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Nitrocinnamoyl and chlorocinnamoyl derivatives of dihydrocodeinone: in vivo and in vitro characterization of mu-selective agonist and antagonist activity. (1/746)
Two 14beta-p-nitrocinnamoyl derivatives of dihydrocodeinone, 14beta-(p-nitrocinnamoylamino)-7,8-dihydrocodeinone (CACO) and N-cyclopropylmethylnor-14beta-(p-nitrocinnamoylamino)- 7, 8-dihydrocodeinone (N-CPM-CACO), and the corresponding chlorocinnamoylamino analogs, 14beta-(p-chlorocinnamoylamino)-7, 8-dihydrocodeinone (CAM) and N-cyclopropylmethylnor-14beta-(p-chlorocinnamoylamino) -7, 8-dihydrocodeinone (MC-CAM), were tested in opioid receptor binding assays and the mouse tail-flick test to characterize the opioid affinity, selectivity, and antinociceptive properties of these compounds. In competition binding assays, all four compounds bound to the mu opioid receptor with high affinity. When bovine striatal membranes were incubated with any of the four dihydrocodeinones, binding to the mu receptor was inhibited in a concentration-dependent, wash-resistant manner. Saturation binding experiments demonstrated that the wash-resistant inhibition of mu binding was due to a decrease in the Bmax value for the binding of the mu-selective peptide [3H][D-Ala2, MePhe4,Gly(ol)5] enkephalin and not a change in the Kd value, suggesting an irreversible interaction of the compounds with the mu receptor. In the mouse 55 degrees C warm water tail-flick test, both CACO and N-CPM-CACO acted as short-term mu-selective agonists when administered by i. c.v. injection, whereas CAM and MC-CAM produced no measurable antinociception at doses up to 30 nmol. Pretreatment of mice for 24 h with any of the four dihydrocodeinone derivatives produced a dose-dependent antagonism of antinociception mediated by the mu but not the delta or kappa receptors. Long-term antagonism of morphine-induced antinociception lasted for at least 48 h after i.c. v. administration. Finally, shifts in the morphine dose-response lines after 24-h pretreatment with the four dihydrocodeinone compounds suggest that the nitrocinnamoylamino derivatives may produce a greater magnitude long-term antagonism of morphine-induced antinociception than the chlorocinnamoylamino analogs. (+info)A-Current down-modulated by sigma receptor in frog pituitary melanotrope cells through a G protein-dependent pathway. (2/746)
Gramicidin perforated patch-clamp recordings were used to study the effects of two sigma 1 receptor ligands, (+)-N-cyclopropylmethyl-N-methyl-1, 4-diphenyl-1-ethyl-but-3-en-1-ylamine hydrochloride (JO 1784) and (+)-pentazocine, on the transient outward potassium current (IA) in cultured frog melanotrope cells. (+)-Pentazocine reversibly decreased the current amplitude in a dose-dependent manner. The effects of (+)-pentazocine were mimicked by JO 1784 and were markedly reduced by the sigma 1 receptor antagonist, N, N-dipropyl-2-[4-methoxy-3-2(2-phenylethoxy)phenyl]-ethylamine monohydrochloride (NE 100). Inactivation rate of IA was best fitted with a double exponential function, yielding time constants of 23.7 and 112.5 ms. (+)-Pentazocine (20 microM) accelerated the current decay, decreasing the time constants to 10.7 and 59 ms, respectively. Current-voltage experiments revealed that (+)-pentazocine (20 microM) did neither modify the open-state I/V curves nor the voltage dependence of IA. However, (+)-pentazocine (20 microM) shifted the steady-state inactivation curve toward more negative potentials and increased the time constant of the time-dependent removal of inactivation. In whole-cell experiments, internal dialysis of guanosine-5'-O-(3-thiophosphate) (100 microM) irreversibly prolonged the response to (+)-pentazocine. In addition, cholera toxin pretreatment (1 microgram. ml-1; 12 h) suppressed the inhibition of IA by (+)-pentazocine (20 microM). It is concluded that in frog melanotrope cells, a cholera toxin-sensitive, G protein-dependent inhibition of IA through a sigma 1 receptor activation, at least partially, underlies the excitatory effect of sigma ligands. (+info)Dehydrodicaffeic acid dilactone, an inhibitor of catechol-O-methyl transferase. (3/746)
In the screening of catechol-O-methyltransferase inhibitors, three compounds were isolated from the culture filtrate of a mushroom, Inonotus sp. One was 3,4-dihydroxycinnamic acid (caffeic acid) which had been reported as an inhibitor of this enzyme. The others were the dextrorotatory 2,6-bis-(3',4'-dihydroxyphenyl)-3,7-dioxabicyclo-[3,3,0]-octane 4,8-dione (dehydrodicaffeic acid dilactone) andits antipode. These new compounds inhibited both dopamine beta-hydroxylase and dopa decarboxylase and showed hypotensive activity in the SH rat. (+info)Membrane tubule-mediated reassembly and maintenance of the Golgi complex is disrupted by phospholipase A2 antagonists. (4/746)
Although membrane tubules can be found extending from, and associated with, the Golgi complex of eukaryotic cells, their physiological function has remained unclear. To gain insight into the biological significance of membrane tubules, we have developed methods for selectively preventing their formation. We show here that a broad range of phospholipase A2 (PLA2) antagonists not only arrest membrane tubule-mediated events that occur late in the assembly of the Golgi complex but also perturb its normal steady-state tubulovesicular architecture by inducing a reversible fragmentation into separate "mini-stacks." In addition, we show that these same compounds prevent the formation of membrane tubules from Golgi stacks in an in vitro reconstitution system. This in vitro assay was further used to demonstrate that the relevant PLA2 activity originates from the cytoplasm. Taken together, these results demonstrate that Golgi membrane tubules, sensitive to potent and selective PLA2 antagonists, mediate both late events in the reassembly of the Golgi complex and the dynamic maintenance of its steady-state architecture. In addition, they implicate a role for cytoplasmic PLA2 enzymes in mediating these membrane trafficking events. (+info)Recombination between two identical sequences within the same retroviral RNA molecule. (5/746)
As a consequence of being diploid viruses, members of the Retroviridae have a high recombination rate. To measure recombination between two identical sequences within the same RNA molecule per round of retroviral replication cycle, a murine leukemia virus based vector (JZ442 + 3' Hyg) has been constructed. It carries a drug resistance gene, hyg, and a 290-bp repeat sequence of the 3' hyg gene inserted into the 3' untranslated region of the green fluorescent protein gene (gfp). Under fluorescence microscopy, Hygr cells containing the recombinant proviruses were clear, while a green color was observed in the drug-resistant cells carrying the parental proviruses. The rate of recombination was determined by the ratio of the number of clear colonies to the total number of Hygr colonies (green and clear colonies). The rate of recombination was found to be 62% by this method. The intermolecular recombination rate between an infectious virus bearing two copies of the 290-bp segment and a noninfectious chimeric RNA virus containing only a single copy of this sequence was also measured. (+info)Transposition of IS117 of Streptomyces coelicolor A3(2) in Mycobacterium smegmatis. (6/746)
Derivatives of IS117, the Streptomyces coelicolor A3(2) 2.6 kb minicircle, transpose efficiently in Mycobacterium smegmatis, targeting chromosomal sites resembling translation start signals. Two IS117 derivatives, pIJ4696 and pIJ4697, containing a Streptomyces hygromycin-resistance gene in opposite orientations were introduced into M. smegmatis by electroporation and found to integrate into one of three specific sites. Integrations at sites A and B were frequent while integration at site C was observed only once. Only one site was occupied in each transformant. Sites A and B had either single or tandem integrations. PFGE analysis located these sites on different genomic Asel fragments. The sequences of the chromosome-IS117 junctions confirmed that integration was via the same IS117 attachment site as in Streptomyces, that there was no target site duplication, and that the orientation of IS117 at each site was fixed. In contrast to the situation in Streptomyces lividans, no deletions were created by the transposition and no circular forms could be detected. Comparison of the three M. smegmatis chromosomal 15117 target sites (attB) with known primary and secondary S. lividans attB sites showed that only a 2 bp 'AG' sequence at the crossover point was conserved. Dividing the attB sites into two groups produced two longer consensus target sites, GtcAAGg and gCCGATAGg. Most of the IS117 target sites resemble translational start sites, and site C resembles strongly the amino-terminal sequence of a Mycobacterium tuberculosis aminopeptidase. The level of hygromycin resistance in the transformants was high and independent of the site of integration, the number of copies integrated, or the orientation of the hyg gene. pIJ4696 at all three sites was stable in M. smegmatis in the absence of selection for at least 60 cell divisions. pIJ4696, pIJ4697 and other IS117 derivatives are promising vectors for the stable, integrative cloning of genes in M. smegmatis. (+info)kappa-Opioid receptor effects of butorphanol in rhesus monkeys. (7/746)
Butorphanol and nalbuphine have substantial affinity for mu and kappa-opioid receptor sites, yet their behavioral effects in monkeys are largely consistent with a mu receptor mechanism of action. Using ethylketocyclazocine (EKC) discrimination and diuresis assays in rhesus monkeys (Macaca mulatta), the purpose of the current investigation was to characterize the in vivo kappa-opioid activity of these compounds through the use of an insurmountable mu-opioid receptor antagonist, clocinnamox. Alone, butorphanol (0.001-0.032 mg/kg i.m.) failed to generalize to EKC, and pretreatment with the competitive opioid receptor antagonist quadazocine (0.1 or 0.32 mg/kg i.m.) did not alter this generalization. At 24 h after clocinnamox (0.1 mg/kg i.m.) administration, butorphanol fully generalized to EKC, and this generalization was maintained in two of three monkeys at 72 h. Parallel results were observed in diuresis: butorphanol alone and in the presence of quadazocine (1 mg/kg i.m.) did not alter urine output, and a marked diuretic effect was demonstrated 24 h to 2 weeks after clocinnamox administration. Clocinnamox did not alter the discriminative stimulus or diuretic effects of nalbuphine or of the kappa-opioid receptor agonists EKC or U69593. These results are consistent with an in vivo agonist activity of butorphanol at kappa-opioid receptors that can only be demonstrated when an insurmountable antagonist has substantially eliminated the dominant receptor population through which it exerts its action. (+info)Enhancer-blocking activity within the DNase I hypersensitive site 2 to 6 region between the TCR alpha and Dad1 genes. (8/746)
Although tightly linked, the TCR alpha and delta genes are expressed specifically in T lymphocytes, whereas the Dad1 gene is ubiquitously expressed. Between TCR alpha and Dad1 are eight DNase I hypersensitive sites (HS). HS1 colocalizes with the TCR alpha enhancer (Ealpha) and is T cell-specific; HS2, -3, -4, -5, and -6 map downstream of HS1 and are tissue-nonspecific. The region spanning HS2-6 was reported to display chromatin-opening activity and to confer copy number-dependent and integration site-independent transgene expression in transgenic mice. Here, we demonstrate that HS2-6 also displays enhancer-blocking activity, as it can block an enhancer from activating a promoter when located between the two in a chromatin-integrated context, and can do so without repressing either the enhancer or the promoter. Multiple enhancer-blocking elements are arrayed across HS2-6. We show that HS2-6 by itself does not activate transcription in chromatin context, but can synergize with an enhancer when located upstream of an enhancer and promoter. We propose that HS2-6 primarily functions as an insulator or boundary element that may be critical for the autonomous regulation of the TCR alpha and Dad1 genes. (+info)Cinnamic acid derivatives have antimicrobial activities in cosmetics - Wuhan LANDMARK Industrial Co., Ltd.
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Benzyl cinnamate
... can be prepared by heating benzyl chloride and excess sodium cinnamate in water to 100-115 °C or by heating ... Benzyl cinnamate is the chemical compound which is the ester derived from cinnamic acid and benzyl alcohol. Benzyl cinnamate ... "Benzyl cinnamate". Sigma-Aldrich. George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ... Benzyl cinnamate is used in heavy oriental perfumes and as a fixative. It is used as a flavoring agent. It is used ...
Methyl cinnamate
Food Chemicals Codex Eucalyptus oil Methyl cinnamate, at goodscents.com Methyl cinnamate, at Sigma-Aldrich "Methyl cinnamate". ... Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is ... Methyl cinnamate is used in the flavor and perfume industries. The flavor is fruity and strawberry-like; and the odor is sweet ... Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2-6% fresh weight yield in the leaf and ...
Methylecgonine cinnamate
... can dimerize to the truxillic acid derivative truxilline. It is notable that methylecgonine cinnamate ... Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, ... the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing ...
Ethyl cinnamate
... is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon.[citation needed] ... Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note". The p-methoxy derivative is ...
Cinnamate hydroxylase
... may refer to: Trans-cinnamate 2-monooxygenase Trans-cinnamate 4-monooxygenase This disambiguation page ...
Cinnamate beta-D-glucosyltransferase
Other names in common use include uridine diphosphoglucose-cinnamate glucosyltransferase, and UDPG:t-cinnamate ... In enzymology, a cinnamate beta-D-glucosyltransferase (EC 2.4.1.177) is an enzyme that catalyzes the chemical reaction UDP- ... The systematic name of this enzyme class is UDP-glucose:trans-cinnamate beta-D-glucosyltransferase. ... the two substrates of this enzyme are UDP-glucose and trans-cinnamate, whereas its two products are UDP and trans-cinnamoyl ...
Trans-cinnamate 4-monooxygenase
... cytochrome P450 cinnamate 4-hydroxylase, cinnamate 4-hydroxylase, cinnamate 4-monooxygenase, cinnamate hydroxylase, cinnamic 4- ... In enzymology, a trans-cinnamate 4-monooxygenase (EC 1.14.14.91) is an enzyme that catalyzes the chemical reaction trans- ... The systematic name of this enzyme class is trans-cinnamate,NADPH:oxygen oxidoreductase (4-hydroxylating). Other names in ... trans-cinnamate 4-hydroxylase, and trans-cinnamic acid 4-hydroxylase. Potts JR, Weklych R, Conn EE, Rowell J (1974). "The 4- ...
Trans-cinnamate 2-monooxygenase
... cinnamate 2-monooxygenase, cinnamic 2-hydroxylase, cinnamate 2-hydroxylase, and trans-cinnamic acid 2-hydroxylase. This enzyme ... In enzymology, a trans-cinnamate 2-monooxygenase (EC 1.14.13.14) is an enzyme that catalyzes the chemical reaction trans- ... The systematic name of this enzyme class is trans-cinnamate,NADPH:oxygen oxidoreductase (2-hydroxylating). Other names in ... H2O The 4 substrates of this enzyme are trans-cinnamate, NADPH, H+, and O2, whereas its 3 products are 2-hydroxycinnamate, ...
Rosmarinic acid
"Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden". Journal of the Science of Food and Agriculture ...
Octyl methoxycinnamate
Ngan, Vanessa (2012). "Allergy to cinnamate". DermNet NZ. Retrieved 18 October 2021.{{cite web}}: CS1 maint: url-status (link) ...
Rainer Ludwig Claisen
Synthesis of cinnamates by reacting aromatic aldehydes with esters. The reaction is known as the Claisen reaction and was ...
Phenylpropanoid
Ethyl cinnamate is a common example. Reduction of the carboxylic acid functional groups in the cinnamic acids provides the ... Hydroxylation of cinnamic acid in the 4-position by trans-cinnamate 4-monooxygenase leads to p-coumaric acid, which can be ...
Jacobsen epoxidation
"Enantioselective Catalytic Epoxidation of Cinnamate Esters". Tetrahedron. 50 (15): 4323-4334. doi:10.1016/S0040-4020(01)89369-8 ...
Deoxycholic acid
Clifford M (1999). "Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden". J. Sci. Food Agric. 79 (3 ...
Plicatin A
Rasool, Nazli; Khan, Abdul Qasim; Malik, Abdul (1990). "Plicatin a and B, two phenolic cinnamates from Psoralea plicata". ...
Chlorogenic acid
The analysis and characterization of chlorogenic acids and other cinnamates". In Santos-Buelga, C.; Williamson, G. (eds.). ... Clifford, M. N. (1999). "Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden". Journal of the ...
Plicatin B
Plicatin A and B, two phenolic cinnamates from Psoralea plicata. Nazli Rasool, Abdul Qasim Khan and Abdul Malik, Phytochemistry ...
UV filter
This is evidenced by cinnamates, salicylates, benzylidine camphor, and dibenzoylmethane derivatives. Octyl methoxycinnamate ( ... "The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxy cinnamate (EHMC) in ... Cinnamates Ethylhexyl methoxycinnamate (OMC) Isoamyl p-methoxycinnamate (IMC, amiloxate) Camphor derivatives Terephtalydene ...
1,3-Dipolar cycloaddition
For methyl cinnamate, the two substituents (Ph v.s. COOMe) compete at withdrawing electrons from the alkene. The carboxyl is ... For example, consider the cycloaddition of diazomethane to three dipolarophiles: methyl acrylate, styrene or methyl cinnamate. ...
Shea nut and butter production in Burkina Faso
"Anti-inflammatory and chemopreventive effects of triterpene cinnamates and acetates from shea fat". Journal of Oleo Science. 59 ...
Shea butter
"Anti-inflammatory and chemopreventive effects of triterpene cinnamates and acetates from shea fat". Journal of Oleo Science. 59 ...
Melaleuca viridiflora
Another population is rich in methyl cinnamate with two chemotypes. Melaleuca viridiflora is a useful and adaptable small tree ...
Asymmetric nucleophilic epoxidation
Lanthanide-mediated epoxidation has been successfully applied to cinnamates and β-heteroaryl unsaturated esters. Amides are ...
14-Cinnamoyloxycodeinone
It is a derivative of hydroxycodeinone, being the 14-cinnamate ester. In another paper, Buckett assigns the potency as 177 with ...
Cinnamon basil
It contains methyl cinnamate, giving it a flavor reminiscent of cinnamon. Cinnamon basil has somewhat narrow, slightly serrated ...
4-Vinylphenol
The enzyme cinnamate decarboxylase converts p-coumaric acid to 4-vinylphenol. 4-Vinylphenol is further reduced to 4-ethylphenol ...
4-Ethylphenol
Decarboxylation gives 4-vinylphenol as catalyzed by the enzyme cinnamate decarboxylase. 4-Vinylphenol is further reduced to 4- ...
Ocotea quixos
The same study of methyl cinnamate did not show this effect. It has also been shown that this oil can reduce the chance of ... The taste of Ecuadorian cinnamon is thought to come from the presence of methyl cinnamate and trans-cinnamaldehyde which are ...
Mandelic acid
Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Phenylpyruvic acid is another ...
4-Hydroxycinnamate decarboxylase
The yeast converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase. 4-Hydroxycinnamate decarboxylase can also be ...
n-Butyl cinnamate
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Cinnamyl cinnamate|Cas No.:122-69-0--Yingcheng Wuhan Organic Material Co., Ltd.
Ethyl cinnamate analytical standard 103-36-6
Ethyl cinnamate analytical standard; CAS Number: 103-36-6; EC Number: 203-104-6; Synonyms: 3-Phenyl-2-propenoic acid ethyl ... Ethyl cinnamate may be used as a reference standard:. *to determine the toxic effects of ethyl cinnamate, affecting the growth ... in the determination of ethyl cinnamate in samples of red wine using gas chromatography coupled with ion-trap mass ...
Cinnamyl Cinnamate - Vigon
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Drug-Induced Photosensitivity: Background, Pathophysiology, Etiology
Drug-induced photosensitivity refers to the development of cutaneous disease as a result of the combined effects of a chemical and light. Exposure to either the chemical or the light alone is not sufficient to induce the disease; however, when photoactivation of the chemical occurs, one or more cutaneous manifestations may arise.
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Synthesis and Study of a New Ester Homologous Series: Ethyl-p-(p/-n-alkoxy Cinnamoyloxy)Cinnamates | Abstract
... cinnamates is synthesized and studied for liquid crystal behavior and its corre.. ... Synthesis and Study of a New Ester Homologous Series: Ethyl-p-(p/-n-alkoxy Cinnamoyloxy)Cinnamates. Author(s): Patel R.B.a and ... An ester homologous series entitled Ethyl-p-[p/-n-alkoxy cinnamoyloxy] cinnamates is synthesized and studied for liquid crystal ...
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Drug-Induced Photosensitivity Differential Diagnoses
Drug-induced photosensitivity refers to the development of cutaneous disease as a result of the combined effects of a chemical and light. Exposure to either the chemical or the light alone is not sufficient to induce the disease; however, when photoactivation of the chemical occurs, one or more cutaneous manifestations may arise.
Phenyl Ethyl Cinnamate . Berjé Inc : Phenyl Ethyl Cinnamate Supplier
Sign up to our inquiry list to receive additional information about Phenyl Ethyl Cinnamate. ... Phenyl Ethyl Cinnamate. Phenyl Ethyl Cinnamate Supplier, Phenyl Ethyl Cinnamate Distributor, Phenyl Ethyl Cinnamate ... Phenyl Ethyl Cinnamate. Name:. Phone:. Email:. Company:. Company Website:. Company Address:. City:. State:. Postal Code:. ... Assay of Phenyl Ethyl Cinnamate. 90-100%. All scientific, regulatory and technical data is a guide for product identification ...
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Cinnamyl cinnamate CAS:122-69-0 - Jinan Boss Chemical Industry Co.,Ltd
Cinnamyl cinnamate is one of the most important constituents of storax: Liqidambar orientale, Liquidambar styracifluum L. ... Synonyms: STYRACINE;3-Phenyl-2-propen-1-yl 3-phenyl propenoate;3-PHENYLALLYL CINNAMATE;3-PHENYL-2-PROPENYL CINNAMATE;(E)-3- ... Cinnamyl cinnamate CAS:122-69-0. FAQ:. 1.What is about your company strength?. Since 2005, we have more than 15 years ... PHENYL-ACRYLIC ACID (E)-3-PHENYL-ALLYL ESTER;CINNAMYL CINNAMATE;CINNAMIC ACID CINNAMYL ESTER;FEMA 2298 ...
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KEGG PATHWAY: Degradation of aromatic compounds - Reference pathway
Microorganisms are known to be capable of degrading diverse chemical substances including man-made chemicals in the environment that are mostly aromatic compounds. This diagram illustrates combination patterns of reaction modules for biodegradation of aromatic compounds, consisting of three main types of ring dihydroxylation modules, followed by meta- or ortho-cleavage modules, together with an optional preprocessing module for converting methyl group to carboxyl group on the aromatic ring ...