Disease relevance of Butyl Group

• This work indicates that the relatively high native concentration of + (large KW), which has commonly been thought to lead to the occurrence of acid-catalyzed reactions in HTW without added catalyst, does not explain the dehydration of 1,4-butanediol in HTW without catalyst [1].
• BACKGROUND: Toxicity of 1,4-butanediol, an industrial solvent and a substance of abuse, is still misunderstood and not well documented [2].
• 1,4-Butanediol (1,4-BD), a prodrug converted in vivo to gamma-hydroxybutyric acid by alcohol dehydrogenase, has resulted in life-threatening overdoses and deaths [3].
• We conclude that GHB, GBL, and 1,4-BD protect against rat focal cerebral ischemia from transient MCAO [4].
• In transient MCAO, the mean volume of infarction for control rats was 464.4 +/- 17.9 cu.mm versus 273.6 +/- 53.1, 233.3 +/- 44.7, and 275.4 +/- 39.9 cu.mm for rats treated with 1,4-BD (P < 0.05), GBL (P < 0.05), and GHB (P < 0.05), respectively [4].

Psychiatry related information on Butyl Group

• In contrast, 1,4-BD at 50 mg/kg stimulated locomotor activity without producing any depression of activity [5].
• gamma-Hydroxybutyratic acid (GHB), and its prodrugs 4-butyrolactone and 1,4-butanediol, represent expanding drugs of abuse, although GHB is also used therapeutically to treat narcolepsy and alcoholism [6].

High impact information on Butyl Group

• Clinical Pharmacology of 1,4-Butanediol and Gamma-hydroxybutyrate After Oral 1,4-Butanediol Administration to Healthy Volunteers [7].
• Monolithic materials were prepared in capillaries by in situ polymerization of acrylamide, glycidyl methacrylate, and N,N'-methylenebisacrylamide in the presence of 1,4-butanediol, dodecanol, and DMSO as porogens [8].
• In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond [9].
• 1,4-Butanediol also enhanced PAP activity but markedly inhibited EAP activity [10].
• These data suggest that GBL and 1,4-BD are not metabolically converted to GHB in the brain, that enhanced brain penetration cannot account for potency differences between compounds, and that baclofen, like GHB, can readily cross the blood-brain barrier [11].

Chemical compound and disease context of Butyl Group

• Kinetics and mechanism of tetrahydrofuran synthesis via 1,4-butanediol dehydration in high-temperature water [1].
• Therefore, we speculate that 1,4-BD overdose toxicity can be prevented or attenuated with the ADH enzyme inhibitor 4-methylpyrazole (4-MP) as well as with CGP-35348 and NCS-382, novel high-affinity receptor antagonists of GABA(B) receptors and GHB receptors, respectively [12].

Biological context of Butyl Group

• We have studied the hydrolysis and synthesis reactions of the peptide bond involved in N-Cbz-L-tryptophanyl-glycineamide as catalyzed by alpha-chymotrypsin in various mixtures of water and 1,4-butanediol [13].
• In contrast to its depressant effects on schedule-controlled responding, 1,4-butanediol increased mean arterial pressure and heart rate; these increases were attenuated by ethanol [14].
• In the presence of 1,4-butanediol, alpha-chymotrypsin also catalyzed the esterification reaction between this diol and N-Cbz-L-tryptophan; this ester hydrolysis/synthesis reaction has thus also been examined [15].
• Their biotransformation by rat liver post-mitochondrial fraction into 1,4-butanediol and 1,5-pentanediol, respectively, is evaluated by determining these ultimate metabolites with a sensitive and suitable method [16].
• Here, we report dose-response and time-course analyses for effects of GBL and 1,4-BD on locomotor activity and body temperature in Swiss-Webster mice [5].

Anatomical context of Butyl Group

• Accordingly 1,4-butanediol, unlike GHB, failed to displace [(3)H]GHB and [(3)H]baclofen in brain membranes [17].
• A simple GC method for determination of cryoprotector diols 1,4-butanediol or 2,3-butanediol in isolated rat hepatocytes [18].
• We examined the potential neuroprotective effect of GHB and its chemical precursors, gamma-butyrolactone (GBL) and 1,4-butanediol (1,4-BD), in the rodent ischemic stroke model by intraluminal filament middle cerebral artery occlusion (MCAO) [4].
• To further delineate this distribution these enzymes were studied in testes from rats treated with Busulfan (the methane sulfonic acid diester of 1,4-butanediol), which causes degeneration of spermatogonia but not Sertoli cells [19].

Associations of Butyl Group with other chemical compounds

• We have investigated the interaction of 1,4 butanediol (1,4 BD) with ethanol and the involvement of the major metabolite of 1,4 BD, gamma-hydroxybutyric acid (GHB) in the ability of 1,4 BD to produce behavioral and EEG changes in rat as well as the toxic side effects of 1,4 BD [20].
• Intracerebroventricular (i.c.v.) administration of GABA, putrescine, and 1,4-butanediol all produced significant elevations in brain GHB, but GABA-T inhibitors blocked this effect of GABA and putrescine [21].
• Further alcohol dehydrogenase inhibitors, 4-methylpyrazole and ethanol, totally prevented the sedative/hypnotic effect of 1,4-butanediol; the aldehyde dehydrogenase inhibitor disulfiram partially blocked the sedative/hypnotic effect of 1,4-butanediol [17].
• The polymerization mixture consisting of 17.8% of BMA, 21.8% of EDMA, 18.0% of 1,4-butanediol, 42.0% of 1-propanol and 0.4% AIBN generated monolithic columns of the best performance having a sufficient permeability and the lowest separation impedance [22].
• An air-stable titanium-organic framework, prepared from Ti(O(i)Pr)(4) and 1,4-butanediol, has been characterized via single-crystal X-ray diffraction, revealing a unique supramolecular structure [23].

Gene context of Butyl Group

• METHODS: We investigated this possibility by flow cytometric analysis of membrane glycoproteins (GPs) Ib and IIb/IIIa and the activation markers CD62P and CD63 in platelet concentrates (PCs) prepared from whole blood that was held for either 6 h without cooling plates (n = 20) or for 24 h on cooling plates of 1,4-butanediol (n = 20) [24].
• A related increase in tissue 1,4-BD concentration supported the hypothesis of an in vivo competition of the two substances for alcohol dehydrogenase [25].
• Here we show that in vivo injection of 1,4-butanediol into adult Drosophila leads to GHB synthesis (GHB was detectable 5 min after 1,4-butanediol injection and increased dramatically 1-2 h later) [26].
• The mixed macrodiols were reacted with 4,4'-methylenediphenyl diisocyanate (MDI) and 1,4-butanediol (BDO) chain extender [27].
• CD-1 mice were overdosed with 1,4-BD, 600 mg/kg i.p. Mice then received 4-MP, 25 mg/kg i.p., or control injections after 1 min, 5 min, and symptom appearance [3].

Analytical, diagnostic and therapeutic context of Butyl Group

• Poly(ether ester amide) (PEEA) copolymers based on poly(ethylene glycol) (PEG), 1,4-butanediol and dimethyl-7,12-diaza-6,13-dione-1,18-octadecanedioate were evaluated as scaffold materials for tissue engineering [28].
• Pretreatment with 4-MP also increased the TD(50) of 1,4-BD for the rotarod test from 163 mg/kg (95% CI, 136-196 mg/kg) in control mice to 4,900 mg/kg (95% CI, 4,812-4,989 mg/kg) in pretreated mice [29].
• A severe withdrawal syndrome from GHB, 1,4-BD and GBL has been increasingly documented over the last years, necessitating the development of a reliable animal model for investigations of potential therapeutic approaches [30].
• Laboratory diagnosis of 1,4-BD and GHB overdose by routine urine organic acid analysis [31].
• Two organic solvents, phenol and 1,4-butanediol, were used as additives to facilitate the crystallization of free rTxln-1 [32].

References