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Chemical Compound Review

Marlican     1-phenyldodecane

Synonyms: Alkane, Alkylbenzene, Laurylbenzene, Phenyldodecan, DODECYLBENZENE, ...
 
 
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Disease relevance of dodecylbenzene

  • A combination of 22 breath VOCs, predominantly alkanes, alkane derivatives, and benzene derivatives, discriminated between patients with and without lung cancer, regardless of stage (all p<0.0003) [1].
  • The gene encoding the alkane omega-hydroxylase (AlkB; EC 1.14.15.3) from Pseudomonas oleovorans was expressed in Escherichia coli [2].
  • Molecular wires comprising a Ru(II)- or Re(I)-complex head group, an aromatic tail group, and an alkane linker reversibly inhibit the activity of the copper amine oxidase from Arthrobacter globiformis (AGAO), with K(i) values between 6 muM and 37 nM [3].
  • Controlled and functional expression of the Pseudomonas oleovorans alkane utilizing system in Pseudomonas putida and Escherichia coli [4].
  • The number of enzymes thought to have nonheme diiron sites has been expanded to include alkene monooxygenase from Xanthobacter strain Py2 and the membrane bound alkane hydroxylase from Pseudomonas oleovorans (AlkB) [5].
 

High impact information on dodecylbenzene

  • Here, we show that this T cell antigen is a member of a family of branched, alkane lipids that vary in length (C30-34) and are produced by medically important mycobacteria such as M. tuberculosis and M. bovis Bacille-Calmette-Guerin [6].
  • This catalyst for alkane hydroxylation at room temperature opens new opportunities for clean, selective hydrocarbon activation for chemical synthesis and bioremediation [7].
  • Genome and proteome of long-chain alkane degrading Geobacillus thermodenitrificans NG80-2 isolated from a deep-subsurface oil reservoir [8].
  • In spring 2002, maximum mixing ratios of ethane [34 parts per 109 by volume (ppbv)], propane (20 ppbv), and n-butane (13 ppbv) were observed in north-central Texas. The elevated alkane mixing ratios are attributed to emissions from the oil and natural gas industry [9].
  • These gene disruptions revealed the diploid nature of this alkane- and fatty acid-utilizing yeast by showing that it contains two copies of each gene [10].
 

Chemical compound and disease context of dodecylbenzene

  • Application of the alkane n-dodecane to the dorsal skin of 6-8 week old female SENCAR mice initiated with 10 nmol dimethylbenz[a]anthracene led to papilloma formation in the majority of treated animals [11].
  • Biodegradation of petroleum hydrocarbons by psychrotrophic Pseudomonas strains possessing both alkane (alk) and naphthalene (nah) catabolic pathways [12].
  • Partition of alkane by an extracellular vesicle derived from hexadecane-grown Acinetobacter [13].
  • Physiological and regulatory mechanisms that allow the alkane-oxidizing bacterium Pseudomonas butanovora to consume C2 to C8 alkane substrates via butane monooxygenase (BMO) were examined [14].
  • Alkane-grown cells of Mycobacterium vaccae JOB5 cometabolically degrade the gasoline oxygenate methyl tertiary butyl ether (MTBE) through the activities of an alkane-inducible monooxygenase and other enzymes in the alkane oxidation pathway [15].
 

Biological context of dodecylbenzene

  • The OCT plasmid encodes enzymes for alkane hydroxylation and alkanol dehydrogenation [4].
  • We found the induction kinetics of alkane hydroxylase to be similar in both species [4].
  • Thus, the expression of the alkBAC operon is regulated by a 99-kDa protein, whereas the 48-kDa protein is probably a component of the alkane hydroxylase complex [16].
  • We have determined the nucleotide sequence of the 2.5-kilobase pair alkA region and analyzed the role of its translation products in alkane oxidation [17].
  • Other than the dealkylation of C-24 alkane or alkene substituents, side-chain cleavage of sterols is uncommon to insects [18].
 

Anatomical context of dodecylbenzene

  • Translocation and activation of protein kinase C by the plasma cell tumor-promoting alkane pristane [19].
  • Accordingly, the action of the halogenated alkane anesthetic halothane on voltage-dependent Ca currents in neonatal rat sensory neurons was examined using whole-cell patch-clamp recordings [20].
  • The amino-terminal sequence of the purified cytoplasmic membrane alkane hydroxylase was determined and was found to be in agreement with the nucleotide sequence [21].
  • With isolated microsomes conversion of fatty acid to alkane required CoA, ATP, and NADH whereas conversion of an aldehyde to alkane did not require the addition of cofactors [22].
  • Our search to find a convenient animal tissue to study alkane biosynthesis resulted in the finding that the uropygial gland (a modified sebaceous gland) of the eared grebe (Podiceps nigricollis) produces large amounts of alkanes [22].
 

Associations of dodecylbenzene with other chemical compounds

  • Activation of the sulfhydryl group by Mo centers: kinetics of reaction of benzyl radical with a binuclear Mo(micro-SH)Mo complex and with arene and alkane thiols [23].
  • Using nanometer thick tunneling barriers with specifically attached cytochrome c, the electron-transfer rate constant was studied as a function of the SAM composition (alkane versus terthiophene), the omega-terminating group type (pyridine, imidazole, nitrile), and the solution viscosity [24].
  • Theoretical study of the mechanism of alkane hydroxylation and ethylene epoxidation reactions catalyzed by diiron bis-oxo complexes. The effect of substrate molecules [25].
  • Dynamic aspects of alkane hydroxylation mediated by Compound I of cytochrome P450 are discussed from classical trajectory calculations at the B3LYP level of density functional theory [26].
  • A modeling approach that allowed for partial conformational relaxation of hEAG model structures upon ligand docking suggests that high-affinity block of ether à go-go channels is mediated by an anchoring of the clofilium alkane tail between S6 and the pore helices [27].
  • The oxidation of norcarane by several recently isolated strains (Hydrocarboniphaga effusa AP103, rJ4, and rJ5, whose alkane-oxidizing enzymes have not yet been identified) is also reported [28].
 

Gene context of dodecylbenzene

 

Analytical, diagnostic and therapeutic context of dodecylbenzene

  • We have measured the contact angle of microsized and nanosized alkane droplets partially wetting a model substrate using true noncontact atomic force microscopy [33].
  • The cooling of confined liquid below the freezing temperature leads to crystallization with alkane molecules lying on the substrate with the symmetry axis parallel to the surface normal [34].
  • In an attempt to elucidate the molecular basis for concentration (isotherm) effects on retention in gas-liquid chromatography, configurational-bias Monte Carlo simulations in the Gibbs ensemble were carried out to investigate changes in analyte partitioning caused by overloading a model chromatographic system with either an alkane or an alcohol [35].
  • The self-assembled monolayers (SAMs) of normal alkanes (n-C(n)H(2n+2)) with different carbon chain lengths (n=14-38) in the interfaces between alkane solutions (or liquids), and the reconstructed Au (111) surfaces have been systematically studied by means of scanning tunneling microscopy (STM) [36].
  • The alkane likewise did not increase the number of pyknotic basal keratinocytes indicating that toxicity would not account for the low Stage I activity of this agent in the way proposed for mezerein which was the most active in this respect, inducing a significant increase 48 h after treatment [37].

References

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  2. Mössbauer studies of alkane omega-hydroxylase: evidence for a diiron cluster in an integral-membrane enzyme. Shanklin, J., Achim, C., Schmidt, H., Fox, B.G., Münck, E. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Reversible inhibition of copper amine oxidase activity by channel-blocking ruthenium(II) and rhenium(I) molecular wires. Contakes, S.M., Juda, G.A., Langley, D.B., Halpern-Manners, N.W., Duff, A.P., Dunn, A.R., Gray, H.B., Dooley, D.M., Guss, J.M., Freeman, H.C. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  4. Controlled and functional expression of the Pseudomonas oleovorans alkane utilizing system in Pseudomonas putida and Escherichia coli. Eggink, G., Lageveen, R.G., Altenburg, B., Witholt, B. J. Biol. Chem. (1987) [Pubmed]
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  8. Genome and proteome of long-chain alkane degrading Geobacillus thermodenitrificans NG80-2 isolated from a deep-subsurface oil reservoir. Feng, L., Wang, W., Cheng, J., Ren, Y., Zhao, G., Gao, C., Tang, Y., Liu, X., Han, W., Peng, X., Liu, R., Wang, L. Proc. Natl. Acad. Sci. U.S.A. (2007) [Pubmed]
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  12. Biodegradation of petroleum hydrocarbons by psychrotrophic Pseudomonas strains possessing both alkane (alk) and naphthalene (nah) catabolic pathways. Whyte, L.G., Bourbonniére, L., Greer, C.W. Appl. Environ. Microbiol. (1997) [Pubmed]
  13. Partition of alkane by an extracellular vesicle derived from hexadecane-grown Acinetobacter. Käppeli, O., Finnerty, W.R. J. Bacteriol. (1979) [Pubmed]
  14. Product repression of alkane monooxygenase expression in Pseudomonas butanovora. Doughty, D.M., Sayavedra-Soto, L.A., Arp, D.J., Bottomley, P.J. J. Bacteriol. (2006) [Pubmed]
  15. Induction of methyl tertiary butyl ether (MTBE)-oxidizing activity in Mycobacterium vaccae JOB5 by MTBE. Johnson, E.L., Smith, C.A., O'Reilly, K.T., Hyman, M.R. Appl. Environ. Microbiol. (2004) [Pubmed]
  16. Alkane utilization in Pseudomonas oleovorans. Structure and function of the regulatory locus alkR. Eggink, G., Engel, H., Meijer, W.G., Otten, J., Kingma, J., Witholt, B. J. Biol. Chem. (1988) [Pubmed]
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  18. Biosynthesis of a C21 steroid conjugate in an insect. The conversion of [14C]cholesterol to 5-[14C]pregnen-3 beta,20 beta-diol glucoside in the tobacco hornworm, Manduca sexta. Thompson, M.J., Svoboda, J.A., Lusby, W.R., Rees, H.H., Oliver, J.E., Weirich, G.F., Wilzer, K.R. J. Biol. Chem. (1985) [Pubmed]
  19. Translocation and activation of protein kinase C by the plasma cell tumor-promoting alkane pristane. Janz, S., Gawrisch, K., Lester, D.S. Cancer Res. (1995) [Pubmed]
  20. Halothane blocks low-voltage-activated calcium current in rat sensory neurons. Takenoshita, M., Steinbach, J.H. J. Neurosci. (1991) [Pubmed]
  21. The Pseudomonas oleovorans alkane hydroxylase gene. Sequence and expression. Kok, M., Oldenhuis, R., van der Linden, M.P., Raatjes, P., Kingma, J., van Lelyveld, P.H., Witholt, B. J. Biol. Chem. (1989) [Pubmed]
  22. Microsomal preparation from an animal tissue catalyzes release of carbon monoxide from a fatty aldehyde to generate an alkane. Cheesbrough, T.M., Kolattukudy, P.E. J. Biol. Chem. (1988) [Pubmed]
  23. Activation of the sulfhydryl group by Mo centers: kinetics of reaction of benzyl radical with a binuclear Mo(micro-SH)Mo complex and with arene and alkane thiols. Franz, J.A., Birnbaum, J.C., Kolwaite, D.S., Linehan, J.C., Camaioni, D.M., Dupuis, M. J. Am. Chem. Soc. (2004) [Pubmed]
  24. Charge-transfer mechanism for cytochrome c adsorbed on nanometer thick films. Distinguishing frictional control from conformational gating. Khoshtariya, D.E., Wei, J., Liu, H., Yue, H., Waldeck, D.H. J. Am. Chem. Soc. (2003) [Pubmed]
  25. Theoretical study of the mechanism of alkane hydroxylation and ethylene epoxidation reactions catalyzed by diiron bis-oxo complexes. The effect of substrate molecules. Musaev, D.G., Basch, H., Morokuma, K. J. Am. Chem. Soc. (2002) [Pubmed]
  26. A theoretical study of the dynamic behavior of alkane hydroxylation by a compound I model of cytochrome P450. Yoshizawa, K., Kamachi, T., Shiota, Y. J. Am. Chem. Soc. (2001) [Pubmed]
  27. Molecular determinants for high-affinity block of human EAG potassium channels by antiarrhythmic agents. Gessner, G., Zacharias, M., Bechstedt, S., Schönherr, R., Heinemann, S.H. Mol. Pharmacol. (2004) [Pubmed]
  28. Profiling mechanisms of alkane hydroxylase activity in vivo using the diagnostic substrate norcarane. Rozhkova-Novosad, E.A., Chae, J.C., Zylstra, G.J., Bertrand, E.M., Alexander-Ozinskas, M., Deng, D., Moe, L.A., van Beilen, J.B., Danahy, M., Groves, J.T., Austin, R.N. Chem. Biol. (2007) [Pubmed]
  29. The genes rubA and rubB for alkane degradation in Acinetobacter sp. strain ADP1 are in an operon with estB, encoding an esterase, and oxyR. Geissdörfer, W., Kok, R.G., Ratajczak, A., Hellingwerf, K.J., Hillen, W. J. Bacteriol. (1999) [Pubmed]
  30. Alkane hydroxylase from Acinetobacter sp. strain ADP1 is encoded by alkM and belongs to a new family of bacterial integral-membrane hydrocarbon hydroxylases. Ratajczak, A., Geissdörfer, W., Hillen, W. Appl. Environ. Microbiol. (1998) [Pubmed]
  31. Cloning and characterization of the peroxisomal acyl CoA oxidase ACO3 gene from the alkane-utilizing yeast Yarrowia lipolytica. Wang, H., Le Clainche, A., Le Dall, M.T., Wache, Y., Pagot, Y., Belin, J.M., Gaillardin, C., Nicaud, J.M. Yeast (1998) [Pubmed]
  32. The pentafunctional FAS1 genes of Saccharomyces cerevisiae and Yarrowia lipolytica are co-linear and considerably longer than previously estimated. Köttig, H., Rottner, G., Beck, K.F., Schweizer, M., Schweizer, E. Mol. Gen. Genet. (1991) [Pubmed]
  33. Nonlinear dependence of the contact angle of nanodroplets on contact line curvature. Checco, A., Guenoun, P., Daillant, J. Phys. Rev. Lett. (2003) [Pubmed]
  34. Confinement-induced ordering of alkanes between an elastomer and a solid surface. Nanjundiah, K., Dhinojwala, A. Phys. Rev. Lett. (2005) [Pubmed]
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