Benson, Andrea Napolitano, Robin L Jones, Stuart D Rosen, Vasilios Karavasilis
As discussed, the two-electron reduction by NADH dehydrogenase results in the formation of secondary alcohol metabolites, considered potentially causative in long-term anthracycline-associated cardiotoxicity [20]. The metabolites are commonly referred to as doxorubicinol (DOXOL), epirubicinol, daunorubicinol. This conversion occurs in the heart, and these metabolites accumulate and are not cleared as rapidly as anthracyclines. The resultant effect is that the increasing potency of the secondary alcohol metabolites cause greater cardiotoxicity than either the parent anthracycline drug, or the ROS. Proposed mechanisms for causing damage include the inactivation of calcium-channels and the interruption of iron homeostasis within a cell. The long-term accumulation of DOXOL, as opposed to doxorubicin, may indicate that the metabolite is the more toxic precipitant at a time beyond treatment completion when cardiotoxic events occur long after treatment is complete [21].
Effect of gal/GalNAc regioisomerism in galactosylated liposomes on asialoglycoprotein receptor-mediated hepatocyte-selective targeting in vivo
Published in Journal of Liposome Research, 2021
Hua Nie, Bo Qiu, Qi-Xuan Yang, Ying Zhao, Xiao-Min Liu, Ying-Ting Zhang, Fu-Lin Liao, Sheng-Yuan Zhang
Enzymatic esterification of the sugar is affected by steric hindrance around the hydroxyl group. Substitutions of the primary and secondary alcohols are remarkably distinguishable according to reports in the literature (Halldorsson et al.2001). Thus, in the cases of Gal, GalNAc, and Lac, the lipases showed outstanding selectivity for the hydroxyl group at the C-6′ position, but to no other positions. Furthermore, compared with other groups that reported mono-antennary Gal modified CHS derivative synthetic strategies, our synthetic method has only two steps (Scheme 2) and achieved a high yield of above 90%. On the other hand, Managit et al. (2005a) synthesized cholesten-5-yloxy-N-(4-((1-imino-2-d-thiogalactosylethyl) formamide via five steps. Wang et al. (2006) synthesized (5-Cholesten-3b-yl) 4-oxo-4-[2-(lactobionyl amido) ethylamido] butanoate via six steps, and Zhang et al. (2015) synthesized Gal-Polyethylene Glycol-Chol via nine steps. The level of complexity in these latter methods suggests there are significant industrial prospects for the enzymic method.
Co-processing of nateglinide with meglumine for enhanced dissolution rate: in vitro and in vivo evaluation
Published in Drug Development and Industrial Pharmacy, 2020
Alaa Y. Bazeed, Ebtessam A. Essa, Ahmed Nouh, Gamal M. El Maghraby
The FTIR spectrum of meglumine revealed absorption peaks at 3330 cm−1 which can be attributed to secondary amine stretching vibrations with the hydrogen bonded hydroxyl groups being noticed as a broad band in the range of 3200–3570 cm−1. The bending vibration of NH and OH was evident at 1630 cm−1 and 910 cm−1. The bands corresponding to in-plane bending of primary and secondary alcohol were noticed at 1298 cm−1 and 1238 cm−1. The C–N stretching was recorded at 1176 cm−1 with those of C–O being clear at 1049 cm−1, 1076 cm−1, and 1097 cm−1 for the primary and secondary alcohol (see the arrows in Figure 2). This spectrum is similar to the published data [21,22]. Dry grinding of meglumine did not alter the spectral pattern (Figure 2).