Annamycin - CAS 92689-49-1
Catalog number: 92689-49-1
Category: Inhibitor
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Molecular Formula:
C26H25IO11
Molecular Weight:
640.379
COA:
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Description:
Annamycin liposomal is a liposome-encapsulated form of the semi-synthetic doxorubicin analogue annamycin with antineoplastic activity. Annamycin intercalates into DNA and inhibits topoisomerase II, resulting in the inhibition of DNA replication and repair and RNA and protein synthesis. Liposomal annamycin is less toxic and shows improved antitumor activity compared to annamycin.
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InChIKey:
CIDNKDMVSINJCG-GKXONYSUSA-N
InChI:
InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1
Canonical SMILES:
CC1C(C(C(C(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)CO)O)I)O)O
Current Developer:
Callisto Pharmaceuticals
1.Effect of structural modification at the 4, 3', and 2' positions of doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity in human melanoma cells.
Gruber BM1, Anuszewska EL, Bubko I, Goździk A, Fokt I, Priebe W. Arch Immunol Ther Exp (Warsz). 2007 May-Jun;55(3):193-8. Epub 2007 Jun 8.
INTRODUCTION: The mechanism of the cytotoxicity of anthracyclines is pleiotropic and its significance in cell growth inhibition seems to be highly specific and dependent on cell type and anthracycline drug. Resistance and the high cardiotoxicity of anthracyclines have stimulated many studies aimed at identifying critical substituents required for optimal activity. Many authors point to the fact that the double-strand breaks, the consequence of the activity of topoisomerase II poisons, and the inability of cells to repair the DNA lesions are the signal for apoptosis. The aim of this study was to define the influence of 4-demetoxy 2'-halogenated analogs with altered basicity at the 3'-position on topoisomerase II and the relationship of that interaction with apoptosis and the cytotoxicity of these novel anthracyclines. Parental human ME18 melanoma cells and the ME18/R subline, obtained experimentally, resistant to doxorubicin (DOX), exposed to 1.
2.Phase II study of liposomal annamycin in the treatment of doxorubicin-resistant breast cancer.
Booser DJ1, Esteva FJ, Rivera E, Valero V, Esparza-Guerra L, Priebe W, Hortobagyi GN. Cancer Chemother Pharmacol. 2002 Jul;50(1):6-8. Epub 2002 May 21.
Liposomal annamycin (L-AN) has shown antitumor activity in preclinical studies. It may selectively target tumors and bypass MDR-1 resistance. A total of 13 women with doxorubicin-resistant breast cancer were treated on this phase II study. The median number of prior chemotherapy regimens was two, and six patients had two or more organ sites of involvement. L-AN was administered at 190-250 mg/m(2) as an i.v. infusion over 1-2 h every 3 weeks. No responses were observed. Of the 13 patients, 12 had clear deterioration and new tumor growth after one or two courses. The 13th patient had prolonged grade 2 thrombocytopenia after one course, and was taken off study when the lung metastases increased 62 days after treatment. L-AN at this dose and on this schedule had no detectable antitumor activity in patients with doxorubicin-resistant metastatic breast cancer.
3.Topoisomerase II alpha expression and cytotoxicity of anthracyclines in human neoplastic cells.
Gruber BM1, Anuszewska EL, Roman I, Goździk A, Priebe W, Fokt I. Acta Pol Pharm. 2006 Jan-Feb;63(1):15-8.
Topoisomerase II is ATP dependent enzyme that catalyzes DNA strand passage, the pivotal process in replication, transcription, recombination etc. As part of this breakage and religation process the intermediate generated is a cleavable complex between DNA and topoisomerase II. This complex is the target for topoisomerase II inhibitors like epipodophyllotoxins, actinomycin D or anthracyclines. Stabilization of cleavable complexes by the topoisomerase II inhibitors leading to DNA lesions and next to apoptosis is the most common mechanism of drug resistance reflected in reduced formation of the complexes due to decreased amounts and/or activity of topoisomerase II. The aim of this study was to characterize human melanoma and human cervix carcinoma cells differing in sensitivity to doxorubicin and anthracycline analogs, annamycin and WP903 for topoisomerase IIalpha protein and gene expression with use of Western blot and RT- PCR. As shown, no significant differences in topoisomerase IIalpha protein level were noted between the cell lines tested.
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CAS 92689-49-1 Annamycin

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