Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone.

Literature DB >> 168385

Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone.

F Arcamone, S Penco, A Vigevani, S Redaelli, G Franchi, A DiMarco, A M Casazza, T Dasdia, F Formelli, A Necco, C Soranzo.

Abstract

The synthesis of 4'-epi-daunorubicin and of 4'-epi-adriamycin was performed by condensation of 2,3,6-trideoxy-3-trifluoroacetamido-4-O-trifluoroacetyl-alpha-L-arabino-hexopyranosyl chloride with daunomycinone or the protected adriamycinone derivative 17, respectively. Both the alpha and beta anomers were obtained and characterized. All new compounds are biologically active in cultured cells and the alpha anomers display noticeable activity in experimental tumors in mice. Interestingly, 4'-epi-adriamycin (4) appears nontoxic to cultured heart cells up to a concentration of 5 mug/ml.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 1975 PMID： 168385 DOI： 10.1021/jm00241a013

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

Keyword Cloud
Cited

33 in total

1. Comparative effects of doxorubicin and 4'-epi-doxorubicin on nucleic acid metabolism and cytotoxicity in a human tumor cell line.

Authors: O Cantoni; P Sestili; F Cattabeni; C Geroni; F Giuliani
Journal: Cancer Chemother Pharmacol Date: 1990 Impact factor: 3.333

2. Hemodynamic effects of chronic 4'epi-adriamycin administration.

Authors: J Milei; J J Ale; G Garay; F Otero; A Z Comba; H O Gugliotta; R A Storino
Journal: Cardiovasc Drugs Ther Date: 1990-12 Impact factor: 3.727

3. TOP2A amplification in the absence of that of HER-2/neu: toward individualization of chemotherapeutic practice in breast cancer.

Authors: Ronan W Glynn; Sarah Mahon; Catherine Curran; Grace Callagy; Nicola Miller; Michael J Kerin
Journal: Oncologist Date: 2011-06-24

Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone.

1. Comparative effects of doxorubicin and 4'-epi-doxorubicin on nucleic acid metabolism and cytotoxicity in a human tumor cell line.

2. Hemodynamic effects of chronic 4'epi-adriamycin administration.

3. TOP2A amplification in the absence of that of HER-2/neu: toward individualization of chemotherapeutic practice in breast cancer.

4. Cellular and molecular pharmacology of 4'-epidoxorubicin in HeLa cells. Comparison with its parent drug, doxorubicin.

5. Intravesical chemotherapy with 4'-epi-Adriamycin in patients with superficial bladder tumors.

6. Biliary excretion and pharmacokinetics of 4'epidoxorubicin (epirubicin) in advanced cancer patients.

7. Phase-II clinical trial of 4'-epi-doxorubicin in metastatic solid tumors.

Review 8. Anthracycline antitumour agents. A review of physicochemical, analytical and stability properties.

Review 9. Epirubicin. Clinical pharmacology and dose-effect relationship.

10. Comparative metabolism and elimination of adriamycin and 4'-epiadriamycin in the rat.