Development of distamycin-related DNA binding anticancer drugs

REFERENCES

• HURLEY LH, BOYD FL: DNA as a target for drug action. Trends Pharmacol. Li. (1988) 9:402–407.
   PubMed Web of Science ®Google Scholar
• ••This paper provides a structural explanation for the DNA sequence specificity of CC-1065-induced adducts. The paper is the basis for the development of this class of compounds as potentially novel compounds possessing an original mode of action.
   Google Scholar
• HEMMINKI K, LUDLUM DB: Covalentmodification of DNA by antineoplastic agents. J Nati Cancer Inst. (1984) 73:1021–1028.
   PubMed Web of Science ®Google Scholar
• YANG XL, WANG AH: Structural studiesof atom-specific anticancer drugs acting on DNA. Pharmacol. Therapeut. (1999) 83:181–215.
   PubMed Web of Science ®Google Scholar
• ERICKSON LC, BRADLEY MO, DUCORE JM, EWIG RA, KOHN KW: DNA crosslinking and cytotoxicity in normal and transformed human cells treated with antitumor nitrosoureas. Proc. Nati Acad. Sri. USA (1980) 77:467–471.
   PubMed Web of Science ®Google Scholar
• ERICKSON LC, LAURENT G, SHARKEY NA, KOHN KW: DNA cross-linking and monoadduct repair in nitrosourea-treated human tumour cells. Nature (1980) 288:727–729.
   PubMed Web of Science ®Google Scholar
• SUNTERS A, SPRINGER CJ, BAGSHAWE KD, SOUHAMI RL, HARTLEY JA: The cytotoxicity, DNA crosslinking ability and DNA sequence selectivity of the aniline mustards melphalan, chlorambucil and 4- lbis(2-chloroethyOaminolbenzoic acid. Biochem. Pharmacol. (1992) 44:59–64.
   PubMed Web of Science ®Google Scholar
• HARTLEY JA, FORROW SM, SOUHAMIRL: Effect of ionic strength and cationic DNA affinity binders on the DNA sequence selective alkylation of guanine N7-positions by nitrogen mustards. Biochemistry (1990) 29:2985–2991.
   PubMed Web of Science ®Google Scholar
• MATTES WB, HARTLEY JA, KOHN KW, MATHESON DW: GC-rich regions in genomes as targets for DNA alkylation. Carcirrogerresis (1988) 9:2065–2072.
   PubMed Web of Science ®Google Scholar
• PULLMAN A, PULLMAN B: Molecular electrostatic potential of the nucleic acids. Q. Rev. Biophys. (1981) 14:289–380.
   PubMed Web of Science ®Google Scholar
• HARTLEY JA, BERARDINI M, PONTI M et al.: DNA cross-linking and sequence selectivity of aziridinylbenzoquinones: a unique reaction at 5'-GC-3' sequences with 2,5-diaziridiny1-1,4-benzoquinone upon reduction. Biochemistry (1991) 30: 11719-11724.
   Google Scholar
• LOWN JW: DNA sequence recognition altered bis-benzimidazole minor groove binders. In: Advances in DNA Sequence Specific Agents. Graham BJ (Ed.), (vol. 3) JAI Press, Greenwich (1997):67–95.
   Google Scholar
• LEE M, RHODES AL, WYATT MD, FORROW S, HARTLEY JA: Design, synthesis, and biological evaluation of DNA sequence and minor groove selective alkylating agents. Anti-Cancer Drug Des. (1993) 8:173–192.
   PubMedGoogle Scholar
• ••The paper shows that the sequence specificity of alkylation is an important feature of minor groove binders possessing antitumour activity. The comparison of the biological activity of different analogues shows that the number of DNA lesions is a much less relevant factor than the sequence specificity of alkylations.
   Google Scholar
• REDDY BS, SONDHI SM, LOWN JW:Synthetic DNA minor groove-binding drugs. Pharmacol. Therapeut. (1999) 84:1–111.
   PubMed Web of Science ®Google Scholar
• D'INCALCI M: DNA-minor-groove alkylators, a new class of anticancer agents. Ann. Oncol. (1994) 5:877–878.
   Google Scholar
• D'INCALCI M, SESSA C: DNA minor groove binding ligands: A new class of anticancer agents. Expert Opin. Investig. Drugs (1997) 6:875–884.
   PubMedGoogle Scholar
• WOLFF I, BENCH K, BEIJNEN JH etal.: Phase I clinical and pharmacokinetic study of carzelesin (U-80244) given daily for five consecutive days. Clin. Cancer Res. (1996) 2:1717–1723.
   Google Scholar
• FLEMING GF, RATAIN MJ, O'BRIEN SM et al.: Phase I study of adozelesin administered by 24-hour continuous intravenous infusion. j Nati Cancer Inst. (1994)86:368–372.
   Google Scholar
• VOLPE DA, TOMASZEWSKI JE, PARCHMENT RE etal.: Myelotoxic effects of the bifunctional alkylating agent bizelesin on human, canine and murine myeloid progenitor cells. Cancer Chemother. Pharmacol. (1996) 39:143–149.
   Google Scholar
• SCHWARTZ GH, AYLESWORTH C, STEPHENSON J et al.: Phase I trial of bizelesin using a single bolus infusion given every 28 days in patients with advanced cancer. Proc. Am. Soc. Clin. Oncol. (2000) 19:235a.
   Google Scholar
• POMMIER Y, KOHLHAGEN G, BAILEY C, WARING M, MAZUMDER A, KOHN KW: 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. Biochemistry (1996) 35:13303–13309.
   PubMed Web of Science ®Google Scholar
• DAMIA G, SILVESTRI S, CARRASSA L et al.: Unique pattern of ET-743 activity in different cellular systems with defined deficiencies in DNA-repair pathways. Int. J. Cancer (2001) 92:583–588.
   PubMed Web of Science ®Google Scholar
• ERBA E, BERGAMASCHI D, BASSANO L et al.: Ecteinascidin-743 (ET-743), a natural marine compound, with a unique mechanism of action. Eur. J. Cancer (2001) 37:97–105.
   PubMed Web of Science ®Google Scholar
• •This paper describes the biological activity and the mechanism of action of the DNA minor groove binder ET-743, showing that it differs from both the conventional alkylating agents and previously identified minor groove antitumor drugs such as distamycin.
   Google Scholar
• CHEN AY, YU C, GATTO B, LIU LF: DNA minor groove-binding ligands: a different class of mammalian DNA topoisomerase I inhibitors. Proc. Nati Acad. Sci. USA (1993) 90:8131–8135.
   PubMed Web of Science ®Google Scholar
• DORN A, AFFOLTER M, MULLER M, GEHRING WJ, LEUPIN W: Distamycin-induced inhibition of homeodomain-DNA complexes. EMBO J. (1992) 11:279–286.
   PubMed Web of Science ®Google Scholar
• BROGGINI M, PONTI M, OTTOLENGHI S, D'INCALCI M, MONGELLI N, MANTOVANI R: Distamycins inhibit the binding of OTF-1 and NFE-1 transfactors to their conserved DNA elements. Nucleic Acids Res. (1989) 17:1051–1059.
   PubMed Web of Science ®Google Scholar
• ••This is the first paper that shows that it ispossible to modify transcription regulation by the use of compounds which change the structure of specific DNA sequences which are the binding sites for transcription factor.
   Google Scholar
• LOWN JW: DNA recognition by lexitropsins, minor groove binding agents. J. Mole. Recognit. (1994) 7:79–88.
   PubMedGoogle Scholar
• LOWN JW, KROWICKI K, BHAT UG, SKOROBOGATY A, WARD B, DABROWIAK JC: Molecular recognition between oligopeptides and nucleic acids: novel imidazole-containing oligopeptides related to netropsin that exhibit altered DNA sequence specificity. Biochemistry (1986) 25:7408–7416.
   PubMed Web of Science ®Google Scholar
• SINGH MP, LOWN JW: Lexitropsins: design and development of sequence selective DNA minor groove binding agents as news chemotherapeutics. In: Progress in Medicinal Chemistry Choudhary MI (Ed.), Harwood Academic Publishers, Amsterdam (1996):49–171.
   Google Scholar
• BAILEY C, CHAIRES JB: Sequence-specific DNA minor groove binders. Design and synthesis of netropsin and distamycin analogues. Biocohjugate Chem. (1998) 9:513–538.
   Google Scholar
• DI MARCO A, GAETANI M, OREZZI E SCOTTI T, ARCAMONE F: Experimental studies of distamycin A. A new antibiotic with cytotoxic activity. Cancer Chemother. Rep. (1962) 18:15–19.
   Google Scholar
• VAN DYKE MW, HERTZBERG RE DERVAN PB: Map of distamycin, netropsin and actinomycin binding sites on heterogeneous DNA: DNA cleavage inhibition with methidium propyl-EDTA-Fe(II). Proc. Natl. Acad. Sci. USA (1982) 79:5470–5474.
   PubMed Web of Science ®Google Scholar
• WYATT MD, LEE M, GARBIRAS BJ, SOUHAMI RL, HARTLEY JA: 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. Biochemistry (1995) 34:13034–13041.
   PubMed Web of Science ®Google Scholar
• BAKER BE DERVAN PB: Sequence-specific cleavage of DNA by N-bromoacetyldistamycin. Product and kinetic analyses. J. Am. Chem. Soc. (1989) 111:2700–2712.
   Web of Science ®Google Scholar
• ZHANG Y, CHEN FX, MEHTAP, GOLD B: Groove- and sequence-selective alkylation of DNA by sulfonate esters tethered to lexitropsins. Biochemistry (1993) 32:7954–7965.
   PubMed Web of Science ®Google Scholar
• BARALDI PG, CACCIARI B, GUIOTTO A et al.: [2,1-c1[1,41benzodiazepine (PBD)-distamycin hybrid inhibits DNA binding to transcription factor Sp I. Nucleo. Nucleo. Nucleic Acids (2000) 19:1219–1229.
   PubMed Web of Science ®Google Scholar
• BARALDI PG, BALBONI G, CACCIARI B et al.: Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo [2,1-cl [1, 41benzodiazepine and minor-groove-binding oligopyrrole carriers. J. Med. Chem. (1999) 42:5131–5141.
   PubMed Web of Science ®Google Scholar
• BARALDI PG, CACCIARI B, GUIOTTO A et al.: Design, synthesis and biological activity of a pyrrolo [2,1- c][1, 41benzodiazepine (PBD)-distamycin hybrid. Bioorg. Med. Chem. Lett. (1998) 8:3019–3024.
   PubMed Web of Science ®Google Scholar
• WANG Y, GUPTA R, HUANG L, LUO W, LOWN JW: 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. Anti-Cancer Drug Des. (1996) 11:15–34.
   Google Scholar
• ••This paper shows that tallimustinealkylates DNA in a sequence-specific manner and defines its biological properties: the paper demonstrates that tallimustine is mechanistically and biologically different from other nitrogen mustards which alkylates DNA in the major groove.
   Google Scholar
• ARCAMONE FM, ANIMATI BARBIERI B et al.: Synthesis, DNA-binding properties, and antitumor activity of novel distamycin derivatives. J. Med. Chem. (1989) 32:774–778.
   Google Scholar
• BARBIERI B, GIULIANI FC, PEZZONI G, LAZZARI E, ARCAMONE F, MONGELLI N: In vivo antitumor activity of FCE 24517, a novel Distamycin A derivative with specificity for A-T rich sequences of DNA. Proc. Am. Assoc. Cancer Res. (1988) 29:330.
   Web of Science ®Google Scholar
• PEZZONI G, GRANDI M, BIASOLI G et al.: Biological profile of FCE 24517, a novel benzoyl mustard analogue of distamycin A. Br. J. Cancer (1991) 64:1047–1050.
   PubMed Web of Science ®Google Scholar
• GIULIANI FC, BARBIERI B, BIASOLI L, GERONI C, MENOZZI M and MONGELLI N: Distamycin derivative in vitro and in vivo activity of a new class of antitumor agents. Proc. Am. Assoc. Cancer Res. (1988) 29:330.
   Google Scholar
• GERONI C, PESENTI E, TAGLIABUE G et al.: Establishment of L1210 leukemia cells resistant to the distamycin-A derivative (FCE 24517): characterization and cross-resistance studies. Int. J. Cancer (1993) 53:308–314.
   PubMed Web of Science ®Google Scholar
• BROGGINI M, ERBA E, PONTI M et al.:Selective DNA interaction of the novel distamycin derivative FCE 24517. Cancer Res. (1991) 51:199–204.
   PubMed Web of Science ®Google Scholar
• COLEY HM, MONGELLI N, D'INCALCI M: 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. Biochem. Pharmacol. (1993) 45:626.
   Google Scholar
• CAPOLONGO L, MELEGARO G, BROGGINI M, MONGELLI N, GRANDI M: Characterisation of a LoVo subline resistant to a benzoyl mustard derivative of distamycin A (FCE 24517). Br J. Cancer (1993) 68:916–919.
   PubMed Web of Science ®Google Scholar
• CIOMEI M, PASTORI W, CAPOLONGO L et al.: Decreased tyrosine phosphorylation in tumour cells resistant to FCE 24517 (tallimustine). Br. J. Cancer (1995) 72:1504–1508.
   PubMed Web of Science ®Google Scholar
• ROSSI R, MONTECUCCO A, CAPOLONGO L et al.: The alkylating antitumor drug tallimustine does not induce DNA repair. Anti-Cancer Res. (1996) 16:3779–3783.
   PubMed Web of Science ®Google Scholar
• DAMIA G, IMPERATORI L, CITTI L, MARIANI L and D'INCALCI M: 3-methyladenine-DNA-glycosylase and 06-alkyl guanine-DNA-alkyltransferase activities and sensitivity to alkylating agents in human cancer cell lines. Br J. Cancer (1996) 73:861–865.
   PubMed Web of Science ®Google Scholar
• COLELLA G, MARCHINI S, D'INCALCI M, BROWN R, BROGGINI M: Mismatch repair deficiency is associated with resistance to DNA minor groove alkylating agents. Br J. Cancer (1999) 80:338–343.
   PubMed Web of Science ®Google Scholar
• •The paper shows that mismatch-deficient cells can be less sensitive to minor groove binders such as talllimustine or CC-1065. This difference was previously demonstrated for cisplatin but not for other alkylating agents.
   Google Scholar
• BROGGINI M, COLEY HM, MONGELLI N et al.: DNA sequence-specific adenine alkylation by the novel antitumor drug tallumustine (FCE 24517), a benzoyl nitrogen mustard derivative of distamycin. Nucleic Acids Res. (1995) 23:81–87.
   PubMed Web of Science ®Google Scholar
• ••The unique DNA alkylation site oftallimustine has been defined. The recognition of a specific hexamer has been interpreted and explained.
   Google Scholar
• BECCAGLIA P, GRIMALDI KA, HARTLEY JA, MARCHINI S, BROGGINI M, D'INCALCI M: DNA adduct formation of the sequence selective cytotoxic agent tallimustine resolved at the nucleotide level in a single copy gene in mammalian cells. Br. J.Cancer (1996) 73 (Suppl.XXVI):12.
   Google Scholar
• MARCHINI S, COZZI P, BERIA I etal.: Sequence-specific DNA alkylation of novel tallimustine derivatives. Anti-Cancer Drug Des. (1998) 13:193–205.
   Google Scholar
• SESSA C, PAGANI 0, ZURLO MG et al.: Phase I study of the novel distamycin derivative tallimustine (FCE 24517). ArimOricoL (1994) 5:901–907.
   Google Scholar
• ABIGERGES D, ARMAND JP, DA COSTA L: Distamycin A derivative, FCE 24517: a Phase I study in solid tumors. Proc. Am. Assoc. Cancer Res. (1993) 34:267.
   Google Scholar
• •The first Phase I trial of the distamycin derivative, tallimustine is reported in these two papers. The unexpected bone marrow toxicity has been investigated in patients receiving the treatment.
   Google Scholar
• WEISS GR, POGGESI I, ROCCHETTI M et al.: A Phase land pharmacokinetic study of tallimustine FPNU 152241 (FCE 24517)] in patients with advanced cancer. Chu. Cancer Res. (1998) 4:53–59.
   PubMed Web of Science ®Google Scholar
• PUNT CJ, HUMBLET Y, ROCA E et al.: Tallimustine in advanced previously untreated colorectal cancer, a Phase II study. Br. J. Cancer (1996) 73:803–804.
   PubMed Web of Science ®Google Scholar
• VIALLET J, STEWART D, SHEPHERD F et al.: Tallimustine is inactive in patients with previously treated small cell lung cancer. A Phase II trial of the National Cancer Institute of Canada Clinical Trials Group. Lung Cancer (1996) 15:367–373.
   Google Scholar
• BERAN M, JEHA S, O'BRIEN S et al.: Tallimustine, an effective antileukemic agent in a severe combined immunodeficient mouse model of adult myelogenous leukemia, induces remissions in a Phase I study. Clin. Cancer Res. (1997) 3:2377–2384.
   Google Scholar
• BARALDI PG, COZZI P, GERONI C, MONGELLI N, ROMAGNOLI Rand SPALLUTO G: Novel benzoyl nitrogen mustard derivatives of pyrazole analogues of distamycin A: synthesis and antileukemic activity. Bioorgarr. Med. Chem. (1999) 7:251–262.
   PubMed Web of Science ®Google Scholar
• BROOKS N, LEE M, WRIGHT SR, WOO S, CENTIONI S and HARTLEY JA: 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. Anti-Cancer Drug Dec. (1997) 12:591–606.
   PubMed Web of Science ®Google Scholar
• COZZI P: A new class of cytotoxic DNAminor groove binders: alpha-Halogenoacrylic derivatives of pyrrolecarbamoyl oligomers. Farmaco (2001) 56:57–65.
   PubMedGoogle Scholar
• COZZI P, BERIA I, CALDARELLI M et al.: Phenyl sulfur mustard derivatives of distamycin A. Bioorg. Medd Chem. Lett. (2000) 10:1653–1656.
   PubMed Web of Science ®Google Scholar
• BARALDI PG, ROMAGNOLI R, BERIA I etal.: Synthesis and antitumor activity of new benzoheterocyclic derivatives of distamycin A. J. Med. Chem. (2000) 43:2675–2684.
   Google Scholar
• BARALDI PG, ROMAGNOLI R, SPALLUTO G et al.: 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. Arzneimittel-Forsch. (2000) 50:309–315.
   Google Scholar
• COZZI P: Recent outcome in the field of distamycin-derived minor groove binders. Farmaco (2000) 55:168–173.
   PubMedGoogle Scholar
• COZZI P, MONGELLI N: Cytotoxics derived from distamycin A and congeners. Cum: Pharm. Design (1998) 4:181–201.
   PubMed Web of Science ®Google Scholar
• COZZI P, BERIA I, CALDARELLI M, CAPOLONGO L, GERONI C, MONGELLI N: Cytotoxic halogenoacrylic derivatives of distamycin A. Bioorg. Med. Chem. Lett. (2000) 10:1269–1272.
   PubMed Web of Science ®Google Scholar
• MARCHINI S, CIRO M and BROGGINI M: p53-independent caspase-mediated apoptosis in human leukaemic cells is induced by a DNA minor groove binder with antineoplastic activity. Apoptosis (1999) 4:39–45.
   PubMed Web of Science ®Google Scholar
• MARCHINI S, CIRO M, GALLINARI F etal.: Alpha-bromoacryloyl derivative of distamycin A (PNU 151807): a new non-covalent minor groove DNA binder with antineoplastic activity. Br J. Cancer (1999) 80:991–997.
   Google Scholar
• COZZI P, BERIA I, CALDARELLI M, GERONI C, MONGELLI N and PENNELLA G: Cytotoxic alpha-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety. Bioorg. Med. Chemi. Lett. (2000) 10:1273–1276.
   PubMed Web of Science ®Google Scholar
• GERONI C, PENNELLA G, CAPOLONGO L et al.: Antitumor activity of PNU-166196, a novel DNA minor groove binder selected for clinical development. Proc. Am. Assoc. Cancer Res. (2000) 41:265.
   Google Scholar
• PLANTING AS, DE JONGE MJA, VAN DER GAAST A et al.: Phase I study of PNU-166196, a novel DNA minor groove binder (MGM with enhanced activity in tumor models expressing high Glutathione (GSH levels, administered to patients (Pts)with advanced cancer. Proc. Am. Soc. Chh. Oricol (2001) 20:96a.
   Google Scholar
• HANDE KR, ROTH BJ, VREELAND F et al.: Phase I study of PNU-166196 given on a weekly basis. Proc. Am. Soc. CM]. Oricol (2001) 20:96a.
   Google Scholar
• YANG XL, WANG AH: Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Therapeut. (1999) 83:181–215.
   PubMed Web of Science ®Google Scholar
• KOPKA ML, GOODSELL DS, BAIKALOV I, GRZESKOWIAK K, CASCIO D, DICKERSON RE: Crystal structure of a covalent DNA-drug adduct: anthramycin bound toCCAACGTT G-G and a molecular explanation of specificity. Biochemistry (1994) 33:13593–13610.
   PubMed Web of Science ®Google Scholar