Design and optimization of 20-O-linked camptothecin glycoconjugates as anticancer agents

Journal of Medicinal Chemistry

Volumn 44, Issue 24, 2001, Pages 4186-4195

  Lerchen, H G ^a   Baumgarten, J ^a   Von dem Bruch, K ^a   Lehmann, T E ^a   Sperzel, M ^a   Kempka, G ^a   Fiebig, H H ^b  

^a BAYER AG   (Germany)

^b CHARLES RIVER LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]ARGINYL DEXTRO VALYL]CAMPTOTHECIN; 20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]ARGINYLVALYL]CAMPTOTHECIN; 20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]HISTIDYL DEXTRO VALYL]CAMPTOTHECIN; 20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]HISTIDYLVALYL]CAMPTOTHECIN; 20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]LYSYL DEXTRO VALYL]CAMPTOTHECIN; 20 O [N ALPHA [4 (3 O METHYL BETA LEVO FUCOPYRANOSYLOXY)PHENYLAMINOTHIOCARBONYL]LYSYLVALYL]CAMPTOTHECIN; AFELETECAN; ANTINEOPLASTIC AGENT; CAMPTOTHECIN DERIVATIVE; GLYCOCONJUGATE; TOPOTECAN; UNCLASSIFIED DRUG;

ACTIVE TRANSPORT; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG DESIGN; DRUG SELECTIVITY; DRUG STABILITY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUMOR GROWTH;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CAMPTOTHECIN; CELLS, CULTURED; DIPEPTIDES; DOGS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FLOW CYTOMETRY; GLYCOCONJUGATES; HEMATOPOIESIS; HEPATOCYTES; HUMANS; MICE; MICE, INBRED C57BL; MICROSCOPY, CONFOCAL; MICROSCOPY, FLUORESCENCE; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSPLANTATION, HETEROLOGOUS; TUMOR CELLS, CULTURED;

EID: 0035935691     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010893l     Document Type: Article

References (20)

1. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata
2. Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer
3. Synthesis and antitumor activity of 20(S)-camptothecin derivatives: Carbamate-linked, water soluble derivatives of 7-ethyl-10-hydroxycamptothecin
4. Synthesis of water-soluble (aminoalky)camptothecin analogues: Inhibition of topoisomerase I and antitumor activity
5. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I
6. Structure activity study of the actions of camptothecin derivatives on mammalian topoisomerase I, evidence for a specific receptor site and for a relation to antitumor activity
7. Preferential binding of the carboxylate form of camptothecin by human serum albumin
8. Pharmacokinetics of camptothecins administered orally
9. Camptothecin antitumor agents
10. Alkyl esters of camptothecin and 9-nitrocamptothecin: Synthesis, in vitro pharmacokinetics, toxicity and antitumor activity
11. Water soluble camptothecin prodrugs
12. Camptothecin delivery systems. Enhanced efficacy and tumor accumulation of camptothecin following its conjugation to poly(ethylene glycol) via a glycine linker
13. Polymer-bound camptothecin: Initial biodistribution and antitumor activity studies
14. Lectin-mediated drug-targeting: Discrimination of carbohydrate mediated cellular uptake between tumor and liver cells with neoglycoconjugates carrying fucose epitopes regioselectively modified in the 3-position
15. Synthesis of 20-O-linked 20(S)-camptothecin glycoconjugates: Impact of the side chain of the ester-linked amino acid on epimerization during the acylation reaction and on hydrolytic stability of the final glycoconjugates
16. Urethane-protected amino acid-N-carboxy anhydrides and their use in peptide synthesis
17. Hepatocyte function and extracellular matrix geometry: Long-term culture sandwich configuration
18. Collagen substrates for studies on cell behaviour
19. 3-D coculture of hepatic sinusoidal cells with primary hepatocytes-design of an organotypical model