phthalic anhydrides


Summary: Phthalic acid anhydrides. Can be substituted on any carbon atom. Used extensively in industry and as a reagent in the acylation of amino- and hydroxyl groups.

Top Publications

  1. O Brien A, Smith A, Ó Fágáin C. Effects of phthalic anhydride modification on horseradish peroxidase stability and activity. Biotechnol Bioeng. 2003;81:233-40 pubmed
    ..The kinetics of both HRPs with the substrates ABTS, ferrocyanide, ferulic acid, and indole-3-propionic acid were measured, as was binding of the inhibitor benzhydroxamic acid. Small improvements in the catalytic properties were detected...
  2. Liu P, Sheu J, Lin P, Lin C, Liu Y, Ho L, et al. Expression of Nur77 induced by an n-butylidenephthalide derivative promotes apoptosis and inhibits cell growth in oral squamous cell carcinoma. Invest New Drugs. 2012;30:79-89 pubmed publisher
    ..These results indicate that PCH4 may serve as a potential anti-tumor drug for OSCC therapy...
  3. Ko W, Liao C, Shih C, Lei C, Chen C. Relaxant effects of butylidenephthalide in isolated dog blood vessels. Planta Med. 2002;68:1004-9 pubmed
    ..Phe:phenylephrine PGF 2alpha :prostaglandin F 2alpha CA:coronary artery FV:femoral vein FA:femoral artery MA:mesenteric artery cAMP:adenosine 3',5'-cyclic monophosphate cGMP:guanosine 3',5'-cyclic monophosphate PDE:phosphodiesterase..
  4. Lin P, Chen Y, Chiu S, Yu Y, Chen S, Chien M, et al. Orphan nuclear receptor, Nurr-77 was a possible target gene of butylidenephthalide chemotherapy on glioblastoma multiform brain tumor. J Neurochem. 2008;106:1017-26 pubmed publisher
    ..In summary, our results suggest that up-regulation of Nur77 may explain the antitumoral activity of BP in brain tumor cells...
  5. Chen Y, Jian M, Lin C, Kang J, Chen S, Lin P, et al. The induction of orphan nuclear receptor Nur77 expression by n-butylenephthalide as pharmaceuticals on hepatocellular carcinoma cell therapy. Mol Pharmacol. 2008;74:1046-58 pubmed publisher
    ..N-Butylidenephthalide induced apoptosis in hepatocellular carcinoma cells, both in vitro and in vivo, suggesting a potential clinical use of this compound for improving the prognosis of hepatocellular carcinoma cells...
  6. Ko W, Sheu J, Tzeng S, Chen C. The selective antianginal effect without changing blood pressure of butylidenephthalide in conscious rats. Planta Med. 1998;64:229-32 pubmed
    ..Therefore, Bdph, found in the rhizome of Ligusticum chuaxiong Hort. (L. wallichii Franch., Umbelliferae), appears to have selective antianginal effect without changing blood pressure and heart rate...
  7. Tsai N, Chen Y, Lee C, Lin P, Cheng Y, Chang W, et al. The natural compound n-butylidenephthalide derived from Angelica sinensis inhibits malignant brain tumor growth in vitro and in vivo. J Neurochem. 2006;99:1251-62 pubmed
    ..These in vitro and in vivo anti-cancer effects indicate that BP could serve as a new anti-brain tumor drug...
  8. Wei C, Lin C, Yu Y, Lin C, Lin P, Wu M, et al. n-Butylidenephthalide induced apoptosis in the A549 human lung adenocarcinoma cell line by coupled down-regulation of AP-2alpha and telomerase activity. Acta Pharmacol Sin. 2009;30:1297-306 pubmed publisher
    ..To investigate the role of hTERT gene expression and AP-2alpha in n-butylidenephthalide (n-BP)-induced apoptosis in A549 lung cancer cells...
  9. Ayyadurai S, Worrall A, Bernstein J, Angelopoulos A. Perfluorosulfonic acid membrane catalysts for optical sensing of anhydrides in the gas phase. Anal Chem. 2010;82:6265-72 pubmed publisher

More Information

Publications104 found, 100 shown here

  1. Rosqvist S, Johannesson G, Lindh C, Jonsson B. Total plasma protein adducts of allergenic hexahydrophthalic and methylhexahydrophthalic anhydrides as biomarkers of long-term exposure. Scand J Work Environ Health. 2001;27:133-9 pubmed
    ..81, respectively, for HHPA and MHHPA). The in vivo decay of TPPA gave an elimination half-time of 22 days for HHPA and 24 days for MHHPA. TPPA levels of HHPA and MHHPA are excellent biomarkers of long-term exposure to anhydrides. ..
  2. Gach J, Stone N, Finch T. A series of four cases of allergic contact dermatitis to phthalic anhydride/trimellitic anhydride/glycols copolymer in nail varnish. Contact Dermatitis. 2005;53:63-4 pubmed
  3. Kawakami H, Okuyama Y, Matsumoto N, Nagaoka S. Plasma protein adsorption to nanofabricated fluorinated polyimide surface. J Biomater Sci Polym Ed. 2005;16:1023-34 pubmed
    ..We proposed that the nano-ordered hydrophilic and hydrophobic patternings formed on the top and bottom surfaces on the rubbed fluorinated polyimide film might have a significant influence on the plasma protein adsorption. ..
  4. Anthoni M, Fyhrquist N, Lehtimäki S, Alenius H, Wolff H, Lauerma A. Smad3 regulates dermal cytokine and chemokine expression and specific antibody production in murine responses to a respiratory chemical sensitizer. Int Arch Allergy Immunol. 2010;151:155-67 pubmed publisher
    ..The Smad3 molecule contributes significantly to the regulation of the cytokine and chemokine network during the CHS response to TMA. The lack of Smad3 resulted in a potent Th2 shift, confirmed by strongly impaired IgG2a levels. ..
  5. Liu M, Ma X, Xu Y, Peng L, Han M, Gao J. Liquid chromatography-tandem mass spectrometry evaluation of the pharmacokinetics of a diacid metabolite of norcantharidin loaded in folic acid-targeted liposomes in mice. J Pharm Biomed Anal. 2016;119:76-83 pubmed publisher
    ..In addition, the plausibility of formulating a safe DM-NCTD-loaded system without increasing toxicity against normal tissues needs to be determined. ..
  6. Sa R, Wang Y, Zhu S, Pan X, Yang Y, Sun Y. [Study on the dynamic variations of Z-ligustilide and n-butylidenephthalide content in essential oil of radix angelicae sinensis from different growth period]. Zhong Yao Cai. 2012;35:1738-42 pubmed
    ..Their contents showed larger difference during different growth period. The contents of Z-ligustilide and n-Butylidenephthalide of Radix Angelicae Sinensis is closely related to their growth period. ..
  7. Meyer A, Ryan J. 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives. Molecules. 2016;21: pubmed publisher
    ..examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances...
  8. Ridley W, Warren J, Nair R. Effect of tetrachlorophthalic anhydride on hepatic microsomal metabolism in rats and mice. J Toxicol Environ Health. 1988;24:217-27 pubmed
    ..These results suggest that following oral dosage TCPA is a weak inducer of microsomal enzymes in the rat. A similar effect was not observed in the mouse for the parameters tested. ..
  9. Stevens A, Bull J, Chibale K. Studies in iridoid synthesis. Chemoselective transformations of cis-1,2,4,6-tetrahydrophthalic anhydride. Org Biomol Chem. 2008;6:586-95 pubmed publisher
  10. Chiu S, Chiu T, Huang S, Chang S, Chen S, Pang C, et al. Potential therapeutic effects of N-butylidenephthalide from Radix Angelica Sinensis (Danggui) in human bladder cancer cells. BMC Complement Altern Med. 2017;17:523 pubmed publisher
    ..The incidence of bladder cancer decreased in patients who were exposed to Angelica sinensis, suggesting that BP could serve as a potential adjuvant in bladder cancer therapy regimen. ..
  11. Regal J, Mohrman M, Sailstad D. Trimellitic anhydride-induced eosinophilia in a mouse model of occupational asthma. Toxicol Appl Pharmacol. 2001;175:234-42 pubmed
    ..These studies are the first to demonstrate TMA-induced eosinophilia in mouse lung and to provide a model for comparing mechanisms and mediators responsible for the substantial eosinophilia induced by TMA and OA. ..
  12. Dearman R, Humphreys N, Skinner R, Kimber I. Allergen-induced cytokine phenotypes in mice: role of CD4 and CD8 T cell populations. Clin Exp Allergy. 2005;35:498-505 pubmed
  13. Nassif A, Le Coz C, Collet E. A rare nail polish allergen: phthalic anhydride, trimellitic anhydride and glycols copolymer. Contact Dermatitis. 2007;56:172-3 pubmed
  14. Yu Y, Zhang H, Wang W, Wang S. Selective adsorbent for the removal of immunoglobulin E in bronchial asthma. Artif Cells Blood Substit Immobil Biotechnol. 2008;36:63-73 pubmed publisher
    ..73% (1309.403IU/g agar-gel), which was higher than that without spacers (53%). The selectivity and hemocompatibility of the adsorbent were also examined, which showed good selectivity for IgE and satisfactory blood compatibility. ..
  15. Chadlia A, Farouk M. Chemical modification of Posidonia with cyclic anhydrides: effect on thermal stability. Carbohydr Res. 2010;345:264-9 pubmed publisher
    ..Thermogravimetric investigation of chemically modified Posidonia indicated a better thermal stability in comparison with the untreated Posidonia. ..
  16. Larsen C, Regal R, Regal J. Trimellitic anhydride-induced allergic response in the guinea pig lung involves antibody-dependent and -independent complement system activation. J Pharmacol Exp Ther. 2001;296:284-92 pubmed
    ..These data indicate that complement activation in the absence of antibody is not sufficient for the complete allergic response to occur. Both sensitization and the complement system are required for TMA-induced eosinophilia. ..
  17. Valstar D, Schijf M, Nijkamp F, Storm G, Arts J, Kuper C, et al. Alveolar macrophages have a dual role in a rat model for trimellitic anhydride-induced occupational asthma. Toxicol Appl Pharmacol. 2006;211:20-9 pubmed
    ..AMs seem to have a dual role in this model for TMA-induced occupational asthma since they potentiate the immediate TMA-induced decrease in lung function but tended to dampen the TMA-induced inflammatory reaction 24 h later. ..
  18. Lu L, Yang X, Li Y, Jiang S. Chemically modified bovine beta-lactoglobulin inhibits human papillomavirus infection. Microbes Infect. 2013;15:506-10 pubmed publisher
    ..These results suggest that JB01 has good potential to be developed as an effective, safe and inexpensive antiviral agent for treatment and prevention of HPV infection. ..
  19. Lindh C, Jonsson B, Johannesson G, Zhang X, Welinder H, Brittebo E. Binding of the potent allergen hexahydrophthalic anhydride in the mucosa of the upper respiratory and alimentary tract following single inhalation exposures in guinea pigs and rats. Toxicology. 1999;134:153-68 pubmed
    ..The non-extractable binding of [3H2]HHPA in the upper respiratory airways and conjunctiva may be of relevance for symptoms in workers with allergy, since they mainly develop symptoms and signs from the nose and eyes. ..
  20. Jeppsson M, Lindh C, Kristiansson M, Nielsen J, Jonsson B. Methylhexahydrophthalic anhydride adducted albumin tryptic peptides in nasal lavage fluid. Inhal Toxicol. 2009;21:1013-20 pubmed publisher
    ..The results also show a correlation between adducted peptides and albumin in nasal lavage. Furthermore, there may be a difference in the potential to induce hyperresponsiveness between adducts bound to different amino acids. ..
  21. Rahman F, Langford K, Scrimshaw M, Lester J. Polybrominated diphenyl ether (PBDE) flame retardants. Sci Total Environ. 2001;275:1-17 pubmed
    ..The manufacture of reactive and additive flame retardants is briefly discussed and their fate and behaviour in the environment is assessed. PBDE toxicology is reviewed and methods of analysis are evaluated. ..
  22. Nagaoka S, Ashiba K, Kawakami H. Biomedical properties of nanofabricated fluorinated polyimide surface. Artif Organs. 2002;26:670-5 pubmed
  23. Farraj A, Harkema J, Kaminski N. Allergic rhinitis induced by intranasal sensitization and challenge with trimellitic anhydride but not with dinitrochlorobenzene or oxazolone in A/J mice. Toxicol Sci. 2004;79:315-25 pubmed
    ..In contrast, DNCB and OXA failed to elicit the pathologic changes in the nasal airways and cytokine changes in the lung. This model may be useful for identifying other chemical respiratory allergens. ..
  24. Vanoirbeek J, Tarkowski M, Vanhooren H, De Vooght V, Nemery B, Hoet P. Validation of a mouse model of chemical-induced asthma using trimellitic anhydride, a respiratory sensitizer, and dinitrochlorobenzene, a dermal sensitizer. J Allergy Clin Immunol. 2006;117:1090-7 pubmed
    ..Both compounds induce a mixed T(H)1-T(H)2 response, but only TMA induced ventilatory changes. In the workplace avoiding skin contact with chemical sensitizers might be advised to prevent chemical-induced asthma. ..
  25. Ikai A, Kikuchi M, Nishigai M. Internal structure of ovomacroglobulin studied by electron microscopy. J Biol Chem. 1990;265:8280-4 pubmed
    ..The results may also be adapted to the internal structure of human alpha 2-macroglobulin because it was sometimes possible to observe similar ring-like internal structure in the human protein. ..
  26. Chiu S, Chen S, Huang S, Wang M, Lin S, Harn H, et al. Induction of apoptosis coupled to endoplasmic reticulum stress in human prostate cancer cells by n-butylidenephthalide. PLoS ONE. 2012;7:e33742 pubmed publisher
    ..Our results suggest that BP can cause G0/G1 phase arrest in prostate cancer cells and its cytotoxicity is mediated by ER stress induction. Thus, BP may serve as an anticancer agent by inducing ER stress in prostate cancer. ..
  27. Pawlowska M, Zukowski J, Armstrong D. Sensitive enantiomeric separation of aliphatic and aromatic amines using aromatic anhydrides as nonchiral derivatizing agents. J Chromatogr A. 1994;666:485-91 pubmed
    ..The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases...
  28. Holliday M, Dearman R, Kimber I, Coleman J. Sensitization of mice to chemical allergens modulates the responsiveness of isolated mast cells to IgE-dependent activation. Immunology. 1993;78:508-10 pubmed
    ..These results show that the function of mast cells is susceptible in vivo to regulatory influences that result from induction of an immune response. ..
  29. Li L, He L, Tan S, Guo X, Lu H, Qi Z, et al. 3-hydroxyphthalic anhydride-modified chicken ovalbumin exhibits potent and broad anti-HIV-1 activity: a potential microbicide for preventing sexual transmission of HIV-1. Antimicrob Agents Chemother. 2010;54:1700-11 pubmed publisher
    ..Because of the widespread availability and established safety profile of OVA, HP-OVA has good potential to be developed as an effective, safe, and affordable microbicide for prevention of HIV sexual transmission...
  30. Estarellas C, Quiñonero D, Frontera A, Ballester P, Morey J, Costa A, et al. MP2 study of the dual sigma/pi-anion-binding affinity of fluorinated phthallic acid anhydrides. J Phys Chem A. 2008;112:1622-6 pubmed publisher
    ..The dual sigma/pi-binding affinity of title compounds have been studied by means of ab initio and molecular interaction potential with polarization (MIPp) calculations and Bader's theory of "atoms-in-molecules". ..
  31. Turi C, Murch S. Targeted and untargeted phytochemistry of Ligusticum canbyi: indoleamines, phthalides, antioxidant potential, and use of metabolomics as a hypothesis-generating technique for compound discovery. Planta Med. 2013;79:1370-9 pubmed publisher
    ..These data provide new understandings of the phytomedicinal composition and potential mechanisms of activity of L. canbyi extracts and tissues. ..
  32. Venables K, Topping M, Howe W, Luczynska C, Hawkins R, Taylor A. Interaction of smoking and atopy in producing specific IgE antibody against a hapten protein conjugate. Br Med J (Clin Res Ed). 1985;290:201-4 pubmed
    ..7% in non-atopic smokers, 8.3% in atopic non-smokers, and nil in non-atopic non-smokers (p less than 0.025). Smoking may predispose to, and interact with atopy in, the production of specific IgE antibody to this hapten protein conjugate. ..
  33. Andrés G, Granados A, de Rossi R. Kinetic study of the hydrolysis of phthalic anhydride and aryl hydrogen phthalates. J Org Chem. 2001;66:7653-7 pubmed
    ..06, 3.02, 2.95, and 2.93 for X = H, p-Me, m-Cl, and p-Cl, respectively. The data also show that the catalysis by the neighboring carboxy group takes place only when it is ionized (i.e., as carboxylate). ..
  34. Kanno M, Kawakami H, Nagaoka S, Kubota S. Biocompatibility of fluorinated polyimide. J Biomed Mater Res. 2002;60:53-60 pubmed
  35. Serafini Fracassini D, Del Duca S, Monti F, Poli F, Sacchetti G, Bregoli A, et al. Transglutaminase activity during senescence and programmed cell death in the corolla of tobacco (Nicotiana tabacum) flowers. Cell Death Differ. 2002;9:309-21 pubmed
    ..Bis-PU was the most abundant PA-derivative before DNA laddering stage; thereafter, bis-PU generally decreased and mono-PU became the most abundant derivative. ..
  36. Thiyagarajan S, Genuino H, Åšliwa M, van der Waal J, de Jong E, van Haveren J, et al. Substituted Phthalic Anhydrides from Biobased Furanics: A New Approach to Renewable Aromatics. ChemSusChem. 2015;8:3052-6 pubmed publisher
    ..The mechanism of the final aromatization reaction step unexpectedly involves a lactone as primary intermediate. ..
  37. Griffin P, Allan L, Beckett P, Elms J, Curran A. The development of an antibody to trimellitic anhydride. Clin Exp Allergy. 2001;31:453-7 pubmed
    ..These results suggest that the current paradigm for the detection of IgE to small molecular weight reactive chemicals, which presupposes that the chemical binds to serum albumin, may need further investigation. ..
  38. Pakarinen M, Koivuluhta M, Kalkkinen N, Keskinen H, Nordman H, Estlander T, et al. Phthalic anhydride allergy: development and characterization of optimized hapten-carrier conjugates for improved diagnosis. Allergy. 2002;57:894-9 pubmed
    ..These results indicate that optimized and molecularly characterized PA-HSA conjugates can be used both in vitro and in vivo assays to improve the diagnosis of PA allergy. ..
  39. Sim Y, Shin S. Combinatorial anti-Trichophyton effects of Ligusticum chuanxiong essential oil components with antibiotics. Arch Pharm Res. 2008;31:497-502 pubmed publisher
    ..mentagrophytes, T. rubrum, T. schoenleinii, and T. soudanense. Thus, data reported here showed that Trichophyton susceptibility to ketoconazole and itraconazole could be notably improved by ligustilde and butylidene phthalide. ..
  40. Fukuyama T, Tajima Y, Ueda H, Hayashi K, Kosaka T. Prior exposure to immunosuppressive organophosphorus or organochlorine compounds aggravates the T(H)1- and T(H)2-type allergy caused by topical sensitization to 2,4-dinitrochlorobenzene and trimellitic anhydride. J Immunotoxicol. 2011;8:170-82 pubmed publisher
    ..According to our results, T(H)1- and T(H)2-type allergies are aggravated by prior exposure to immunosuppressive environmental chemicals. ..
  41. Vandebriel R, De Jong W, Spiekstra S, van Dijk M, Fluitman A, Garssen J, et al. Assessment of preferential T-helper 1 or T-helper 2 induction by low molecular weight compounds using the local lymph node assay in conjunction with RT-PCR and ELISA for interferon-gamma and interleukin-4. Toxicol Appl Pharmacol. 2000;162:77-85 pubmed
  42. Vohr H, Pauluhn J, Ahr H. Respiratory hypersensitivity to trimellitic anhydride in Brown Norway rats: evidence for different activation pattern of immune cells following topical and respiratory induction. Arch Toxicol. 2002;76:538-44 pubmed
  43. Hopkins J, Naisbitt D, Humphreys N, Dearman R, Kimber I, Park B. Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Toxicology. 2005;206:221-31 pubmed
  44. Meng Q, Li M. Nickel/zinc-catalyzed decarbonylative addition of anhydrides to alkynes: a DFT study. J Mol Model. 2013;19:4545-54 pubmed publisher
    ..theory (DFT) was used to investigate the nickel- or nickel(0)/zinc- catalyzed decarbonylative addition of phthalic anhydrides to alkynes...
  45. Larsen C, Regal J. Trimellitic anhydride-induced cellular infiltration into Guinea pig lung varies with age but not gender. Int Arch Allergy Immunol. 2002;127:63-72 pubmed
    ..We hypothesized that the TMA-induced allergic response in immature guinea pigs was similar to mature animals, regardless of gender...
  46. Yokota K, Johyama Y, Kunitani Y, Michitsuji H, Yamada S. Methyltetrahydrophthalic acid in urine as an indicator of occupational exposure to methyltetrahydrophthalic anhydride. Int Arch Occup Environ Health. 2005;78:413-7 pubmed
    ..To investigate whether methyltetrahydrophthalic acid (MTHP acid) in urine can be used as a biomarker for exposure to methyltetrahydrophthalic anhydride (MTHPA)...
  47. Le Crom B, Castaings M. Shear horizontal guided wave modes to infer the shear stiffness of adhesive bond layers. J Acoust Soc Am. 2010;127:2220-30 pubmed publisher
  48. Kim J, Go J, Koh E, Song S, Sung J, Lee H, et al. Diosgenin effectively suppresses skin inflammation induced by phthalic anhydride in IL-4/Luc/CNS-1 transgenic mice. Biosci Biotechnol Biochem. 2016;80:891-901 pubmed publisher
  49. Brilakis H, Hann C, Johnson D. A comparison of different embedding media on the ultrastructure of the trabecular meshwork. Curr Eye Res. 2001;22:235-44 pubmed
  50. Kawakami H, Hiraka K, Nagaoka S, Suzuki Y, Iwaki M. Neuronal attachment and outgrowth on a micropatterned fluorinated polyimide surface. J Artif Organs. 2004;7:83-90 pubmed
    ..This initial study indicated enhanced neurite outgrowth and differentiation of PC12 cells on fluorinated polyimide film micropatterned by ion irradiation...
  51. Wang Y, Liang Y, Chen B, He Y, Li B, Hu Q. LC-DAD-APCI-MS-based screening and analysis of the absorption and metabolite components in plasma from a rabbit administered an oral solution of danggui. Anal Bioanal Chem. 2005;383:247-54 pubmed
    ..The results prove that the proposed method can be used to rapidly analyze multiple constituents in TCMs, and to screen for bioactive compounds by comparing and contrasting the chromatographic fingerprints of DOS and plasma samples...
  52. Chai O, Lee H, Lee Y, Lee M, Han E, Kim H, et al. Roles of TNF-alpha and IgE in the late phase of contact hypersensitivity induced by trimellitic anhydride. Exp Mol Med. 2005;37:408-17 pubmed
    ..Neutralization of TNF-alpha and IgE by anti-TNF-alpha or anti-IgE antibodies may provide therapeutic tools for the treatment of TMA-induced CHS...
  53. Li M, Duan J, Qiu J, Yu F, Che X, Jiang S, et al. 3-hydroxyphthalic anhydride-modified human serum albumin as a microbicide candidate against HIV type 1 entry by targeting both viral envelope glycoprotein gp120 and cellular receptor CD4. AIDS Res Hum Retroviruses. 2013;29:1455-64 pubmed publisher
    ..These results suggest that HP-HSA inhibits HIV-1 entry into the target cell by interacting with viral Env gp120 and/or the cellular CD4 receptor, making it a promising microbicide candidate for preventing HIV-1 sexual transmission...
  54. Wei B, Holford Strevens V, Carter B, Sehon A. Suppression of the anti-trimellityl (TM) IgE response in mice by conjugates of TM with polyvinyl alcohol. Immunology. 1984;51:687-96 pubmed
    ..These findings indicate that these conjugates may have the potential of useful therapeutic agents for the treatment of TMA-induced pulmonary hypersensitivity diseases...
  55. Hayashi M, Higashi K, Kato H, Kaneko H. Assessment of preferential Th1 or Th2 induction by low-molecular-weight compounds using a reverse transcription-polymerase chain reaction method: comparison of two mouse strains, C57BL/6 and BALB/c. Toxicol Appl Pharmacol. 2001;177:38-45 pubmed
    ..The results of the present study demonstrate, for the first time, that differential expression of IL-12p40 and IL-4 in C57BL/6 mice may be useful as a parameter for assessing influence of contact and respiratory allergens...
  56. Pauluhn J, Eidmann P, Freyberger A, Wasinska Kempka G, Vohr H. Respiratory hypersensitivity to trimellitic anhydride in Brown Norway rats: a comparison of endpoints. J Appl Toxicol. 2002;22:89-97 pubmed
    ..However, it remains unresolved whether the marked effects observed in the topically sensitized rats are more related to a route-of-induction or dose-dependent phenomenon...
  57. Vandebriel R, De Jong W, Hendriks J, Van Loveren H. Impact of exposure duration by low molecular weight compounds on interferon-gamma and interleukin-4 mRNA expression and production in the draining lymph nodes of mice. Toxicology. 2003;188:1-13 pubmed
    ..Compounds that induce cell proliferation with a low concomitant IL-4 production may thus be identified as contact allergens, although the need to positively identity such allergens remain...
  58. Yokota K, Johyama J, Yamaguchi K, Takeshita T, Morimoto K. The relationship of atopy, smoking, and sensitization to methyltetrahydrophthalic anhydride. Int J Immunopathol Pharmacol. 2004;17:83-90 pubmed
    ..These results suggest that atopic subjects and non-atopic smokers are at increased rist of sensitization by P<0.01. However, to evaluate conclusively the effect of atopy on sensitization, further prospective studies are necessary...
  59. Yeni Y, Yerramshetty J, Akkus O, Pechey C, Les C. Effect of fixation and embedding on Raman spectroscopic analysis of bone tissue. Calcif Tissue Int. 2006;78:363-71 pubmed
    ..It may be necessary to process multiple samples from the tissue, each using a combination appropriate for the Raman parameter in question...
  60. Jellema K, Bleys R, Tijssen C, Koudstaal P, van Gijn J. Thoracic radicular vessels by simultaneous intra-arterial and intravenous injection of araldite. Clin Anat. 2007;20:524-9 pubmed
    ..We found a total of six thoracic arteriovenous shunts in four cadavers but their role in the pathogenesis of SDAVF remains uncertain. No vascular anatomic differences between men and women were found...
  61. Teshima K, Kondo T. Analytical method for determination of allylic isoprenols in rat tissues by liquid chromatography/tandem mass spectrometry following chemical derivatization with 3-nitrophtalic anhydride. J Pharm Biomed Anal. 2008;47:560-6 pubmed publisher
    ..3 and 10.2%, respectively. This method provided reliable concentration levels for farnesol and geranylgeraniol in rat liver and testis...
  62. Nielsen J, Welinder H, Jonsson B, Axmon A, Rylander L, Skerfving S. Exposure to hexahydrophthalic and methylhexahydrophthalic anhydrides--dose-response for sensitization and airway effects. Scand J Work Environ Health. 2001;27:327-34 pubmed
  63. Grammer L, Ditto A, Tripathi A, Harris K. Prevalence and onset of rhinitis and conjunctivitis in subjects with occupational asthma caused by trimellitic anhydride (TMA). J Occup Environ Med. 2002;44:1179-81 pubmed
    ..In summary, symptoms of rhinitis and conjunctivitis are common in subjects with occupational asthma because of TMA and often precede the respiratory symptoms...
  64. Ahlfors S, Kristiansson M, Lindh C, Jönsson B, Hansson C. Adducts between nucleophilic amino acids and hexahydrophthalic anhydride, a structure inducing both types I and IV allergy. Biomarkers. 2005;10:321-35 pubmed
    ..The results will be useful for understanding the formation of HHPA-protein adducts with the capability of being markers of exposure, and also to a deeper understanding of the chemical structures causing types I and IV allergy...
  65. Valstar D, Schijf M, Arts J, Kuper C, Nijkamp F, Storm G, et al. Alveolar macrophages suppress non-specific inflammation caused by inhalation challenge with trimellitic anhydride conjugated to albumin. Arch Toxicol. 2006;80:561-71 pubmed
    ..Since effects of inhalation challenge with TMA-BSA are partly different from those of TMA, challenge with the latter is to be preferred for hazard identification...
  66. Wang C, Zhang H, Qian Z. [Determination of butylidenephthalide in Ligusticum chuanxiong by HPLC]. Zhongguo Zhong Yao Za Zhi. 2007;32:508-10 pubmed
    ..To determine butylidenephthalide in Ligusticum Chuanxiong with RP-HPLC...
  67. Arts J, Schijf M, Kuper C. Preexposure to amorphous silica particles attenuates but also enhances allergic reactions in trimellitic anhydride-sensitized brown Norway rats. Inhal Toxicol. 2008;20:935-48 pubmed
    ..Thus, a respiratory particulate irritant like SAS can reduce as well as aggravate certain aspects of TMA-induced respiratory allergy...
  68. Tarkowski M, Kur B, Polakowska E, Jabłońska E. Comparative studies of lymph node cell subpopulations and cytokine expression in murine model for testing the potentials of chemicals to induce respiratory sensitization. Int J Occup Med Environ Health. 2008;21:253-62 pubmed publisher
  69. Campbell C, Hassler C, Ko S, Voss M, Guaciaro M, Carter P, et al. Enantioselective synthesis of benzyl (1S,2R,4R)-4-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclohexylcarbamate using an iodolactamization as the key step. J Org Chem. 2009;74:6368-70 pubmed publisher
    ..2.1]octane-6-carboxylate 11. An examination of the reaction mechanism within the 2-step iodolactamization sequence led to the discovery of a single-pot transformation of increased efficiency...
  70. He L, Duan J, Qiu J, Yu F, Liu S, Li L. [Antiviral activity of 3-hydroxyphthalic anhydride-modified ovalbumin against herpes simplex virus 2 in vitro]. Nan Fang Yi Ke Da Xue Xue Bao. 2011;31:1175-8 pubmed
    ..To investigate the antiviral activity of 3-hydroxyphthalic anhydride-modified ovalbumin (HP-OVA) against herpes simplex virus 2 (HSV-2) in vitro...
  71. Afroz S, Tripathi A, Chand P, Shanker R. Stress pattern generated by different post and core material combinations: a photoelastic study. Indian J Dent Res. 2013;24:93-7 pubmed publisher
    ..To analyze the effect of different combinations of post and core materials on stress distribution in dentin of an endodontically treated tooth...
  72. Tilvawala R, Pratt R. Kinetics of action of a two-stage pro-inhibitor of serine ?-lactamases. Biochemistry. 2013;52:7060-70 pubmed publisher
    ..Analogues can be conveniently constructed in situ by reaction of nucleophiles with phthalic anhydrides and then screened for activity. Active hits may then become new leads.
  73. Matsumoto K, Kohno S, Ojima K, Tezuka Y, Kadota S, Watanabe H. Effects of methylenechloride-soluble fraction of Japanese angelica root extract, ligustilide and butylidenephthalide, on pentobarbital sleep in group-housed and socially isolated mice. Life Sci. 1998;62:2073-82 pubmed
    ..These results suggest the contribution of ligustilide and butylidenephthalide to the effect of JAR-E on PB sleep in isolated mice, and implicate central noradrenergic and/or GABA(A) systems in the effects of these components...
  74. Yokota K, Johyama Y, Yamaguchi K. A cross-sectional survey of 32 workers exposed to hexahydrophthalic and methylhexahydrophthalic anhydrides. Ind Health. 2002;40:36-41 pubmed
    ..Therefore, to minimize the risk of sensitization and work-related symptoms, a reduction of exposure during particular tasks with high peak exposures, along with a decrease in mean 8-h time-weighted average exposure, should be achieved...
  75. Arts J, Bloksma N, Leusink Muis T, Kuper C. Respiratory allergy and pulmonary irritation to trimellitic anhydride in Brown Norway rats. Toxicol Appl Pharmacol. 2003;187:38-49 pubmed
    ..Sensitization-dependent functional changes were accompanied by inflammatory changes characteristic of asthma and biochemical evidence of airway damage...
  76. Dearman R, Skinner R, Humphreys N, Kimber I. Methods for the identification of chemical respiratory allergens in rodents: comparisons of cytokine profiling with induced changes in serum IgE. J Appl Toxicol. 2003;23:199-207 pubmed
    ..Cytokine profiling using the BALB/c strain mouse apparently provides a more robust method for the hazard assessment of chemical respiratory allergens...
  77. Kristiansson M, Lindh C, Jonsson B. Correlations between air levels of hexahydrophthalic anhydride (HHPA) and HHPA-adducted albumin tryptic peptides in nasal lavage fluid from experimentally exposed volunteers. Rapid Commun Mass Spectrom. 2004;18:1592-8 pubmed
    ..It was possible to detect exposures below 10 microg/m3 with the method. Thus, these adducted peptides may be used as biomarkers of exposure, which may better estimate the risk than previous biomarkers developed for OAAs...
  78. Arts J, de Koning M, Bloksma N, Kuper C. Respiratory allergy to trimellitic anhydride in rats: concentration-response relationships during elicitation. Inhal Toxicol. 2004;16:259-69 pubmed
    ..2 mg/m3, a value that is well below the irritation concentration. The presence of a NOEL in the sensitized BN rat suggests that assessment of safe human exposure levels is feasible...
  79. de Almeida M, Teixeira F, De Souza M, Amarante G, Alves C, Cardoso S, et al. Thalidomide analogs from diamines: Synthesis and evaluation as inhibitors of TNF-alpha production. Chem Pharm Bull (Tokyo). 2007;55:223-6 pubmed
    ..The inhibition was higher for compounds bearing amino and nitro groups and was modulated by increasing the size of the spacers between the phthalimide groups...
  80. Post K, Singer C, Papapetropoulos S. Cardiac denervation and dysautonomia in Parkinson's disease: a review of screening techniques. Parkinsonism Relat Disord. 2008;14:524-31 pubmed publisher
    ..We give one possible example of such a variable in this paper using heart transplant patients as a model...
  81. Holden N, Bedford P, McCarthy N, Marks N, Ind P, Jowsey I, et al. Dendritic cells from control but not atopic donors respond to contact and respiratory sensitizer treatment in vitro with differential cytokine production and altered stimulatory capacity. Clin Exp Allergy. 2008;38:1148-59 pubmed publisher
    ..Objective We sought to determine the effect of atopic status on the ability of DC to respond to contact and respiratory sensitizer treatment in vitro as DC from atopic donors are believed to promote Th2-type responses...
  82. Mikolasch A, Hessel S, Salazar M, Neumann H, Manda K, Gördes D, et al. Synthesis of new N-analogous corollosporine derivatives with antibacterial activity by laccase-catalyzed amination. Chem Pharm Bull (Tokyo). 2008;56:781-6 pubmed
    ..In this regard we report on the straightforward laccase-catalyzed amination of dihydroxylated arenes with N-analogous corollosporines. In biological assays the obtained amination products are more active than the parent compounds...
  83. Mi H, Hiramoto K, Kujirai K, Ando K, Ikarashi Y, Kikugawa K. Effect of food reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and hydroxyhydroquinone (HHQ), on lipid peroxidation and type IV and I allergy responses of mouse. J Agric Food Chem. 2001;49:4950-5 pubmed
    ..In no cases were additive effects of NO(2) inhalation observable. Allergen-sensitized type IV and I allergy responses of mice may be enhanced by supplementation of food reductones, DMHF or HHQ...
  84. Ban M, Hettich D. Effect of Th2 cytokine antagonist treatments on chemical-induced allergic response in mice. J Appl Toxicol. 2005;25:239-47 pubmed
    ..These results would significantly enhance our understanding of the Th1/Th2 response induced by chemicals...
  85. Guo T, Auttachoat W, Chi R. Genistein enhancement of respiratory allergen trimellitic anhydride-induced IgE production by adult B6C3F1 mice following in utero and postnatal exposure. Toxicol Sci. 2005;87:399-408 pubmed
    ..Overall, the results demonstrated that GEN differentially modulated the developing immune system in male and female mice, and that more IgE was produced upon exposure to TMA in the adult...
  86. Johannesson G, Kristiansson M, Jonsson B, Lindh C. Evaluation of an immunoaffinity extraction column for enrichment of adducts between human serum albumin and hexahydrophthalic anhydride in plasma. Biomed Chromatogr. 2008;22:327-32 pubmed
    ..15-1.2 nmol conjugate. The evaluation showed that the IAE column had adequate affinity towards the HHPA adducts and that the adducts could be extracted with good recovery and precision from a large volume of plasma...
  87. Bernstein J, Ghosh D, Sublett W, Wells H, Levin L. Is trimellitic anhydride skin testing a sufficient screening tool for selectively identifying TMA-exposed workers with TMA-specific serum IgE antibodies?. J Occup Environ Med. 2011;53:1122-7 pubmed publisher
    ..Trimellitic anhydride (TMA) can elicit specific IgE-mediated immune responses leading to asthma. This single-blinded study investigated the ability of TMA skin testing to identify workers with TMA-serum specific IgE antibodies...
  88. Pang C, Chiu S, Harn H, Zhai W, Lin S, Yang H. Proteomic-based identification of multiple pathways underlying n-butylidenephthalide-induced apoptosis in LNCaP human prostate cancer cells. Food Chem Toxicol. 2013;59:281-8 pubmed publisher
    ..Proteomic data suggested that multiple signaling pathways including FAS-dependent pathway, mitochondrial pathway, and ER stress pathway are involved in the apoptosis induced by BP. ..
  89. Juárez Gómez J, Pérez García F, Ramirez Silva M, Rojas Hernández A, Galán Vidal C, Paez Hernandez M. Solid-contact Hg(II)-selective electrode based on a carbon-epoxy composite containing a new dithiophosphate-based ionophore. Talanta. 2013;114:235-42 pubmed publisher
    ..The electrode was used satisfactorily as indicating electrode during the potentiometric titration of Hg(II) ions with EDTA...
  90. Berkhout B, Derksen G, Back N, Klaver B, de Kruif C, Visser S. Structural and functional analysis of negatively charged milk proteins with anti-HIV activity. AIDS Res Hum Retroviruses. 1997;13:1101-7 pubmed
  91. Minamoto K, Nagano M, Yonemitsu K, Futatsuka M. Allergic contact dermatitis from unsaturated polyester resin consisting of maleic anhydride, phthalic anhydride, ethylene glycol and dicyclopentadiene. Contact Dermatitis. 2002;46:62-3 pubmed
  92. Pundir C, Chauhan N, Jyoti -. Construction of an amperometric ascorbate biosensor using epoxy resin membrane bound Lagenaria siceraria fruit ascorbate oxidase. Artif Cells Blood Substit Immobil Biotechnol. 2011;39:177-84 pubmed publisher
    ..99) between serum ascorbic acid values by standard enzymic colorimetric method and the present method. The enzyme electrode was used for 200 times without considerable loss of activity during the span of 90 days when stored at 4°C...