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Chemical Compound Review

PHENOTAZINE     10H-phenoxazine

Synonyms: Phenazoxine, Phenoxazine, SureCN7862, CHEMBL276850, P14858_ALDRICH, ...
 
 
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Disease relevance of NSC72990

 

High impact information on NSC72990

  • The phenoxazine/C-5 propynyl U 7-mer S-ON showed dose-dependent, sequence-specific, and target-selective antisense activity following microinjection into cells [5].
  • Using a structure-based drug design approach ortho-trifluormethylphenyl anthranilic acid and N-(meta-trifluoromethylphenyl) phenoxazine 4, 6-dicarboxylic acid have been discovered to be very potent and specific TTR fibril formation inhibitors [6].
  • Antitumor effects of a novel phenoxazine derivative on human leukemia cell lines in vitro and in vivo [7].
  • It is concluded that at least part of the activity of some of these N-substituted phenoxazine modulators may be mediated through a P-glycoprotein-independent mechanism [8].
  • The linkers were designed based on the attachment sites at two different positions on the phenoxazine, which were chosen in order to study the orientation of the dye with respect to the binding protein [9].
 

Chemical compound and disease context of NSC72990

 

Biological context of NSC72990

 

Anatomical context of NSC72990

  • A novel phenoxazine derivative suppresses surface IgM expression in DT40 B cell line [18].
  • We have demonstrated that the treatment of rat mast cells, RBL-2H3, with a phenoxazine derivative Phx-1 (2-amino-4,4alpha-dihydro-4alpha,7-dimethyl-3H-phenoxazine-3-one) suppresses the antigen-induced degranulation [19].
  • A phenoxazine compound, 2-amino-4,4alpha-dihydro-4alpha-7-dimethyl-3H-phenoxazine-3-one reverses the phenylephrine or high-K+ induced contraction of smooth muscles in rat aorta and guinea pig tenia cecum [20].
 

Associations of NSC72990 with other chemical compounds

  • Further, phenoxazine decreased the efflux of VLB by 30% in KB-ChR-8-5 cell line and 10% in GC3/C1 cells [21].
  • BACKGROUND: Fluorescent biosensors based on galactose/glucose binding protein (GGBP) and environmentally sensitive derivatives of the phenoxazine dye Nile Red are described [22].
  • The ESR spectroscopy showed that the reduction of these complexes with P(PhX)3 (X = H, m-Cl, m-CH3, p-Et2N-) and 1,4-bis(diphenyldiphosphino) butane (dppb) proceeds via the radical formation (phenoxazine, amino phenoxy and nitrene type radical intermediates) and pathways of reduction depend on the structure of these complexes [23].
 

Gene context of NSC72990

 

Analytical, diagnostic and therapeutic context of NSC72990

  • Synthesis of thiol-reactive, long-wavelength fluorescent phenoxazine derivatives for biosensor applications [9].
  • In the PN-induced and TPA-promoted two-stage mouse skin carcinogenesis, oral administration of phenoxazine (0.0025%) for 2 weeks showed profound decrease in both the tumor incidence and burden by more than 20 and 80%, respectively, at 10 weeks of treatment [12].

References

  1. Photosensitization, uptake, and retention of phenoxazine Nile blue derivatives in human bladder carcinoma cells. Lin, C.W., Shulok, J.R., Wong, Y.K., Schanbacher, C.F., Cincotta, L., Foley, J.W. Cancer Res. (1991) [Pubmed]
  2. Chlamydia pneumoniae growth inhibition in human monocytic THP-1 cells and human epithelial HEp-2 cells by a novel phenoxazine derivative. Uruma, T., Yamaguchi, H., Fukuda, M., Kawakami, H., Goto, H., Kishimoto, T., Yamamoto, Y., Tomoda, A., Kamiya, S. J. Med. Microbiol. (2005) [Pubmed]
  3. Caspase-independent cell death revealed in human gastric cancer cell lines, MKN45 and KATO III treated with phenoxazine derivatives. Kasuga, T., Tabuchi, T., Shirato, K., Imaizumi, K., Tomoda, A. Oncol. Rep. (2007) [Pubmed]
  4. Isolation and structure of a new phenoxazine antibiotic, exfoliazone, produced by Streptomyces exfoliatus. Imai, S., Shimazu, A., Furihata, K., Furihata, K., Hayakawa, Y., Seto, H. J. Antibiot. (1990) [Pubmed]
  5. Cellular penetration and antisense activity by a phenoxazine-substituted heptanucleotide. Flanagan, W.M., Wagner, R.W., Grant, D., Lin, K.Y., Matteucci, M.D. Nat. Biotechnol. (1999) [Pubmed]
  6. Rational design of potent human transthyretin amyloid disease inhibitors. Klabunde, T., Petrassi, H.M., Oza, V.B., Raman, P., Kelly, J.W., Sacchettini, J.C. Nat. Struct. Biol. (2000) [Pubmed]
  7. Antitumor effects of a novel phenoxazine derivative on human leukemia cell lines in vitro and in vivo. Shimamoto, T., Tomoda, A., Ishida, R., Ohyashiki, K. Clin. Cancer Res. (2001) [Pubmed]
  8. Pharmacological characterization of N-substituted phenoxazines directed toward reversing Vinca alkaloid resistance in multidrug-resistant cancer cells. Horton, J.K., Thimmaiah, K.N., Harwood, F.C., Kuttesch, J.F., Houghton, P.J. Mol. Pharmacol. (1993) [Pubmed]
  9. Synthesis of thiol-reactive, long-wavelength fluorescent phenoxazine derivatives for biosensor applications. Sherman, D.B., Pitner, J.B., Ambroise, A., Thomas, K.J. Bioconjug. Chem. (2006) [Pubmed]
  10. Antitumor activity of 2-amino-4,4 alpha-dihydro-4 alpha, 7-dimethyl-3H-phenoxazine-3-one, a novel phenoxazine derivative produced by the reaction of 2-amino-5-methylphenol with bovine hemolysate. Ishida, R., Yamanaka, S., Kawai, H., Ito, H., Iwai, M., Nishizawa, M., Hamatake, M., Tomoda, A. Anticancer Drugs (1996) [Pubmed]
  11. Free-radical-scavenging effect of carbazole derivatives on AAPH-induced hemolysis of human erythrocytes. Tang, Y.Z., Liu, Z.Q. Bioorg. Med. Chem. (2007) [Pubmed]
  12. Cancer chemopreventive effect of phenothiazines and related tri-heterocyclic analogues in the 12-O-tetradecanoylphorbol-13-acetate promoted Epstein-Barr virus early antigen activation and the mouse skin two-stage carcinogenesis models. Azuine, M.A., Tokuda, H., Takayasu, J., Enjyo, F., Mukainaka, T., Konoshima, T., Nishino, H., Kapadia, G.J. Pharmacol. Res. (2004) [Pubmed]
  13. Kinetics of cellular permeability of phenoxazine and its dependence on P-glycoprotein expression. Wadkins, R.M., Houghton, P.J. FEBS Lett. (1993) [Pubmed]
  14. Antitumor activity of a phenoxazine compound, 2-amino-4,4alpha-dihydro-4alpha,7-dimethyl-3H-phenoxazine-3-one against human B cell and T cell lymphoblastoid cell lines: induction of mixed types of cell death, apoptosis, and necrosis. Koshibu-Koizumi, J., Akazawa, M., Iwamoto, T., Takasaki, M., Mizuno, F., Kobayashi, R., Abe, A., Tomoda, A., Hamatake, M., Ishida, R. J. Cancer Res. Clin. Oncol. (2002) [Pubmed]
  15. Inhibition of calmodulin-dependent cyclic AMP phosphodiesterase by phenoxazines. Jagadeesh, S., Padma, T., Parimala, H., Chandramouli, K.H., D'Souza, C.J., Thimmaiah, K.N. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  16. A novel phenoxazine derivative suppresses proliferation of human endometrial adenocarcinoma cell lines, inducing G2M accumulation and apoptosis. Nakada, T., Isaka, K., Nishi, H., Osakabe, Y., Shimamoto, T., Ohyashiki, K., Tomoda, A., Takayama, M. Oncol. Rep. (2003) [Pubmed]
  17. The percutaneous absorption of triarylmethane and phenoxazine type colour former components of carbonless copy papers. Cameron, B.D., Dunsire, J.P., Draffan, G.H., Bruce, J.C. The Annals of occupational hygiene. (1986) [Pubmed]
  18. A novel phenoxazine derivative suppresses surface IgM expression in DT40 B cell line. Gao, S., Takano, T., Sada, K., He, J., Noda, C., Hori-Tamura, N., Tomoda, A., Yamamura, H. Br. J. Pharmacol. (2002) [Pubmed]
  19. The phenoxazine derivative Phx-1 suppresses IgE-mediated degranulation in rat basophilic leukemia RBL-2H3 cells. Enoki, E., Sada, K., Qu, X., Kyo, S., Miah, S.M., Hatani, T., Tomoda, A., Yamamura, H. J. Pharmacol. Sci. (2004) [Pubmed]
  20. A phenoxazine compound, 2-amino-4,4alpha-dihydro-4alpha-7-dimethyl-3H-phenoxazine-3-one reverses the phenylephrine or high-K+ induced contraction of smooth muscles in rat aorta and guinea pig tenia cecum. Musha, S., Watanabe, M., Ishida, Y., Kato, S., Konishi, M., Tomoda, A. Biol. Pharm. Bull. (2005) [Pubmed]
  21. Structural determinants of phenoxazine type compounds required to modulate the accumulation of vinblastine and vincristine in multidrug-resistant cell lines. Thimmaiah, K.N., Horton, J.K., Qian, X.D., Beck, W.T., Houghton, J.A., Houghton, P.J. Cancer Commun. (1990) [Pubmed]
  22. A long-wavelength fluorescent glucose biosensor based on bioconjugates of galactose/glucose binding protein and Nile Red derivatives. Thomas, K.J., Sherman, D.B., Amiss, T.J., Andaluz, S.A., Pitner, J.B. Diabetes Technol. Ther. (2006) [Pubmed]
  23. Synthesis and ESR studies of redox reactivity of bis (3,5-di-tert-butyl-1,2-benzoquinone-2-monooximato)Cu(II). Kasumov, V.T., Kartal, I., Koksal, F. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2000) [Pubmed]
  24. Synergistic enhancement of TRAIL- and tumor necrosis factor alpha-induced cell death by a phenoxazine derivative. Hara, K., Okamoto, M., Aki, T., Yagita, H., Tanaka, H., Mizukami, Y., Nakamura, H., Tomoda, A., Hamasaki, N., Kang, D. Mol. Cancer Ther. (2005) [Pubmed]
 
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