Development of distamycin-related DNA binding anticancer drugs

Expert Opinion on Investigational Drugs

Volumn 10, Issue 9, 2001, Pages 1703-1714

  Marchini, S ^a   Broggini, M ^a   Sessa, C ^a   D'Incalci, M ^a  

^a Ist Ricerche Farmacol Mario Negri ^*  (Italy)

Author keywords

Alkylating agents; DNA sequence specificity; Glutathione; Minor groove binders

Indexed keywords

ADENINE; ADOZELESIN; ALKYLATING AGENT; ALPHA BROMOACRYLAMIDO TETRAPYRROLECARBAMOYL DERIVATIVE; ALPHA BROMOACRYLOYL DISTAMYCIN DERIVATIVE; ANTHRAMYCIN; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BIZELESIN; BROSTALLICIN; CARZELESIN; CISPLATIN; CONGOCIDINE; CYTOSINE; DISTAMYCIN A; DISTAMYCIN A DERIVATIVE; DNA; GUANINE; MINOR GROOVE BINDERS; MITOMYCIN C; PLATINUM DERIVATIVE; PNU 151807; RACHELMYCIN; RACHELMYCIN DERIVATIVE; TALLIMUSTINE; THYMINE; TRABECTEDIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; BONE MARROW CELL; BONE MARROW TOXICITY; CLINICAL TRIAL; COLORECTAL CANCER; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DNA REPAIR; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DNA BINDING; DRUG MECHANISM; DRUG RESISTANCE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; GROWTH INHIBITION; HUMAN; MOUSE; NAUSEA AND VOMITING; NEUTROPENIA; NONHUMAN; OVARY CARCINOMA; PHASE 1 CLINICAL TRIAL; PHASE 2 CLINICAL TRIAL; REVIEW; SEQUENCE ANALYSIS; SMALL CELL CARCINOMA; THROMBOCYTOPENIA; TISSUE NECROSIS; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BINDING SITES; DISTAMYCINS; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS;

EID: 0034850672     PISSN: 13543784     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543784.10.9.1703     Document Type: Review

References (76)

1. DNA as a target for drug action
2. Covalent modification of DNA by antineoplastic agents
3. Structural studies of atom-specific anticancer drugs acting on DNA
4. DNA crosslinking and cytotoxicity in normal and transformed human cells treated with antitumor nitrosoureas
5. DNA crosslinking and monoadduct repair in nitrosourea-treated human tumour cells
6. The cytotoxicity, DNA crosslinking ability and DNA sequence selectivity of the aniline mustards melphalan, chlorambucil and 4-[bis(2-chloroethyl)amino] benzoic acid
7. Effect of ionic strength and cationic DNA affinity binders on the DNA sequence selective alkylation of guanine N7-positions by nitrogen mustards
8. GC-rich regions in genomes as targets for DNA alkylation
9. Molecular electrostatic potential of the nucleic acids
10. DNA cross-linking and sequence selectivity of aziridinylbenzoquinones: A unique reaction at 5′-GC-3′ sequences with 2,5-diaziridinyl-1,4-benzoquinone upon reduction
11. DNA sequence recognition altered bis-benzimidazole minor groove binders
12. Design, synthesis, and biological evaluation of DNA sequence and minor groove selective alkylating agents
13. Synthetic DNA minor groove-binding drugs
14. DNA-minor-groove alkylators, a new class of anticancer agents
15. DNA minor groove binding ligands: A new class of anticancer agents
16. Phase I clinical and pharmacokinetic study of carzelesin (U-80244) given daily for five consecutive days
17. Phase I study of adozelesin administered by 24-hour continuous intravenous infusion
18. Myelotoxic effects of the bifunctional alkylating agent bizelesin on human, canine and murine myeloid progenitor cells
19. Phase I trial of bizelesin using a single bolus infusion given every 28 days in patients with advanced cancer
20. DNA sequence- and structure-selective alkylation of guanine N2 in the DNA minor groove by ecteinascidin 743, a potent antitumor compound from the Caribbean tunicate Ecteinascidia turbinata
21. Unique pattern of ET-743 activity in different cellular systems with defined deficiencies in DNA-repair pathways
22. Ecteinascidin-743 (ET-743), a natural marine compound, with a unique mechanism of action
23. DNA minor groove-binding ligands: A different class of mammalian DNA topoisomerase I inhibitors
24. Distamycin-induced inhibition of homeodomain-DNA complexes
25. Distamycins inhibit the binding of OTF-1 and NFE-1 transfactors to their conserved DNA elements
26. DNA recognition by lexitropsins, minor groove binding agents
27. Molecular recognition between oligopeptides and nucleic acids: Novel imidazole-containing oligopeptides related to netropsin that exhibit altered DNA sequence specificity
28. Lexitropsins: Design and development of sequence selective DNA minor groove binding agents as news chemotherapeutics
29. Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues
30. Experimental studies of distamycin A. A new antibiotic with cytotoxic activity
31. Map of distamycin, netropsin and actinomycin binding sites on heterogeneous DNA: DNA cleavage inhibition with methidium propyl-EDTA-Fe(II)
32. Sequence specificity of alkylation for a series of nitrogen mustard-containing analogues of distamycin of increasing binding site size: Evidence for increased cytotoxicity with enhanced sequence specificity
33. Sequence-specific cleavage of DNA by N-bromoacetyldistamycin. Product and kinetic analyses
34. Groove- and sequence-selective alkylation of DNA by sulfonate esters tethered to lexitropsins
35. [2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid inhibits DNA binding to transcription factor Sp 1
36. Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c] [1,4]benzodiazepine and minor-groove-binding oligopyrrole carriers
37. Design, synthesis and biological activity of a pyrrolo [2,1-c] [1,4]benzodiazepine (PBD)-distamycin hybrid
38. Design, synthesis, cytotoxic properties and preliminary DNA sequencing evaluation of CPI-N-methylpyrrole hybrids. Enhancing effect of a trans double bond linker and role of the terminal amide functionality on cytotoxic potency
39. Synthesis, DNA-binding properties, and antitumor activity of novel distamycin derivatives
40. In vivo antitumor activity of FCE 24517, a novel Distamycin A derivative with specificity for A-T rich sequences of DNA
41. Biological profile of FCE 24517, a novel benzoyl mustard analogue of distamycin A
42. Distamycin derivative in vitro and in vivo activity of a new class of antitumor agents
43. Establishment of L1210 leukemia cells resistant to the distamycin-A derivative (FCE 24517): Characterization and cross-resistance studies
44. Selective DNA interaction of the novel distamycin derivative FCE 24517
45. The effects of a benzoic acid mustard derivative of distamycin A (FCE 24517) and related minor groove-binding distamycin analogues on the activity of major groove-binding alkylating agents
46. Characterisation of a LoVo subline resistant to a benzoyl mustard derivative of distamycin A (FCE 24517)
47. Decreased tyrosine phosphorylation in tumour cells resistant to FCE 24517 (tallimustine)
48. The alkylating antitumor drug tallimustine does not induce DNA repair
49. 3-methyladenine-DNA-glycosylase and O6-alkyl guanine-DNA-alkyltransferase activities and sensitivity to alkylating agents in human cancer cell lines
50. Mismatch repair deficiency is associated with resistance to DNA minor groove alkylating agents
51. DNA sequence-specific adenine alkylation by the novel antitumor drug tallumustine (FCE 24517), a benzoyl nitrogen mustard derivative of distamycin
52. DNA adduct formation of the sequence selective cytotoxic agent tallimustine resolved at the nucleotide level in a single copy gene in mammalian cells
53. Sequence-specific DNA alkylation of novel tallimustine derivatives
54. Phase I study of the novel distamycin derivative tallimustine (FCE 24517)
55. Distamycin A derivative, FCE 24517: A Phase I study in solid tumors
56. A Phase I and pharmacokinetic study of tallimustine [PNU 152241 (FCE 24517)] in patients with advanced cancer
57. Tallimustine in advanced previously untreated colorectal cancer, a Phase II study
58. Tallimustine is inactive in patients with previously treated small cell lung cancer
59. Tallimustine, an effective antileukemic agent in a severe combined immunodeficient mouse model of adult myelogenous leukemia, induces remissions in a Phase I study
60. Novel benzoyl nitrogen mustard derivatives of pyrazole analogues of distamycin A: Synthesis and antileukemic activity
61. Synthesis, DNA binding, cytotoxicity and sequence specificity of a series of imidazole-containing analogs of the benzoic acid mustard distamycin derivative tallimustine containing an alkylating group at the C-terminus
62. A new class of cytotoxic DNA minor groove binders: Alpha-Halogenoacrylic derivatives of pyrrolecarbamoyl oligomers
63. Phenyl sulfur mustard derivatives of distamycin A
64. Synthesis and antitumor activity of new benzoheterocyclic derivatives of distamycin A
65. DNA sequence-recognizing properties of minor groove alkylating agents. Effects of the replacement of N-methylpyrrole by an N-methylimidazole on tallimustine and its own homologue
66. Recent outcome in the field of distamycin-derived minor groove binders
67. Cytotoxics derived from distamycin A and congeners
68. Cytotoxic halogenoacrylic derivatives of distamycin A
69. p53-independent caspase-mediated apoptosis in human leukaemic cells is induced by a DNA minor groove binder with antineoplastic activity
70. Alpha-bromoacryloyl derivative of distamycin A (PNU 151807): A new non-covalent minor groove DNA binder with antineoplastic activity
71. Cytotoxic alpha-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety
72. Antitumor activity of PNU-166196, a novel DNA minor groove binder selected for clinical development
73. Phase I study of PNU-166196, a novel DNA minor groove binder (MGB) with enhanced activity in tumor models expressing high Glutathione (GSH) levels, administered to patients (Pts) with advanced cancer
74. Phase I study of PNU-166196 given on a weekly basis
75. Structural studies of atom-specific anticancer drugs acting on DNA
76. Crystal structure of a covalent DNA-drug adduct: Anthramycin bound to C-C-A-A-C-G-T-T-G-G and a molecular explanation of specificity