Solid-phase synthesis of deglycobleomycin and bleomycin

Current Opinion in Drug Discovery and Development

Volumn 6, Issue 6, 2003, Pages 827-837

  Leitheiser, Christopher J ^a   Hecht, Sidney M ^b  

^a University of Minnesota   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Bleomycin; Combinatorial synthesis; Deglycobleomycin; DNA; RNA; Solid phase synthesis

Indexed keywords

BLEOMYCIN; BLEOMYCIN DERIVATIVE; DEGLYCOBLEOMYCIN; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

COMBINATORIAL LIBRARY; DRUG ISOLATION; DRUG SYNTHESIS; HEAD AND NECK CANCER; HODGKIN DISEASE; REACTION ANALYSIS; REVIEW; SKIN CARCINOMA; SOLID STATE; STREPTOMYCES; STREPTOMYCES VERTICILLUS; STRUCTURE ACTIVITY RELATION; TESTIS TUMOR;

ANTI-BACTERIAL AGENTS; BLEOMYCIN; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS; HUMANS;

EID: 0346458779     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (64)

1. Umezawa H, Suhara Y, Takita T, Maeda K: Purification of bleomycins. J Antibiot (1966) (19A):210.
2. Aoyagi Y, Katano K, Suguna H, Primeau J, Chang LH, Hecht SM: Total synthesis of bleomycin. J Am Chem Soc (1982) 104(20):5537-5538.
3. 2. Tetrahedron Lett (1982) 23(5):521-524.
4. 2. J Am Chem Soc (1994) 116(13):5647-5656.
5. 2. J Am Chem Soc (1998) 120(44):11285-11296.
6. Sikic BI, Rozencweig M, Carter SK (Eds): Bleomycin Chemotherapy. Academic Press, Orlando, FL, USA (1985).
7. Powis G (Ed): Anticancer Drugs: Reactive Metabolism and Drug Interactions. Pergamon Press, New York, NY, USA (1994).
8. Hecht SM: The chemistry of activated bleomycin. Acc Chem Res (1986) 19(12):383-391.
9. Stubbe J, Kozarich JW: Mechanisms of bleomycin-induced DNA degradation. Chem Rev (1987) 87(5):1107-1136.
10. Natrajan A, Hecht SM: Bleomycins: Mechanism of polynucleotide recognition and oxidative degradation. In: Molecular Aspects of Anticancer Drug-DNA Interactions. Neidle S, Waring MJ (Eds), Macmillan, London, UK (1994):197-242.
11. Kane SA, Hecht SM: Polynucleotide recognition and degradation by bleomycin. Progr Nucleic Acid Res Mol Biol (1994) 49:313-352.
12. Aso M, Kondo M, Suemune H, Hecht SM: Chemistry of the bleomycin-induced alkali-labile DNA lesion. J Am Chem Soc (1999) 121 (39):9023-9033.
13. Hecht SM: Bleomycin: New perspectives on the mechanism of action. J Nat Prod (2000) 63(1):158-168.
14. D'Andrea AD, Haseltine WA: Sequence specific cleavage of DNA by the antitumor antibiotics neocarzinostatin and bleomycin. Proc Natl. Acad Sci USA (1978) 75(8):3608-3612.
15. Takeshita M, Grollman AP: Interaction of bleomycin with DNA. Proc Natl Acad Sci USA (1978) 75(12):5983-5987.
16. Mirabelli CK, Ting A, Huang CH, Mong S, Crooke ST: Bleomycin and talisomycin sequence-specific strand scission of DNA: A mechanism of double-strand cleavage. Cancer Res (1982) 42(7):2779-2785.
17. Kuwahara J, Sugiura Y: Sequence-specific recognition and cleavage of DNA by metallobleomycin: Minor groove binding and possible interaction mode. Proc Natl Acad Sci USA (1988) 85(8):2459-2463.
18. Bailly C, Waring MJ: The purine 2-amino group as a critical recognition element for specific DNA cleavage by bleomycin and calicheamicin. J Am Chem Soc (1995) 117(28):7311-7316.
19. Hecht SM: RNA degradation by bleomycin, a naturally occurring bioconjugate. Bioconjug Chem (1994) 5(6):513-526.
20. Holmes CE, Duff RJ, van der Marel GA, van Boom J, Hecht SM: On the chemistry of RNA degradation by Febleomycin. Bioorg Med Chem (1997) 5(6):1235-1248.
21. Sugiyama H, Ehrenfeld GM, Shipley JB, Kilkuskie RE, Chang LH, Hecht SM: DNA strand scission by bleomycin group antibiotics. J Nat Prod (1985) 48(6):869-877.
22. Shipley JB, Hecht SM: Bleomycin congeners exhibiting altered DNA cleavage specificity. Chem Res Toxicol (1988) 1(1):25-27.
23. Oppenheimer NJ, Chang C, Chang LH, Ehrenfeld G, Rodriguez LO, Hecht SM: Deglyco-bleomycin. Degradation of DNA and formation of a structurally unique Fe(II).CO complex. J Biol Chem (1982) 257(4):1606-1609.
24. Aoyagi Y, Suguna H, Murugesan N, Ehrenfeld GM, Chang LH, Ohgi T, Shekhani MS, Kirkup MP, Hecht SM: Deglycobleomycin: Total synthesis and oxygen transfer properties of an active bleomycin analog. J Am Chem Soc (1982) 104(19):5237-5239.
25. Sugiura Y, Suzuki T, Otsuka M, Kobayashi S, Ohno M, Takita T, Umezawa H: Synthetic analogues and biosynthetic intermediates of bleomycin. Metal-binding, dioxygen interaction, and implication for the role of functional groups in bleomycin action mechanism. J Biol Chem (1983) 258(2):1328-1336.
26. Umezawa H, Takita T, Sugiura Y, Otsuka M, Kobayashi S, Ohno M: DNA-bleomycin interaction: Nucleotide sequence-specific binding and cleavage of DNA by bleomycin. Tetrahedron (1984) 40(3):501-509.
27. Boger DL, Cai H: Bleomycin: Synthetic and mechanistic studies. Angew Chem Int Ed (1999) 38(4):448-476.
28. 5. Org Lett (2000) 2(21):3397-3399. The initial report of the solid-phase synthesis of deglycobleomycin.
29. Owa T, Haupt A, Otsuka M, Kobayashi S, Nobuo T, Itai A, Ohno M: Man-designed bleomycins: Significance of the binding sites as enzyme models and of the stereochemistry of the linker moiety. Tetrahedron (1992) 48(7):1193-1208.
30. Boger DL, Menezes RF: Synthesis of tri- and tetrapeptide S: The extended C-terminus of bleomycin A2. J Org Chem (1992) 57(16):4331-4333.
31. 2 and related agents. 1. Synthesis and DNA binding properties of the extended C-terminus: Tripeptide S, tetrapeptide S, pentapeptide S, and related agents. J Am Chem Soc (1994) 116(13):5607-5618.
32. Gordeev MF, Luehr GW, Hui HC, Gordon EM, Patel DV: Combinatorial chemistry of natural products: Solid phase synthesis of D- and L-cycloserine derivatives. Tetrahedron (1998) 54(52):15879-15890.
33. 2 analogues containing a tertiary N-methyl amide and simple ester replacement for the L-histidine secondary amide: Direct functional characterization of the requirement for secondary amide metal complexation. Bioorg Med Chem (1996) 4(2):179-193.
34. Nash IA, Bycroft BW, Chan WC: Dde - A selective primary amine protecting group: A facile solid phase synthetic approach to polyamine conjugates. Tetrahedron Lett (1996) 37(15):2625-2368.
35. Bycroft BW, Chan WC, Chhabra SR, Hone ND: A novel lysine-protecting procedure for continuous-flow solid-phase synthesis of branched peptides. Chem Commun (1993) 9:778-779.
36. Knorr R, Trzeciak A, Bannwarth W, Gillessen D: New coupling reagents in peptide chemistry. Tetrahedron Lett (1989) 30(15):1927-1930.
37. Carpino LA: 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J Am Chem Soc (1993) 115(10):4397-4398.
38. Carpino LA, El-Faham A, Minor CA, Albericio F: Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide-synthesis. Chem Commun (1994) 2:201-203.
39. Gawne G, Kenner GW, Sheppard RC: Acyloxyphosphonium salts as acylating agents. Synthesis of peptides. J Am Chem Soc (1969) 91 (20):5669-5671.
40. Castro B, Dormoy JR, Evin G, Selve C: Réactifs de couplage peptidique I (1) - L'hexafluorophosphate de benzotriazolyl N-oxytrisdimethylamino phosphonium (B.O.P.). Tetrahedron Lett (1975) 16(14):1219-1222.
41. Pearson DA, Blanchette M, Baker ML, Guindon CA: Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis. Tetrahedon Lett (1989) 30(21):2739-2742.
42. 2. Carbohydr Res (1988) 177:81-89.
43. Abraham AT, Zhou X, Hecht SM: DNA cleavage by Fe(II).bleomycin conjugated to a solid support. J Am Chem Soc (1999) 121(9):1982-1983.
44. Abraham AT, Zhou X, Hecht SM: Metallobleomycin-mediated cleavage of DNA not involving a threading-intercalation mechanism. J Am Chem Soc (2001) 123(22):5167-5175.
45. Chhabra SR, Khan AN, Bycroft BW: Versatile Dde-based primary amine linkers for solid phase synthesis. Tetrahedron Lett (1998) 39(21):3585-3588.
46. Chhabra SR, Khan AN, Bycroft BW: Solid-phase synthesis of polyamines using a Dde-linker: Philanthotoxin-4.3.3 via an on-resin Mitsunobu reaction. Tetrahedron Lett (2000) 41(7):1099-1102.
47. Smith KL, Tao ZF, Hashimoto S, Leitheiser CJ, Wu X, Hecht SM: Deglycobleomycin: Solid-phase synthesis and DNA cleavage by the resin-bound ligand. Org Lett (2002) 4(7):1079-1082. Solid-phase synthesis of deglycobleomycin using Dde linker.
48. Tao ZF, Leitheiser CJ, Smith KL, Hashimoto S, Hecht SM: Solid-phase synthesis of deglycobleomycins: A C-terminal tetraamine linker that permits direct evaluation of resin-bound bleomycins. Bioconjug Chem (2002) 13(3):426-434. Evaluation of bead-bound deglycobleomycins following solid-phase synthesis.
49. Umezawa H: Natural and artificial bleomycins: Chemistry and antitumor activities. Pure Appl Chem (1971) 28(4):665-680.
50. Quada JC Jr, Zuber GF, Hecht SM: Interaction of bleomycin with DNA. Pure Appl Chem (1998) 70(2):307-312.
51. Thomas CJ, McCormick MM, Vialas C, Tao ZF, Leitheiser CJ, Rishel MJ, Wu X, Hecht SM: Alteration of the selectivity of DNA cleavage by a deglycobleomycin analogue containing a trithiazole moiety. J Am Chem Soc (2002) 124(15):3875-3884.
52. Carter BJ, Murty VS, Reddy KS, Wang SN, Hecht SM: A role for the metal binding domain in determining the DNA sequence selectivity of Fe-bleomycin. J Biol Chem (1990) 265(8):4193-4196.
53. Carter BJ, Reddy KS, Hecht SM: Polynucleotide recognition and strand scission by Fe-bleomycin. Tetrahedron (1991) 47(14-15):2463-2474.
54. 2 L-threonine side chain: Its role in preorganization of a compact conformation implicated in sequence-selective DNA cleavage. J Am Chem Soc (1998) 120(36):9139-9148.
55. 2 valerate substituents: Preorganization of a rigid, compact conformation implicated in sequence-selective DNA cleavage. J Am Chem Soc (1998) 120(36):9149-9158.
56. Iitaka Y, Nakamura H, Nakatani T, Muraoka Y, Fujii A, Takita T, Umezawa H: Chemistry of bleomycin. XX. The X-ray structure determination of P-3A Cu(II)-complex, a biosynthetic intermediate of bleomycin. J Antibiot (1978) 31(10):1070-1072.
57. 2: Functional characterization of imidazole N metal complexation. Bioorg Med Chem (1996) 4(2):195-207.
58. Leitheiser CJ, Smith KL, Rishel MJ, Hashimoto S, Konishi K, Thomas CJ, Li C, McCormick MM, Hecht SM: Solid-phase synthesis of bleomycin group antibiotics. Construction of a 108-member deglycobleomycin library. J Am Chem Soc (2003) 125(27):8218-8227. This paper represents the first report of a bleomycin combinatorial library.
59. Oppenheimer NJ, Rodriguez LO, Hecht SM: Structural studies of 'active complex' of bleomycin: Assignment of ligands to the ferrous ion in a ferrous-bleomycin-carbon monoxide complex. Proc Natl Acad Sci USA (1979) 76(11):5616-5620.
60. 2-iron(II)-carbon monoxide complex by means of two-dimensional NMR spectroscopy and distance geometry calculations. J Am Chem Soc (1990) 112(21):7462-7474.
61. 5 glycoconjugate. Org Lett (2001) 3(9):1291-1294.
62. 2. J Am Chem Soc (1995) 117(28):7344-7356.
63. Thomas CJ, Chizhov AO, Leitheiser CJ, Rishel MJ, Konishi K, Tao ZF, Hecht SM: Solid-phase synthesis of bleomycin A5 and three monosaccharide analogues: Exploring the role of the carbohydrate moiety in RNA cleavage. J Am Chem Soc (2002) 124(44):12926-12927. Synthesis of bleomycin and glycosylated analogs on a solid support.
64. Phe mediated by metal-free bleomycin. Biochemistry (1995) 34(37):12029-12037.