Distamycin A hydrochloride
Distamycin A hydrochloride (NSC-82150 hydrochloride) is an oligopeptide pyrrole antibiotic. Distamycin A hydrochloride inhibits DNA-dependent DNA polymerase and inhibits DNA-dependent RNA polymerase by blocking sigma-dependent initiation complex formation. Distamycin A hydrochloride exhibits antiviral activity against DNA viruses, antibacterial activity against Gram-positive bacteria and fungi, and antiproliferative activity against leukemia cells. Distamycin A hydrochloride can be used in research on viral infections, leukemia, and cancer.
For research use only. We do not sell to patients.
- CAS No.: 6576-51-8
- Formula: C22H28ClN9O4
- Molecular Weight:517.97
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
Description
In Vitro
Distamycin A (6-20 μM) hydrochloride inhibits DNA-dependent DNA polymerase (from Ehrlich ascites tumor cells) at 6 μM by binding to the DNA template, and inhibits RNA polymerase (from Escherichia coli) with a 50% inhibitory concentration of 10-20 μM[4].
Distamycin A (20 h) hydrochloride induces resistance in Bacillus subtilis strains PB 1689, PB 1717, and PB 1718, with a minimum inhibitory concentration of 200 μg/mL, compared to 20 μg/mL for the parental strain PB 202[7].
Distamycin A (50 μg/mL) hydrochloride induces a dst-3 mutation in Bacillus subtilis PB 1689, conferring resistance to growth inhibition, with the mutant being affected only at doses above 100 μg/mL compared to 50 μg/mL for the parental strain PB 202[7].
Distamycin A (48 h) hydrochloride shows cross-resistance in both Doxorubicin (HY-15142A)- and Tallimustine (HY-105270)-resistant L1210 leukemia cell lines, with IC50 values of 459 μM and 142 μM, respectively[6].
Distamycin A hydrochloride shows similar effectiveness against SV40 DNA and calf thymus DNA in RNA polymerase assays[1].
Distamycin A (20-80 µM; 15 min) hydrochloride selectively inhibits the binding of transcription factors SRF and MEF2 to their respective A/T-rich elements in nuclear extracts of C2C12 myotubes, without affecting the binding of Sp1 or MyoD[2].
Distamycin A (20-40 µg/mL; 3 days) hydrochloride reversibly inhibits the morphological differentiation of C2 myoblasts without significantly affecting cell growth[2].
Distamycin A (20-40 µg/mL; 7 days) hydrochloride enhances adipocyte differentiation by approximately 4-fold in pluripotent TA1 cells while inhibiting myogenic differentiation by 85%[2].
Distamycin A (40 µg/mL) hydrochloride strongly downregulates endogenous muscle-specific gene transcripts (cardiac α-actin, skeletal α-actin, myosin heavy chain, and myoD1) in differentiating C2 cells without affecting non-muscle gene transcripts[2].
Distamycin A (40 µg/mL; 48 h) hydrochloride inhibits human cardiac α-actin promoter activity by 73% and human skeletal muscle α-actin promoter activity by 35% in C2 cells, while it does not inhibit the β-actin or c-fos promoter[2].
Distamycin A (20-80 µg/mL; 48 h) hydrochloride inhibits the human cardiac α-actin promoter in a dose-dependent manner in CV-1 cells, even upon ectopic expression of myoD, indicating that this inhibition is not due to suppression of myoD expression[2].
Distamycin A (40 µg/mL; 48 h) hydrochloride selectively inhibits MEF2-dependent promoter activity by 82% in CV-1 cells, while it does not inhibit MyoD-dependent promoter activity[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:C2
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Concentration:20 µg/mL; 40 µg/mL
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Incubation Time:3 days; 48 h (reversibility)
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Result:Eliminated morphological differentiation at 20-40 µg/mL.
Displayed less than 1% of cells fused into myotubes at 40 µg/mL compared to greater than 95% fusion in control cells.
Showed minimal effect upon C2 myoblast growth at 40 µg/mL or lower.
Completely reversed inhibition of cellular differentiation following removal and additional 48 h culture.
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Cell Line:TA1
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Concentration:20-40 µg/mL
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Incubation Time:7 days
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Result:Increased lipid producing cells approximately 4-fold at 40 µg/mL.
Repressed myogenic differentiation by 85% at 40 µg/mL.
Chemical Information
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CAS No. 6576-51-8
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Molecular Weight 517.97
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Formula C22H28ClN9O4
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SMILES
O=CNC1=CN(C)C(C(NC2=CN(C)C(C(NC3=CN(C)C(C(NCCC(N)=N)=O)=C3)=O)=C2)=O)=C1.Cl
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Synonyms
NSC-82150 hydrochloride
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[5]. Beria I, et al. Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. Journal of medicinal chemistry. 2004 May 06;47(10):2611-23. [Content Brief]
[6]. Baraldi PG, et al. Synthesis and antitumor activity of new benzoheterocyclic derivatives of distamycin A. Journal of medicinal chemistry. 2000 Jul 13;43(14):2675-84. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Keywords
- Distamycin A
- 6576-51-8
- NSC-82150
- NSC82150
- NSC 82150
- Antibiotic
- Bacterial
- Fungal
- Nucleoside Antimetabolite/Analog
- DNA/RNA Synthesis
- Gram-positive bacteria
- E. coli RNA polymerase
- DNA-dependent RNA polymerase
- double-stranded B-DNA
- Rauscher murine leukemia virus reverse transcriptase
- leukemia cells
- A-T-rich regions
- DNA-dependent DNA polymerase
- L1210 murine leukemia cells
- Ehrlich ascites tumor cells
- Inhibitor
- inhibitor
- inhibit