Synthesis of new homochiral bispyrrolidines as potential DNA cross-linking antitumour agents

Anti-Cancer Drug Design

Volumn 15, Issue 2, 2000, Pages 119-126

  Anderson, Fiona M ^a   O'Hare, C Caroline ^b   Hartley, John A ^b   Robins, David J ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Alkylating agent; Bispyrrolidine; DNA cross linking

Indexed keywords

ALKYLATING AGENT; ANTINEOPLASTIC AGENT; AZIRIDINE; CARBON; DNA; NITROGEN; PIPERAZINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CANCER CELL; CONTROLLED STUDY; DNA CROSS LINKING; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMINES; ANTINEOPLASTIC AGENTS; CELL SURVIVAL; CROSS-LINKING REAGENTS; DNA; DRUG DESIGN; HUMANS; INDICATORS AND REAGENTS; K562 CELLS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

BRASSICACEAE;

EID: 0034051360     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Bedford P., Fox B.W. (1983) DNA-DNA interstrand cross-linking by dimethanesulphonic acid esters. Biochemical Pharmacology, 32, 2297.
2. Chabner B.A., Longo D.L. (eds) (1996) Cancer Chemotherapy and Biotherapy: Principles and Practice. Lippincott-Raven: Philadelphia, PA.
3. Hartley J.A. (1993) Selectivity in alkylating agent-DNA interactions. In Molecular Aspects of Anticancer Drug-DNA Interactions. Neidle S., Waring M.J. (eds), p. 1. Macmillan Press: Basingstoke.
4. Hartley J.A., Berardini M.D., Souhami R.L. (1991) An agarose gel method for the determination of DNA interstrand crosslinking applicable to the measurement of the rate of total and 'second-arm' cross-link reactions. Analytical Biochemistry, 193, 131.
5. Henderson N.D., Plumb J.A., Robins D.J., Workman P. (1996) Synthesis and anti-cancer activity of 2,6-disubstituted N-methylpiperidine derivatives and their N-oxides. Anti-Cancer Drug Design, 11, 421.
6. Henderson N.D., Lacy S.M., O'Hare C.C., Hartley J.A., McClean S., Wakelin L.P.G., Kelland L.R., Robins D.J. (1998) Synthesis of new bifunctional compounds which selectively alkylate guanines in DNA. Anti-Cancer Drug Design, 13, 749.
7. Kohn K.W., Hartley J.A., Mattes W.B. (1987) Mechanisms of DNA-sequence selective alkylation of guanine-N7 position by nitrogen mustards. Nucleic Acids Research, 15, 10531.
8. Lee M., Rhodes A.L., Wyatt M.D., Forrow S., Hartley J.A. (1993) Design, synthesis and biological evaluation of DNA sequence and minor groove selective alkylating agents. Anti-Cancer Drug Design, 8, 173.
9. Madeyski C.M., Michael J.P., Hancock R.D. (1984) N,N′,N″,N‴-Tetrakis(2-hydroxyethyl)cyclam, an N-donor macrocycle with rapid metalation reactions. Inorganic Chemistry, 23, 1487.
10. Mattes W.B., Hartley J.A., Kohn K.W. (1986) DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards. Nucleic Acids Research, 14, 2971.
11. McHugh P.J., Gill R.D., Waters R., Hartley J.A. (1999) Excision repair of nitrogen mustard-DNA adducts in Saccharomyces cerevisiae. Nucleic Acids Research, 27, 3259.
12. Mosmann T. (1983) Rapid colorimetric assay for cellular growth and survival: application of proliferation and cytotoxicity assay. Journal of Immunological Methods, 65, 55.
13. Ponti M., Souhami R.L., Fox B.W., Hartley J.A. (1991) DNA interstrand cross-linking and sequence selectivity of dimethanesulphonates. British Journal of Cancer, 63, 743.
14. Sunters A., Springer C.J., Bagshawe K., Souhami R.L., Hartley J.A. (1992) The cytotoxicity, DNA cross-linking ability and DNA sequence selectivity of the aniline mustards melphalan, chlorambucil and 4-[bis(2-chloroethyl)amino]benzoic acid. Biochemical Pharmacology, 44, 59.
15. Zadel G., Breitmaier E. (1994) (5AS, 10AS)-Octahydro-1H,5H-dipyrrolo[1,2-a-1′,2″-d]pyrazine DPP as auxiliary reagent for enantioselective alkylations of prochiral carbonyl-compounds. Chemische Berichte, 127, 1323.