Disease relevance of trans isomer

• The substrate-binding site in Escherichia coli cyclophilin A preferably recognizes a cis-proline isomer or a highly distorted form of the trans isomer [1].
• In this study, we tested the role of the c-Jun N-terminal kinase (JNK) family of mitogen-activated protein kinases and their transcription factor target, c-Jun, in the cytotoxic response of small-cell lung cancer (SCLC) cells to cisplatin and its less effective trans-isomer, transplatin [2].
• Evaluation of 10-13 in the Lewis Lung carcinoma model indicated the bis(morpholinomethyl) analogue cis-13 to be antimetastatic, whereas the trans isomer 12 was toxic at a similar dose effecting a decrease in the life span of treated mice [3].
• Cisplatin, cis-[PtCl2(NH3)2], is commonly utilized in various combination chemotherapy protocols for the treatment of both ovarian and breast cancer while the corresponding trans isomer is therapeutically inactive [4].
• Plasma half-lives of the metabolites were 3.1 h (range 1.1-4.5 h) for the trans-isomer and 3.5 h (range 1.3-6.4 h) for the cis- isomer, and varied linearly with increasing patient body weight [5].

High impact information on trans isomer

• This EFE activity displays similar characteristics to EFE found in plant tissue: it converts the trans isomer of the ACC analogue 1-amino-2-ethylcyclopropane-1-carboxylic acid to 1-butene in preference to the cis isomer, and it is strongly inhibited by cobaltous ions and 1,10-phenanthroline [6].
• The trans-isomer of tubulozole (tubulozole-T, R 48 265), which has no antitumor activity in vivo, did not affect the microtubule system of cells in vitro or their capacity for directional migration or for malignant invasion [7].
• Modeling suggests steric hindrance at the active site as the determinant of the weak inhibiting potency of the trans isomer [8].
• The major cisplatin-damaged DNA-binding proteins of 26.5 and 28 kDa recognized adducts of DNA modified with cisplatin but not with its trans-isomer or with UV radiation [9].
• The bromo enol lactone trans isomer 2a was found to be a very effective inhibitor of HLE and chymotrypsin, as shown by the binding constants (KI), acylation rates (ka), inactivation rates, and partition ratios determined for each enzyme [10].

Chemical compound and disease context of trans isomer

• Prompted by the strong growth inhibitory activity of BCS (IC50; 0.03 microM) compared to its trans-isomer (IC50; 6.36 microM) and resveratrol (IC50; 33.0 microM) in cultured human lung cancer cells (A549), we investigated its mechanism of action [11].
• The subchronic toxicity of the trans isomer of N-(1,3,4,6,7-hexahydro-11bH-benzo[a] quinolizin-2-yl) propionanilide hydrochloride (TR2379), a new antihypertensive agent, was studied in rats and dogs [12].
• Solid and solution NMR studies of the complexation of Ag(+) with the trans isomer of captopril: Biological activities of this high blood pressure drug along with its Ag(+) complex [13].

Biological context of trans isomer

• 1H NMR time courses of the prolidase-catalyzed hydrolysis of L-alanyl-L-proline showed a faster removal of the trans isomer as the [enzyme]/[substrate] ratio was increased [14].
• In contrast, formation of 6 from 4 proceeds by general-base-catalyzed beta-elimination. trans-4-Hydroxycyclophosphamide undergoes ring opening ca. 4 times faster than the cis isomer, and cyclization of 4 favors the trans isomer by a factor of ca. 3 over the cis isomer [15].
• The trans isomer was found to be more effective for cell growth inhibition than its cis analogue both in the presence and in the absence of illumination [16].
• G-G base-pairing in nucleobase adducts of the anticancer drug cis-[PtCl2(NH3)(2-picoline)] and its trans isomer [17].
• Effects of a trans isomer of arachidonic acid on rat platelet aggregation and eicosanoid production [18].

Anatomical context of trans isomer

• The concentrations of the trans isomer in plasma and in breast milk were about 1/10 of those for the cis isomer [19].
• The interaction of calf thymus DNA with the antitumor drug cis-diamminedichloroplatinum(II), and with the clinically ineffective trans isomer, is studied by time-dependent fluorescence depolarization spectroscopy of intercalated ethidium [20].
• Despite spatial analogy between the trans isomer 5 and leucine-enkephalinamide, it possessed neither opioid agonist nor antagonist activity in the guinea pig ileal longitudinal muscle (GPI) or mouse vas deferens (MVD) preparations [21].
• It is shown that the tricyclic antidepressant drug doxepin (comprising 15% of the cis- and 85% of the trans-isomer) is a moderately potent competitive inhibitor of serotonin uptake in human blood platelets in vitro, with an inhibitory constant Ki of about 2 X 10(-7) M [22].
• Effects of the trans-isomer of 2-en-valproate (trans-2-en-NaVP; E-delta2-en-valproate or 2-en-valproate), an unsaturated metabolite of valproic acid (VPA), on intracellularly recorded sodium-dependent action potentials of cultured mouse spinal cord and cortical neurons were compared with those of the anticonvulsant sodium valproate (NaVP) [23].

Associations of trans isomer with other chemical compounds

• X-ray analysis of the trans isomer showed an axial disposition of the phenyl ring; however, NMR studies suggest that this conformation is fixed in the trans isomer, but not in the cis [24].
• It was found that N-(3-aminopropyl)-1,4-diamino-cis-but-2-ene [the cis isomer of the alkene analogue of spermidine] was a good substrate for spermine synthase, but that the trans isomer [N-(3-aminopropyl)-1,4-diamino-trans-but-2-ene] and the alkene analogue [N-(3-aminopropyl)-1,4-diaminobut-2-yne] were not substrates [25].
• Carbonyl ene cyclization of aldehydes 4a-e catalyzed by MeAlCl(2) in refluxing chloroform afforded the trans piperidines 7a-e with diastereomeric ratios of up to 93:7, while aldehyde 4f afforded solely the cis product 6f, which was resistant to isomerization to the trans isomer [26].
• We identified the zeatin isolated as the trans isomer by HPLC and by a radioimmunoassay in which monoclonal antibodies specific for trans-hydroxylated cytokinins were used [27].
• BACKGROUND: Cis-urocanic acid (cis-UCA), formed from the naturally occurring trans-isomer in the epidermis on ultraviolet (UV) radiation, initiates some of the changes leading to UV-induced immunosuppression, but its role in cutaneous carcinogenesis has not been fully investigated [28].

Gene context of trans isomer

• Despite trans isomer specificity of ERK2, a doubly phosphorylated RNase T1 was found as the final reaction product [29].
• However, in the case of 1-(cyclopropylmethyl)-N-n-propyl analogs, the trans isomer has a slightly higher 5-HT1A affinity than its cis counterpart [30].
• The trans isomer is able to form two good hydrogen bonds, with G13 on the same strand and A7 on the opposite strand [31].
• Compared to liposomes, DMPC in the complexes has more acyl chain trans isomers at temperatures above 24 degrees C; at temperatures above ca. 30 degrees C, trans isomer content is about the same for complexes and liposomes [32].
• The trans isomer was found to be more favorable than cis isomer by only 0.6 kcal/mol [33].

Analytical, diagnostic and therapeutic context of trans isomer

• High-performance liquid chromatography analysis showed that the mean peak level of the trans isomer was 5.7% that of the cis isomer [34].
• Resolution of cis and trans isomers by capillary column gas chromatography permitted assignment of the trans isomer to the C16:1 omega 7 acid [35].
• While selective crystallization schemes were developed to isolate the thermodynamically less stable trans isomer 2a, improved stereocontrol was subsequentially achieved by the application of ketene chemistry [36].
• X-Ray crystallography revealed that the 1,3-dioxane ring of the trans isomer 7 exists in the expected chair, "O-inside" conformation [37].
• 1. Transcerebral microdialysis was used to monitor dopamine, 3,4-dihydroxyphenylacetic acid (DOPAC), homovanillic acid (HVA) and trans-isomer of atypical neuroleptic drug carbidine concentrations in the dialysates from dorsal striatum of freely moving rats following i.p. administration of the drug at doses 0.5, 1,5 and 25 mg/kg [38].

References