Alazopeptin
Alazopeptin is a non-ribosomal tripeptide azoamino acid antibiotic isolated from various Streptomyces species, with significant anti-tumor, antibacterial and trypanocidal activities. Alazopeptin exhibits cytotoxicity against mouse leukemia cells and S-180 tumor cells, inhibits the growth of Bacillus subtilis, and shows activity against Trypanosoma brucei. Alazopeptin can be widely used in studies related to mouse leukemia, S-180 tumor, human African trypanosomiasis and nagana.
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- No. CAS: 1397-84-8
- Fòrmula: C15H20N6O5
- Peso molecular:364.36
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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
Descripciòn
IC50 & Target
[1]|
Trypanosoma |
In Vitro
Alazopeptin exhibits moderate in vitro antitrypanosomal activity and low cytotoxicity against Trypanosoma brucei brucei strain GUTat 3.1 and Trypanosoma brucei rhodesiense strain STIB900[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Trypanosoma brucei brucei strain and Trypanosoma brucei rhodesiense strain STIB900
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Concentration:IC50
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Incubation Time:72 h
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Result:Exhibied Trypanosoma brucei brucei strain GUTat 3.1 (IC50=0.51 μg/mL) and Trypanosoma brucei rhodesiense strain STIB900 (IC50=1.21 μg/mL), with low cytotoxicity against human MRC-5 cells (IC50 >9.10 μg/mL).
In Vivo
Alazopeptin (4.5-36.4 mg/kg; i.v.; daily; 7-10 days) dose-dependently inhibits S-180 solid tumor growth in dd mice[3].
Alazopeptin shows no detectable efficacy against Ehrlich ascites carcinoma in dd mice[3].
Alazopeptin (50 mg/kg; i.p.; daily; 4 consecutive days) does not cure T. b. brucei S427 infection in female ICR mice but increases mean survival day by 1.8-fold relative to controls[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:CDF1 mice with Leukemia (~20 g)[3]
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Dosage:57.3 mg/kg/day; 28.7 mg/kg/day; 14.3 mg/kg/day; 7.2 mg/kg/day; 3.6 mg/kg/day; 1.8 mg/kg/day
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Administration:i.p.; daily; until death
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Result:Achieved a mean survival time (MST) T/C of 23.0/8.0 days, corresponding to an average response of 287% at 57.3 mg/kg/day, with all 6 mice surviving.
Achieved an MST T/C of 16.0/8.0 days (average response 200%) at 28.7 mg/kg/day, with all 6 mice surviving.
Achieved an MST T/C of 14.0/8.0 days (average response 175%) at 14.3 mg/kg/day, with all 6 mice surviving.
Achieved an MST T/C of 13.0/8.0 days (average response 163%) at 7.2 mg/kg/day, with all 6 mice surviving.
Achieved an MST T/C of 11.0/8.0 days (average response 138%) at 3.6 mg/kg/day, with all 6 mice surviving.
Achieved an MST T/C of 8.5/8.0 days (average response 107%) at 1.8 mg/kg/day, with all 6 mice surviving.
Showed better efficacy with daily administration than intermittent administration every 2 days.
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Animal Model:dd mice with Sarcoma[3]
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Dosage:36.4 mg/kg/day (days 1-10); 18.2 mg/kg/day (days 1-10); 9.1 mg/kg/day (days 1-10); 4.5 mg/kg/day (days 1-10); 36.4 mg/kg/day (days 5-11); 18.2 mg/kg/day (days 5-11); 9.1 mg/kg/day (days 5-11); 4.5 mg/kg/day (days 5-11)
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Administration:i.v.; daily; 10 days (days 1-10); 7 days (days 5-11)
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Result:Achieved 100% tumor weight inhibition (tumor weight 0 mg vs control 1401 mg) at 36.4 mg/kg/day (days 1-10), with all 10 mice surviving.
Achieved 99% tumor weight inhibition (tumor weight 8 mg vs control 1401 mg) at 18.2 mg/kg/day (days 1-10), with all 10 mice surviving.
Achieved 89% tumor weight inhibition (tumor weight 158 mg vs control 1401 mg) at 9.1 mg/kg/day (days 1-10), with all 10 mice surviving.
Achieved 21% tumor weight inhibition (tumor weight 1102 mg vs control 1401 mg) at 4.5 mg/kg/day (days 1-10), with all 10 mice surviving.
Achieved 97% tumor weight inhibition (tumor weight 73 mg vs control 2500 mg) at 36.4 mg/kg/day (days 5-11), with all 10 mice surviving.
Achieved 90% tumor weight inhibition (tumor weight 259 mg vs control 2500 mg) at 18.2 mg/kg/day (days 5-11), with all 10 mice surviving.
Achieved 77% tumor weight inhibition (tumor weight 568 mg vs control 2500 mg) at 9.1 mg/kg/day (days 5-11), with all 10 mice surviving.
Achieved 25% tumor weight inhibition (tumor weight 1870 mg vs control 2500 mg) at 4.5 mg/kg/day (days 5-11), with all 10 mice surviving.
Exhibited marked antitumor activity when treatment started 5 days post-transplantation.
Chemical Information
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No. CAS 1397-84-8
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Peso molecular 364.36
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Fòrmula C15H20N6O5
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SMILES
O=C(O)[C@H](CCC(C=[N+]=[N-])=O)NC([C@H](CCC(C=[N+]=[N-])=O)NCC=C)=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]. Ishiyama A, Otoguro K, Namatame M, et al.. In vitro and in vivo antitrypanosomal activitiy of two microbial metabolites, KS-505a and alazopeptin. The Journal of antibiotics. 2008 Oct;61(10):627-32. [Content Brief]
[2]. Kawai S, Moriga K, Nirdnoy W, et al.. Identification of Two Distinct Stereoselective Lysine 5-Hydroxylases by Genome Mining Based on Alazopeptin Biosynthetic Enzymes. Chemistry (Weinheim an der Bergstrasse, Germany). 2025 Apr 04;31(20):e202404790. [Content Brief]
[4]. Kawai S, Katsuyama Y, Ohnishi Y. The α/β Hydrolase AzpM Catalyzes Dipeptide Synthesis in Alazopeptin Biosynthesis Using Two Molecules of Carrier Protein-Tethered Amino Acid. Chembiochem : a European journal of chemical biology. 2022 Apr 05;23(7):e202100700. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Alazopeptin Related Classifications
HY-118965 Related Classifications
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Keywords
- Alazopeptin
- 1397-84-8
- Antibiotic
- Parasite
- Streptacidiphilus griseoplanus
- S-180 tumor cells
- Bacillus subtilis
- Ehrlich ascites carcinoma
- Streptomyces candidus var. azaticus
- Kitasatospora azatica
- human MRC-5 cells
- Trypanosoma brucei brucei
- mouse leukemia L-1210
- Trypanosoma brucei rhodesiense
- Inhibitor
- inhibitor
- inhibit