메뉴 건너뛰기




Volumn 8, Issue 2, 2004, Pages 175-181

Bleomycins: New methods will allow reinvestigation of old issues

Author keywords

3 PG 5 P; 3 phosphoglycolate, 5 phosphate lesion; Bleomycin; BLM; Double stranded; ds; Electron nuclear double resonance; ENDOR; Phleomycin; PLM; Single stranded; ss

Indexed keywords

BLEOMYCIN;

EID: 1842426944     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2004.02.008     Document Type: Review
Times cited : (63)

References (39)
  • 1
    • 0034827655 scopus 로고    scopus 로고
    • Bleomycin-induced pneumonitis
    • Sleijfer S. Bleomycin-induced pneumonitis. Chest. 120:2001;617-624.
    • (2001) Chest , vol.120 , pp. 617-624
    • Sleijfer, S.1
  • 2
    • 11544259897 scopus 로고    scopus 로고
    • Cleavage of nucleic acids by bleomycin
    • Burger R.M. Cleavage of nucleic acids by bleomycin. Chem Rev. 98:1998;1153-1169.
    • (1998) Chem Rev , vol.98 , pp. 1153-1169
    • Burger, R.M.1
  • 3
    • 0033558171 scopus 로고    scopus 로고
    • Bleomycin: Synthetic and mechanistic studies
    • Boger D.L., Cai H. Bleomycin: synthetic and mechanistic studies. Angew Chem Int Ed Engl. 38:1999;449-476.
    • (1999) Angew Chem Int Ed Engl , vol.38 , pp. 449-476
    • Boger, D.L.1    Cai, H.2
  • 4
    • 0000357885 scopus 로고    scopus 로고
    • Nucleic acid recognition by metal complexes of bleomycin
    • Claussen C.A., Long E.C. Nucleic acid recognition by metal complexes of bleomycin. Chem Rev. 99:1999;2797-2816.
    • (1999) Chem Rev , vol.99 , pp. 2797-2816
    • Claussen, C.A.1    Long, E.C.2
  • 5
    • 0030591651 scopus 로고    scopus 로고
    • DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: Bleomycin, neocarzinostatin and other enediynes
    • Povirk L.F. DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: bleomycin, neocarzinostatin and other enediynes. Mutat Res. 355:1996;71-89.
    • (1996) Mutat Res , vol.355 , pp. 71-89
    • Povirk, L.F.1
  • 6
    • 0037259429 scopus 로고    scopus 로고
    • RNA cleavage and inhibition of protein synthesis by bleomycin
    • BLM can cleave selected members of rRNA, mRNA and tRNA. This paper demonstrates the correlation of protein synthesis inhibition with RNA cleavage, suggesting a new mode of cytotoxicity.
    • Abraham A.T., Lin J.J., Newton D.L., Rybak S., Hecht S.M. RNA cleavage and inhibition of protein synthesis by bleomycin. Chem Biol. 10:2003;45-52 BLM can cleave selected members of rRNA, mRNA and tRNA. This paper demonstrates the correlation of protein synthesis inhibition with RNA cleavage, suggesting a new mode of cytotoxicity.
    • (2003) Chem Biol , vol.10 , pp. 45-52
    • Abraham, A.T.1    Lin, J.J.2    Newton, D.L.3    Rybak, S.4    Hecht, S.M.5
  • 7
    • 0037018482 scopus 로고    scopus 로고
    • Deglycobleomycin: Solid-phase synthesis and DNA cleavage by the resin-bound ligand
    • Smith K.L., Tao Z.F., Hashimoto S., Leitheiser C.J., Wu X., Hecht S.M. Deglycobleomycin: solid-phase synthesis and DNA cleavage by the resin-bound ligand. Org Lett. 4:2002;1079-1082.
    • (2002) Org Lett , vol.4 , pp. 1079-1082
    • Smith, K.L.1    Tao, Z.F.2    Hashimoto, S.3    Leitheiser, C.J.4    Wu, X.5    Hecht, S.M.6
  • 8
    • 0033980083 scopus 로고    scopus 로고
    • Bleomycin: New perspectives on the mechanism of action
    • Hecht S.M. Bleomycin: new perspectives on the mechanism of action. J Nat Prod. 63:2000;158-168.
    • (2000) J Nat Prod , vol.63 , pp. 158-168
    • Hecht, S.M.1
  • 9
    • 0037032261 scopus 로고    scopus 로고
    • Solid-phase synthesis of bleomycin A(5) and three monosaccharide analogues: Exploring the role of the carbohydrate moiety in RNA cleavage
    • Thomas C.J., Chizhov A.O., Leitheiser C.J., Rishel M.J., Konishi K., Tao Z.F., Hecht S.M. Solid-phase synthesis of bleomycin A(5) and three monosaccharide analogues: exploring the role of the carbohydrate moiety in RNA cleavage. J Am Chem Soc. 124:2002;12926-12927.
    • (2002) J Am Chem Soc , vol.124 , pp. 12926-12927
    • Thomas, C.J.1    Chizhov, A.O.2    Leitheiser, C.J.3    Rishel, M.J.4    Konishi, K.5    Tao, Z.F.6    Hecht, S.M.7
  • 10
    • 0002746148 scopus 로고    scopus 로고
    • Bleomycins: A structural model for specificity, binding, and double strand cleavage
    • Stubbe J., Kozarich J.W., Wu W., Vanderwall D.E. Bleomycins: A structural model for specificity, binding, and double strand cleavage. Acc Chem Res. 29:1996;322-330.
    • (1996) Acc Chem Res , vol.29 , pp. 322-330
    • Stubbe, J.1    Kozarich, J.W.2    Wu, W.3    Vanderwall, D.E.4
  • 11
    • 0032538002 scopus 로고    scopus 로고
    • A systematic evaluation of the bleomycin A(2) L-threonine side chain: Its role in preorganization of a compact conformation implicated in sequence-selective DNA cleavage
    • Boger D.L., Ramsey T.M., Cai H., Hoehn S.T., Stubbe J.A. A systematic evaluation of the bleomycin A(2) L-threonine side chain: Its role in preorganization of a compact conformation implicated in sequence-selective DNA cleavage. J Am Chem Soc. 120:1998;9139-9148.
    • (1998) J Am Chem Soc , vol.120 , pp. 9139-9148
    • Boger, D.L.1    Ramsey, T.M.2    Cai, H.3    Hoehn, S.T.4    Stubbe, J.A.5
  • 12
    • 0032538003 scopus 로고    scopus 로고
    • Definition of the effect and role of the bleomycin A(2) valerate substituents: Preorganization of a rigid, compact conformation implicated in sequence-selective DNA cleavage
    • Boger D.L., Ramsey T.M., Cai H., Hoehn S.T., Stubbe J. Definition of the effect and role of the bleomycin A(2) valerate substituents: preorganization of a rigid, compact conformation implicated in sequence-selective DNA cleavage. J Am Chem Soc. 120:1998;9149-9158.
    • (1998) J Am Chem Soc , vol.120 , pp. 9149-9158
    • Boger, D.L.1    Ramsey, T.M.2    Cai, H.3    Hoehn, S.T.4    Stubbe, J.5
  • 13
    • 0033835373 scopus 로고    scopus 로고
    • The biosynthetic gene cluster for the antitumor drug bleomycin from Streptomyces verticillus ATCC15003 supporting functional interactions between nonribosomal peptide synthetases and a polyketide synthase
    • The discovery of the long-sought genes for the biosynthesis of BLM offers new opportunities for investigation of the role of the carbohydrate moiety of BLMs.
    • Du L., Sanchez C., Chen M., Edwards D.J., Shen B. The biosynthetic gene cluster for the antitumor drug bleomycin from Streptomyces verticillus ATCC15003 supporting functional interactions between nonribosomal peptide synthetases and a polyketide synthase. Chem Biol. 7:2000;623-642 The discovery of the long-sought genes for the biosynthesis of BLM offers new opportunities for investigation of the role of the carbohydrate moiety of BLMs.
    • (2000) Chem Biol , vol.7 , pp. 623-642
    • Du, L.1    Sanchez, C.2    Chen, M.3    Edwards, D.J.4    Shen, B.5
  • 14
    • 0030956956 scopus 로고    scopus 로고
    • 1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose
    • Wittmann V., Wong C.H. 1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose. J Org Chem. 62:1997;2144-2147.
    • (1997) J Org Chem , vol.62 , pp. 2144-2147
    • Wittmann, V.1    Wong, C.H.2
  • 15
    • 0037109032 scopus 로고    scopus 로고
    • Expanding pyrimidine diphosphosugar libraries via structure-based nucleotidylyltransferase engineering
    • Barton W.A., Biggins J.B., Jiang J., Thorson J.S., Nikolov D.B. Expanding pyrimidine diphosphosugar libraries via structure-based nucleotidylyltransferase engineering. Proc Natl Acad Sci USA. 99:2002;13397-13402.
    • (2002) Proc Natl Acad Sci USA , vol.99 , pp. 13397-13402
    • Barton, W.A.1    Biggins, J.B.2    Jiang, J.3    Thorson, J.S.4    Nikolov, D.B.5
  • 17
    • 0025250121 scopus 로고
    • The role of redox-active metals in the mechanism of action of bleomycin
    • Petering D.H., Byrnes R.W., Antholine W.E. The role of redox-active metals in the mechanism of action of bleomycin. Chem Biol Interact. 73:1990;133-182.
    • (1990) Chem Biol Interact , vol.73 , pp. 133-182
    • Petering, D.H.1    Byrnes, R.W.2    Antholine, W.E.3
  • 18
    • 0038390597 scopus 로고    scopus 로고
    • 15N] HSQC NMR investigation of bleomycin, deglycobleomycin, and their hydroperoxide-cobalt(III) complexes
    • 3+-OOH, negating interpretation of earlier studies on Co(III)-pepleomycin [39].
    • 3+-OOH, negating interpretation of earlier studies on Co(III)-pepleomycin [39].
    • (2003) Biochemistry , vol.42 , pp. 6559-6564
    • Xia, C.1    Forsterling, F.H.2    Petering, D.H.3
  • 21
    • 0036933220 scopus 로고    scopus 로고
    • Molecular modeling of the three-dimensional structure of Fe(II)-bleomycin: Are the Co(II) and Fe(II) adducts isostructural?
    • Lehmann T.E. Molecular modeling of the three-dimensional structure of Fe(II)-bleomycin: are the Co(II) and Fe(II) adducts isostructural? J Biol Inorg Chem. 7:2002;305-312.
    • (2002) J Biol Inorg Chem , vol.7 , pp. 305-312
    • Lehmann, T.E.1
  • 23
    • 0030981907 scopus 로고    scopus 로고
    • Fe- and Co-bleomycins bound to site specific and nonspecific DNA decamers: Comparative binding and reactivity of their metal centers
    • Fulmer P., Zhao C., Li W., DeRose E., Antholine W.E., Petering D.H. Fe- and Co-bleomycins bound to site specific and nonspecific DNA decamers: comparative binding and reactivity of their metal centers. Biochemistry. 36:1997;4367-4374.
    • (1997) Biochemistry , vol.36 , pp. 4367-4374
    • Fulmer, P.1    Zhao, C.2    Li, W.3    Derose, E.4    Antholine, W.E.5    Petering, D.H.6
  • 24
    • 0032542563 scopus 로고    scopus 로고
    • Spectroscopic investigation of the metal ligation and reactivity of the ferrous active sites of bleomycin and bleomycin derivatives
    • Loeb K.E., Zaleski J.M., Hess C.D., Hecht S.M., Solomon E.I. Spectroscopic investigation of the metal ligation and reactivity of the ferrous active sites of bleomycin and bleomycin derivatives. J Am Chem Soc. 120:1998;1249-1259.
    • (1998) J Am Chem Soc , vol.120 , pp. 1249-1259
    • Loeb, K.E.1    Zaleski, J.M.2    Hess, C.D.3    Hecht, S.M.4    Solomon, E.I.5
  • 26
    • 0034731019 scopus 로고    scopus 로고
    • Electronic structure of activated bleomycin: Oxygen intermediates in heme versus non-heme iron
    • Neese F., Zaleski J.M., Zaleski K.L., Solomon E.I. Electronic structure of activated bleomycin: oxygen intermediates in heme versus non-heme iron. J Am Chem Soc. 122:2000;11703-11724.
    • (2000) J Am Chem Soc , vol.122 , pp. 11703-11724
    • Neese, F.1    Zaleski, J.M.2    Zaleski, K.L.3    Solomon, E.I.4
  • 27
    • 0037063569 scopus 로고    scopus 로고
    • Electronic structure and reactivity of low-spin Fe(III)-hydroperoxo complexes: Comparison to activated bleomycin
    • Calculations in an effort to guide thinking about the reactivity of low spin non-heme iron peroxides.
    • Lehnert N., Neese F., Ho R.Y., Que L. Jr., Solomon E.I. Electronic structure and reactivity of low-spin Fe(III)-hydroperoxo complexes: comparison to activated bleomycin. J Am Chem Soc. 124:2002;10810-10822 Calculations in an effort to guide thinking about the reactivity of low spin non-heme iron peroxides.
    • (2002) J Am Chem Soc , vol.124 , pp. 10810-10822
    • Lehnert, N.1    Neese, F.2    Ho, R.Y.3    Que, L.Jr.4    Solomon, E.I.5
  • 29
    • 0038747011 scopus 로고    scopus 로고
    • The first direct characterization of a high-valent iron intermediate in the reaction of an alpha-ketoglutarate-dependent dioxygenase: A high-spin FeIV complex in taurine/alpha-ketoglutarate dioxygenase (TauD) from Escherichia coli
    • Price J.C., Barr E.W., Tirupati B., Bollinger J.M. Jr., Krebs C. The first direct characterization of a high-valent iron intermediate in the reaction of an alpha-ketoglutarate-dependent dioxygenase: a high-spin FeIV complex in taurine/alpha-ketoglutarate dioxygenase (TauD) from Escherichia coli. Biochemistry. 42:2003;7497-7508.
    • (2003) Biochemistry , vol.42 , pp. 7497-7508
    • Price, J.C.1    Barr, E.W.2    Tirupati, B.3    Bollinger, J.M.Jr.4    Krebs, C.5
  • 30
    • 0035850519 scopus 로고    scopus 로고
    • 2. Efficient, double-strand DNA cleavage accessible without structural reorganization
    • 2. Efficient, double-strand DNA cleavage accessible without structural reorganization. J Am Chem Soc. 123:2001;8690-8700.
    • (2001) J Am Chem Soc , vol.123 , pp. 8690-8700
    • Keck, M.V.1    Manderville, R.A.2    Hecht, S.M.3
  • 31
    • 0035918531 scopus 로고    scopus 로고
    • Solution structure of Co(III)-bleomycin-OOH bound to a phosphoglycolate lesion containing oligonucleotide: Implications for bleomycin-induced double-strand DNA cleavage
    • Hoehn S.T., Junker H.D., Bunt R.C., Turner C.J., Stubbe J. Solution structure of Co(III)-bleomycin-OOH bound to a phosphoglycolate lesion containing oligonucleotide: implications for bleomycin-induced double-strand DNA cleavage. Biochemistry. 40:2001;5894-5905.
    • (2001) Biochemistry , vol.40 , pp. 5894-5905
    • Hoehn, S.T.1    Junker, H.D.2    Bunt, R.C.3    Turner, C.J.4    Stubbe, J.5
  • 32
    • 0032486797 scopus 로고    scopus 로고
    • Characterization of Zn(II)-deglycobleomycin A(2) and interaction with d(CGCTAGCG)(2): Direct evidence for minor groove binding of the bithiazole moiety
    • Sucheck S.J., Ellena J.F., Hecht S.M. Characterization of Zn(II)-deglycobleomycin A(2) and interaction with d(CGCTAGCG)(2): direct evidence for minor groove binding of the bithiazole moiety. J Am Chem Soc. 120:1998;7450-7460.
    • (1998) J Am Chem Soc , vol.120 , pp. 7450-7460
    • Sucheck, S.J.1    Ellena, J.F.2    Hecht, S.M.3
  • 33
    • 0034801244 scopus 로고    scopus 로고
    • Metallobleomycin-mediated cleavage of DNA not involving a threading-intercalation mechanism
    • Abraham A.T., Zhou X., Hecht S.M. Metallobleomycin-mediated cleavage of DNA not involving a threading-intercalation mechanism. J Am Chem Soc. 123:2001;5167-5175.
    • (2001) J Am Chem Soc , vol.123 , pp. 5167-5175
    • Abraham, A.T.1    Zhou, X.2    Hecht, S.M.3
  • 34
    • 18744398387 scopus 로고    scopus 로고
    • 2: Evidence for binding by partial intercalation
    • This article demonstrates that phleomycin (PLM) binds by partial intercalation, despite the fact that the penultimate thiazolium ring is partially reduced. Thus, the observation that PLM and BLM cleave DNA in vivo with similar efficiency does not negate the importance of the intercalative mode of binding of BLMs.
    • 2: evidence for binding by partial intercalation. Nucleic Acids Res. 30:2002;4881-4891 This article demonstrates that phleomycin (PLM) binds by partial intercalation, despite the fact that the penultimate thiazolium ring is partially reduced. Thus, the observation that PLM and BLM cleave DNA in vivo with similar efficiency does not negate the importance of the intercalative mode of binding of BLMs.
    • (2002) Nucleic Acids Res , vol.30 , pp. 4881-4891
    • Wu, W.1    Vanderwall, D.E.2    Turner, C.J.3    Hoehn, S.4    Chen, J.5    Kozarich, J.W.6    Stubbe, J.7
  • 35
    • 0035799885 scopus 로고    scopus 로고
    • Synthesis and DNA cleavage activity of a novel bleomycin A(5) glycoconjugate
    • Choudhury A.K., Tao Z.F., Hecht S.M. Synthesis and DNA cleavage activity of a novel bleomycin A(5) glycoconjugate. Org Lett. 3:2001;1291-1294.
    • (2001) Org Lett , vol.3 , pp. 1291-1294
    • Choudhury, A.K.1    Tao, Z.F.2    Hecht, S.M.3
  • 36
    • 0028923387 scopus 로고
    • Sequence-specific double-strand cleavage of DNA by Fe bleomycin. 2. Mechanism and dynamics
    • Absalon M.J., Wu W., Kozarich J.W., Stubbe J. Sequence-specific double-strand cleavage of DNA by Fe bleomycin. 2. Mechanism and dynamics. Biochemistry. 34:1995;2076-2086.
    • (1995) Biochemistry , vol.34 , pp. 2076-2086
    • Absalon, M.J.1    Wu, W.2    Kozarich, J.W.3    Stubbe, J.4
  • 37
    • 0036913910 scopus 로고    scopus 로고
    • Remarkable structural similarities between diverse glycosyltransferases
    • Hu Y., Walker S. Remarkable structural similarities between diverse glycosyltransferases. Chem Biol. 9:2002;1287-1296.
    • (2002) Chem Biol , vol.9 , pp. 1287-1296
    • Hu, Y.1    Walker, S.2
  • 38
    • 12244297801 scopus 로고    scopus 로고
    • Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides
    • Losey H.C., Jiang J., Biggins J.B., Oberthur M., Ye X.Y., Dong S.D., Kahne D., Thorson J.S., Walsh C.T. Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides. Chem Biol. 9:2002;1305-1314.
    • (2002) Chem Biol , vol.9 , pp. 1305-1314
    • Losey, H.C.1    Jiang, J.2    Biggins, J.B.3    Oberthur, M.4    Ye, X.Y.5    Dong, S.D.6    Kahne, D.7    Thorson, J.S.8    Walsh, C.T.9
  • 39
    • 0030934164 scopus 로고    scopus 로고
    • Structures of cobalt(III)-pepleomycin and cobalt(III)-deglycopepleomycin (green forms) determined by NMR studies
    • Caceres-Cortes J., Sugiyama H., Ikudome K., Saito I., Wang A.H. Structures of cobalt(III)-pepleomycin and cobalt(III)-deglycopepleomycin (green forms) determined by NMR studies. Eur J Biochem. 244:1997;818-828.
    • (1997) Eur J Biochem , vol.244 , pp. 818-828
    • Caceres-Cortes, J.1    Sugiyama, H.2    Ikudome, K.3    Saito, I.4    Wang, A.H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.