Annamycin
Annamycin is an anthracycline antibiotic with antitumor activity. Annamycin interacts with topoisomerase II, induces double-strand DNA breaks, triggers cell death, and exerts cytotoxic effects. In mice, Annamycin inhibits the growth of advanced subcutaneous melanoma and subcutaneous squamous cell carcinoma, and prolongs the survival of mice with subcutaneous reticulosarcoma and in lung cancer lung metastasis models. Annamycin can be used in research related to melanoma, reticulum cell sarcoma, lung cancer, non-small cell lung cancer, small cell lung cancer.
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- No. CAS: 92689-49-1
- Fòrmula: C26H25IO11
- Peso molecular:640.37
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Almacenamiento:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Actividad biológica
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Chemical Information
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Actividad biológica
Multidrug-resistant KB-V1, P388/Dox, CEM/Vbl and 8226/R cells exhibit partial loss of cross-resistance to free and multilamellar liposome-encapsulated Annamycin (4 h-72 h)[1].
Annamycin (4.3 min) completely inhibits topoisomerase IIα-mediated DNA cleavage of linearized pBR322 plasmid at an incubation time of 4.3 min[2].
Annamycin (0.1-10 μM; 1 h) potently inhibits P-glycoprotein-mediated efflux in P-gp-expressing cells, with an IC50 of 0.7 μM[2].
Annamycin (4-72 h) circumvents MRP-mediated multidrug resistance in MCF-7, MCF-7/VP, UMCC-1 and UMCC-1/VP cells; it exhibits low resistance indices (1.1, 1.4, 1.3) at 4 and 72 hr exposure durations, with ID50 values ranging from 2.10 to 8.30 μg/mL depending on the cell line and exposure time[3].
Annamycin (5 μg/mL; 1 hr) induces DNA double-strand breaks in MCF-7 cells[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Free Annamycin (4 mg/kg; i.v.; single dose), multilamellar liposomal Annamycin (4 mg/kg; i.v.; single dose), and small unilamellar liposomal Annamycin (4 mg/kg; i.v.; single dose) significantly prolong the survival time of mice subcutaneously inoculated with M5076 reticulosarcoma. Among them, small unilamellar liposome-encapsulated Annamycin (S-Ann) shows the highest efficacy, reaching an ILS of 74.4%[1].
Free Annamycin (4 mg/kg; i.v.; single), multilamellar liposomal Annamycin (4 mg/kg; i.v.; single), and small unilamellar liposomal Annamycin (4 mg/kg; i.v.; single) significantly prolong the survival of mice bearing a Lewis lung carcinoma lung metastasis model. Among them, small unilamellar liposome-encapsulated Annamycin (S-Ann) exerts the optimal efficacy, achieving an 85.3 % ILS at low inoculum dose and a 57.6 % ILS at high inoculum dose, along with the highest long-term tumor-free survival rate[1].
Free Annamycin (4 mg/kg; i.v.; weekly; 3 injections), multilamellar liposomal Annamycin (4 mg/kg; i.v.; weekly; 3 injections), and small unilamellar liposomal Annamycin (4 mg/kg; i.v.; weekly; 3 injections) all inhibit the growth of subcutaneous KB squamous cell carcinoma xenografts, among which small unilamellar liposome-encapsulated Annamycin (S-Ann) shows the highest efficacy, reaching a TGI of 87.8%[1].
Free Annamycin (4 mg/kg; i.v.; weekly; 3 injections), multilamellar liposomal Annamycin (4 mg/kg; i.v.; weekly; 3 injections), and small unilamellar liposomal Annamycin (4 mg/kg; i.v.; weekly; 3 injections) potently inhibit the growth of subcutaneous multidrug-resistant KB-V1 squamous cell carcinoma xenografts. Among them, small unilamellar liposome-encapsulated Annamycin (S-Ann) shows the best efficacy, with a TGI of 92.6% and a 19-fold reduction in tumor growth rate[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6 (male, 7-8 weeks old, inoculated s.c. with 2×106 viable B16 melanoma cells)[1]
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Dosage:5 mg/kg (Free Annamycin); 5 mg/kg (Multilamellar liposomal Annamycin); 5 mg/kg (Small unilamellar liposomal Annamycin)
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Administration:i.v.; single injection
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Result:Produced a %TGI of 65.0 (Free Annamycin).
Produced a %TGI of 67.6 (Multilamellar liposomal Annamycin).
Produced a %TGI of 74.4 (Small unilamellar liposomal Annamycin).
Was significantly more effective than both Free Annamycin and Multilamellar liposomal Annamycin (P < 0.05, Small unilamellar liposomal Annamycin).
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Animal Model:C57BL/6 (male, 7-8 weeks old, inoculated s.c. with 6×105 M5076 reticulosarcoma cells)[1]
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Dosage:4 mg/kg (Free Annamycin); 4 mg/kg (Multilamellar liposomal Annamycin); 4 mg/kg (Small unilamellar liposomal Annamycin)
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Administration:i.v.; single injection
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Result:Produced a %ILS of 45.6 (Free Annamycin).
Produced a %ILS of 63.2 (Multilamellar liposomal Annamycin).
Produced a %ILS of 74.4 (Small unilamellar liposomal Annamycin).
Was significantly more effective than doxorubicin (all Annamycin formulations).
Was significantly more effective than Multilamellar liposomal Annamycin and Free Annamycin (P < 0.01 between any two groups, Small unilamellar liposomal Annamycin).
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Animal Model:C57BL/6×DBA2 F1 (B6D2F1) (male, 7 weeks old, inoculated i.v. with 3.6×105 or 1×106 Lewis lung carcinoma cells)[1]
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Dosage:4 mg/kg (Free Annamycin); 4 mg/kg (Multilamellar liposomal Annamycin); 4 mg/kg (Small unilamellar liposomal Annamycin)
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Administration:i.v.; single injection
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Result:Produced a %ILS of 39.2 with 4/10 long-term survivors (Free Annamycin, low inoculum group).
Produced a %ILS of 73.5 with 7/10 long-term survivors (Multilamellar liposomal Annamycin, low inoculum group).
Produced a %ILS of 85.3 with 8/10 long-term survivors (Small unilamellar liposomal Annamycin, low inoculum group).
Produced a %ILS of 18.7 (Free Annamycin, high inoculum group).
Produced a %ILS of 26.7 (Multilamellar liposomal Annamycin, high inoculum group).
Produced a %ILS of 57.6 (Small unilamellar liposomal Annamycin, high inoculum group).
Was significantly more effective than doxorubicin (all Annamycin formulations).
Was significantly more effective than Multilamellar liposomal Annamycin and Free Annamycin (P < 0.01 between any two groups, Small unilamellar liposomal Annamycin).
Confirmed no tumor presence in long-term survivors (autopsy).
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Animal Model:nude (nu/nu) (male, 7-8 weeks old, inoculated s.c. with 0.4×106 KB squamous cell carcinoma cells)[1]
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Dosage:4 mg/kg per injection, total 12 mg/kg (Free Annamycin); 4 mg/kg per injection, total 12 mg/kg (Multilamellar liposomal Annamycin); 4 mg/kg per injection, total 12 mg/kg (Small unilamellar liposomal Annamycin)
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Administration:i.v.; weekly; 3 injections
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Result:Produced a %TGI of 78.6 (Free Annamycin).
Produced a %TGI of 83.2 (Multilamellar liposomal Annamycin).
Produced a %TGI of 87.8 (Small unilamellar liposomal Annamycin).
Was significantly more effective than Free Annamycin and doxorubicin (P < 0.05, Small unilamellar liposomal Annamycin).
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Animal Model:nude (nu/nu) (male, 7-8 weeks old, inoculated s.c. with 5.8×106 KB-V1 multidrug-resistant squamous cell carcinoma cells)[1]
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Dosage:4 mg/kg per injection, total 12 mg/kg (Free Annamycin); 4 mg/kg per injection, total 12 mg/kg (Multilamellar liposomal Annamycin); 4 mg/kg per injection, total 12 mg/kg (Small unilamellar liposomal Annamycin)
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Administration:i.v.; weekly; 3 injections
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Result:Produced a %TGI of 82.3 and reduced tumor growth rate 7-fold compared to controls (Free Annamycin).
Produced a %TGI of 86.4 and reduced tumor growth rate 8-fold compared to controls (Multilamellar liposomal Annamycin).
Produced a %TGI of 92.6 and reduced tumor growth rate 19-fold compared to controls (Small unilamellar liposomal Annamycin).
Was significantly more effective than doxorubicin (P < 0.01, all Annamycin formulations).
Was significantly more effective than Free Annamycin (P < 0.01) and Multilamellar liposomal Annamycin (P < 0.05, Small unilamellar liposomal Annamycin).
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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No. CAS 92689-49-1
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Peso molecular 640.37
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Fòrmula C26H25IO11
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SMILES
O=C1C2=C(C(C3=CC=CC=C31)=O)C(O)=C(C4=C2O)C[C@@](C(CO)=O)(C[C@@H]4O[C@@]5(O[C@H]([C@@H]([C@H]([C@H]5I)O)O)C)[H])O
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
Referencias
[1]. Zou Y, et al. Antitumor activity of free and liposome-entrapped annamycin, a lipophilic anthracycline antibiotic with non-cross-resistance properties. Cancer Res. 1994 Mar 15;54(6):1479-84. [Content Brief]
[2]. Booser DJ, et al. Phase I study of liposomal annamycin. Cancer Chemother Pharmacol. 2000;46(5):427-32. [Content Brief]
[3]. Perez-Soler R, et al. Annamycin circumvents resistance mediated by the multidrug resistance-associated protein (MRP) in breast MCF-7 and small-cell lung UMCC-1 cancer cell lines selected for resistance to etoposide. Int J Cancer. 1997;71(1):35-41. [Content Brief]
Calculators
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