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Volumn 18, Issue 2, 2005, Pages 382-388

Quinone methide formations in the Cu2+-induced oxidation of a diterpenone catechol and concurrent damage on DNA

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL DERIVATIVE; COPPER; DITERPENONE CATECHOL; DOUBLE STRANDED DNA; HYDROXYL RADICAL; NUCLEIC ACID BASE; QUINONE DERIVATIVE; TERPENE DERIVATIVE; TERPENE QUINONE METHIDE DERIVATIVE; THIOL; UNCLASSIFIED DRUG;

EID: 13844289443     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049703a     Document Type: Article
Times cited : (14)

References (40)
  • 4
    • 0342490612 scopus 로고    scopus 로고
    • New phenolic and quinone-methide triterpenes from Maytenus amazonia
    • Chávez, H., Estevez-Braum, A., Ravelo, A. G., and González, A. G. (1999) New phenolic and quinone-methide triterpenes from Maytenus amazonia. J. Nat. Prod. 62, 434-436.
    • (1999) J. Nat. Prod. , vol.62 , pp. 434-436
    • Chávez, H.1    Estevez-Braum, A.2    Ravelo, A.G.3    González, A.G.4
  • 7
    • 0014407838 scopus 로고
    • Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium Distichum
    • Kupchan, S. M., Karim, A., and Marcks, C. (1968) Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium Distichum. J. Am. Chem. Soc. 90, 5923-5924.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5923-5924
    • Kupchan, S.M.1    Karim, A.2    Marcks, C.3
  • 8
    • 0346734138 scopus 로고    scopus 로고
    • A general strategy for target-promoted alkylation in biological systems
    • Zhou, Q., and Rokita, S. E. (2003) A general strategy for target-promoted alkylation in biological systems. Proc. Natl. Acad. Sci. U.S.A. 26, 15452-15457.
    • (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.26 , pp. 15452-15457
    • Zhou, Q.1    Rokita, S.E.2
  • 10
    • 0024662764 scopus 로고
    • Chemical modifications of biopolymers by quinone methide
    • Peter, M. G. (1989) Chemical modifications of biopolymers by quinone methide. Angew. Chem., Int. Ed. Engl. 28, 555-570.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 555-570
    • Peter, M.G.1
  • 11
    • 0019724691 scopus 로고
    • Naturally occurring quinones as potential bioreductive alkylating agents
    • Moore, H. W., and Czerniak, R. (1981) Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev. 1, 249-280.
    • (1981) Med. Res. Rev. , vol.1 , pp. 249-280
    • Moore, H.W.1    Czerniak, R.2
  • 12
    • 0035086456 scopus 로고    scopus 로고
    • Synthesis of various oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE
    • Yang, Z., Kitano, Y., Chiba, K., Shibata, N., Kurokawa, H., Doi, Y., Arakawa, Y., and Tada, M. (2001) Synthesis of various oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. Bioorg. Med. Chem. 9, 347-356.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 347-356
    • Yang, Z.1    Kitano, Y.2    Chiba, K.3    Shibata, N.4    Kurokawa, H.5    Doi, Y.6    Arakawa, Y.7    Tada, M.8
  • 13
    • 0035119207 scopus 로고    scopus 로고
    • New antifungal "quinone methide" diterpenes from Bobgunnia madagascariensis and study of their interconversion by LC/NMR
    • Schaller, F., Wolfender, J.-L., Hostettmann, K., and Mavi, S. (2001) New antifungal "quinone methide" diterpenes from Bobgunnia madagascariensis and study of their interconversion by LC/NMR. Helv. Chim. Acta 84, 222-229.
    • (2001) Helv. Chim. Acta , vol.84 , pp. 222-229
    • Schaller, F.1    Wolfender, J.-L.2    Hostettmann, K.3    Mavi, S.4
  • 14
    • 0342981512 scopus 로고    scopus 로고
    • DNA strand scission by polycylic hydrocarbon o-quinone: Role of reactive oxygen species, Cu(II)/(I) redox cycling, and o-semiquinone anion radicals
    • Flowers, L., Ohnishi, T., and Penning, T. M. (1997) DNA strand scission by polycylic hydrocarbon o-quinone: Role of reactive oxygen species, Cu(II)/(I) redox cycling, and o-semiquinone anion radicals. Biochemistry 36, 8640-8648.
    • (1997) Biochemistry , vol.36 , pp. 8640-8648
    • Flowers, L.1    Ohnishi, T.2    Penning, T.M.3
  • 15
    • 0034897760 scopus 로고    scopus 로고
    • Site specificity and mechanism of oxidative DNA damage induced by carcinogenic catechol
    • Oikawa, S., Hirosawa, I., Hirakawa, K., and Kawanishi, S. (2001) Site specificity and mechanism of oxidative DNA damage induced by carcinogenic catechol. Carcinogenesis 22, 1239-1245.
    • (2001) Carcinogenesis , vol.22 , pp. 1239-1245
    • Oikawa, S.1    Hirosawa, I.2    Hirakawa, K.3    Kawanishi, S.4
  • 16
    • 0036156570 scopus 로고    scopus 로고
    • Catechol and hydroquinone have different redox properties responsible for their differential DNA-damaging ability
    • Hirakawa, K., Oikawa, S., Hirosawa, I., Hirosu, I., and Kawanishi, S. (2002) Catechol and hydroquinone have different redox properties responsible for their differential DNA-damaging ability. Chem. Res. Toxicol. 15, 76-82.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 76-82
    • Hirakawa, K.1    Oikawa, S.2    Hirosawa, I.3    Hirosu, I.4    Kawanishi, S.5
  • 17
    • 0036231082 scopus 로고    scopus 로고
    • Oxidative DNA damage induced by equinine estrogen metabolites: Role of estrogen receptor α
    • Liu, X., Yao, J., Pisha, E., Yang, Y., Hua, Y., van Breeman, R. B., and Bolton, J. L. (2002) Oxidative DNA damage induced by equinine estrogen metabolites: Role of estrogen receptor α. Chem. Res. Toxicol. 15, 512-519.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 512-519
    • Liu, X.1    Yao, J.2    Pisha, E.3    Yang, Y.4    Hua, Y.5    Van Breeman, R.B.6    Bolton, J.L.7
  • 18
    • 0035659961 scopus 로고    scopus 로고
    • Equine estrogen metabolite 4-hydroxyequilenin induced DNA damage in the rat mammary tissues: Formation of single strand breaks, apurinic sites, stable adducts and oxidized bases
    • Zhang, F., Swanson, S. M., van Breeman, R. B., Liu, X., Yang, Y., Gu, C., and Bolton, J. L. (2001) Equine estrogen metabolite 4-hydroxyequilenin induced DNA damage in the rat mammary tissues: Formation of single strand breaks, apurinic sites, stable adducts and oxidized bases. Chem. Res. Toxicol. 14, 1654-1659.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1654-1659
    • Zhang, F.1    Swanson, S.M.2    Van Breeman, R.B.3    Liu, X.4    Yang, Y.5    Gu, C.6    Bolton, J.L.7
  • 19
    • 0031741669 scopus 로고    scopus 로고
    • Role of quinoids in estrogen carcinogenesis
    • Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. (1998) Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 10, 1113-1127.
    • (1998) Chem. Res. Toxicol. , vol.10 , pp. 1113-1127
    • Bolton, J.L.1    Pisha, E.2    Zhang, F.3    Qiu, S.4
  • 20
    • 0038011183 scopus 로고    scopus 로고
    • Aldehydic DNA lesions induced by catechol estrogen in calf thymus DNA
    • Lin, P.-H., Nakamura, J., Yamaguchi, S., Asakura, S., and Swenberg, J. A. (2003) Aldehydic DNA lesions induced by catechol estrogen in calf thymus DNA. Carcinogenesis 24, 1133-1141.
    • (2003) Carcinogenesis , vol.24 , pp. 1133-1141
    • Lin, P.-H.1    Nakamura, J.2    Yamaguchi, S.3    Asakura, S.4    Swenberg, J.A.5
  • 21
    • 0030911971 scopus 로고    scopus 로고
    • Estrogen-nucleic acid adducts: Reaction of 3,4-estrone o-quinone with nucleic acid bases
    • Akanni, A., Tabakvoic, K., and Abul-Hajj, Y. (1997) Estrogen-nucleic acid adducts: Reaction of 3,4-estrone o-quinone with nucleic acid bases. Chem. Res. Toxicol. 10, 477-481.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 477-481
    • Akanni, A.1    Tabakvoic, K.2    Abul-Hajj, Y.3
  • 22
    • 50549179309 scopus 로고
    • Preparation and behavior of simple quinone methides
    • Filar, L. J., and Winstein, S. (1960) Preparation and behavior of simple quinone methides. Tetrehedron Lett. 25, 9-25.
    • (1960) Tetrehedron Lett. , vol.25 , pp. 9-25
    • Filar, L.J.1    Winstein, S.2
  • 24
    • 0000480555 scopus 로고
    • Chinomethide
    • (Muller, E., and Bayer, O., Eds.), Houben-Weyl, Stuttgart
    • Grünanger, P. (1979) Chinomethide. In Methoden der Organisch Chemie (Muller, E., and Bayer, O., Eds.) Vol. VII/3b, pp 395-521, Houben-Weyl, Stuttgart.
    • (1979) Methoden der Organisch Chemie , vol.7 , Issue.3 B , pp. 395-521
    • Grünanger, P.1
  • 25
    • 0001623803 scopus 로고
    • Quinone methides
    • (Patai, S., Ed.), John Wiley & Sons, New York
    • Wagner, H. U., and Gompper, R. (1974) Quinone methides. In The Chemistry of Quinonoid Compound (Patai, S., Ed.) Vol. 1, pp 1145-1178, John Wiley & Sons, New York.
    • (1974) The Chemistry of Quinonoid Compound , vol.1 , pp. 1145-1178
    • Wagner, H.U.1    Gompper, R.2
  • 26
    • 0028285123 scopus 로고
    • Evidence that 3-allyl-o-quinone spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole
    • Bolton, J. L., Acay, N. M., and Vukomanovic, V. (1994) Evidence that 3-allyl-o-quinone spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 7, 443-450.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 443-450
    • Bolton, J.L.1    Acay, N.M.2    Vukomanovic, V.3
  • 27
    • 0029061720 scopus 로고
    • The influence of the p-alkyl substituent on the isomerization of o-quinones top-quinone methides: Potential bioactivation Mechanism for catechols
    • Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995) The influence of the p-alkyl substituent on the isomerization of o-quinones top-quinone methides: Potential bioactivation Mechanism for catechols. Chem. Res. Toxicol. 8, 537-544.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 537-544
    • Iverson, S.L.1    Hu, L.Q.2    Vukomanovic, V.3    Bolton, J.L.4
  • 29
    • 33646564507 scopus 로고
    • Selective O-demethylation of catechol ethers. Comparison of boron tribromide and iodotrimethylsilane
    • Vickery, E. H., Fahler, L. F., and Eisenbraun, E. J. (1979) Selective O-demethylation of catechol ethers. Comparison of boron tribromide and iodotrimethylsilane. J. Org. Chem. 44, 4444-4446.
    • (1979) J. Org. Chem. , vol.44 , pp. 4444-4446
    • Vickery, E.H.1    Fahler, L.F.2    Eisenbraun, E.J.3
  • 30
    • 0035996332 scopus 로고    scopus 로고
    • Inhibition of cellular enzymes by equine catechol estrogen in human breast cancer cells: Specificity for glutathione S-transferase P1-1
    • Yao, J., Chang, M., Li, Y., Pisha, E., Liu, X., Yan, D., Elguindi, E, C., Blond, S. Y., and Bolton, J. L. (2002) Inhibition of cellular enzymes by equine catechol estrogen in human breast cancer cells: Specificity for glutathione S-transferase P1-1. Chem. Res. Toxicol. 15, 935-942.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 935-942
    • Yao, J.1    Chang, M.2    Li, Y.3    Pisha, E.4    Liu, X.5    Yan, D.6    Elguindi, E.C.7    Blond, S.Y.8    Bolton, J.L.9
  • 31
    • 0024361159 scopus 로고
    • Trapping of transiently formed quinone methide during enzymatic conversion of N-acetyldopamine to N-acetylnorepinephrine
    • Sugumaran, M., Saul, S., and Semensi, V. (1989) Trapping of transiently formed quinone methide during enzymatic conversion of N-acetyldopamine to N-acetylnorepinephrine. FEBS Lett. 252, 135-138.
    • (1989) FEBS Lett. , vol.252 , pp. 135-138
    • Sugumaran, M.1    Saul, S.2    Semensi, V.3
  • 32
    • 0031434490 scopus 로고    scopus 로고
    • Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: Studies utilizing amino acid and peptide models
    • Bolton, J. L., Turnipseed, S. B., and Thompson, J. A. (1997) Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: Studies utilizing amino acid and peptide models. Chem.-Biol. Interact. 107, 185-200.
    • (1997) Chem.-Biol. Interact. , vol.107 , pp. 185-200
    • Bolton, J.L.1    Turnipseed, S.B.2    Thompson, J.A.3
  • 33
    • 0034616315 scopus 로고    scopus 로고
    • Trapping phosphodiester-quinone methide adducts through in situ lactonization
    • Zhou, Q., and Turnbull, K. D. (2000) Trapping phosphodiester-quinone methide adducts through in situ lactonization J. Org. Chem. 65, 2022-2029.
    • (2000) J. Org. Chem. , vol.65 , pp. 2022-2029
    • Zhou, Q.1    Turnbull, K.D.2
  • 34
    • 0033819217 scopus 로고    scopus 로고
    • Human TP53 from the malignant glioma-derived cell lines M059J and M059K has a cancer-associated mutation in exon 8″
    • Anderson, C. W., and Allalunis-Turner, M. J. (2000) Human TP53 from the malignant glioma-derived cell lines M059J and M059K has a cancer-associated mutation in exon 8″. Radiat. Res. 154, 473-476.
    • (2000) Radiat. Res. , vol.154 , pp. 473-476
    • Anderson, C.W.1    Allalunis-Turner, M.J.2
  • 35
    • 0034831054 scopus 로고    scopus 로고
    • Sequence specific delivery of a quinone methide intermediate to the major groove of DNA
    • Zhou, Q., Pande, P., Johnson, A. E., and Rokita, S. E. (2001) Sequence specific delivery of a quinone methide intermediate to the major groove of DNA. Bioorg. Med. Chem. 9, 2347-2354.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 2347-2354
    • Zhou, Q.1    Pande, P.2    Johnson, A.E.3    Rokita, S.E.4
  • 36
    • 0033859747 scopus 로고    scopus 로고
    • DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH
    • Schweigert, N., Acero, J. L., von Gunten, U., Canonica, S., Zehnder, A. J. B., and Eggen, R. I. L. (2000) DNA degradation by the mixture of copper and catechol is caused by DNA-copper-hydroperoxo complexes, probably DNA-Cu(I)OOH. Environ. Sci. Mol. Mutagen. 36, 5-12.
    • (2000) Environ. Sci. Mol. Mutagen. , vol.36 , pp. 5-12
    • Schweigert, N.1    Acero, J.L.2    Von Gunten, U.3    Canonica, S.4    Zehnder, A.J.B.5    Eggen, R.I.L.6
  • 37
    • 35448999106 scopus 로고    scopus 로고
    • Wave Function Inc., Irvine, CA
    • Spartan (2002) Essential, Wave Function Inc., Irvine, CA.
    • (2002) Essential
  • 38
    • 84962467339 scopus 로고    scopus 로고
    • Reaction paths of keto-enol tautomerization of β-diketones
    • Yamabe, S., Tsuchida, N., and Myajima, K. (2004) Reaction paths of keto-enol tautomerization of β-diketones. J. Phys. Chem. A 108, 2750-2757.
    • (2004) J. Phys. Chem. A , vol.108 , pp. 2750-2757
    • Yamabe, S.1    Tsuchida, N.2    Myajima, K.3
  • 39
    • 0344420324 scopus 로고    scopus 로고
    • Oxidative DNA damage induced by benz-[o]anthracene metabolites via redox cycles of quinone and unique nonquinone
    • Seike, K., Murata, M., Oikawa, S., Hiraku, Y., Hirakawa, K., and Kawanishi, S. (2003) Oxidative DNA damage induced by benz-[o]anthracene metabolites via redox cycles of quinone and unique nonquinone. Chem. Res. Toxicol, 16, 1470-1476.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1470-1476
    • Seike, K.1    Murata, M.2    Oikawa, S.3    Hiraku, Y.4    Hirakawa, K.5    Kawanishi, S.6
  • 40
    • 0014644805 scopus 로고
    • Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium Distichum
    • Kupchan, S. M., Karim, A., and Marcks, C. (1969) Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium Distichum. J. Org. Chem. 34, 3912-3918.
    • (1969) J. Org. Chem. , vol.34 , pp. 3912-3918
    • Kupchan, S.M.1    Karim, A.2    Marcks, C.3


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