| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 25mg | |||
| Other Sizes |
| Targets |
Sangivamycin targets multiple enzymes: it inhibits protein kinase C (PKC) by competing with ATP, with an IC50 in the low micromolar range. It also inhibits cyclin-dependent kinases (CDKs) and other serine/threonine kinases. As a nucleoside analog, it is phosphorylated intracellularly to its triphosphate form, which inhibits RNA synthesis by competing with GTP and ATP. This dual mechanism leads to disruption of cell proliferation and induction of apoptosis.
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| ln Vitro |
Antitumor effects Sanjivamycin (0.3 μM; 0-72 hours) shows almost maximal cell killing (for MCF7/ADR) or cell growth inhibition (for MCF7/WT) effects. Sangemycin has differential antitumor effects in drug-sensitive MCF7/wild-type (WT) tumor cells, leading to growth induction. Use of MCF7/doxorubicin (ADR) in drugs has differential antitumor effects in human breast cancer cells. Caspases in cells MCF7/ADR. Within 48 hours of Sangivamycin (0.3 μM) exposure, lamin A was found in significant levels, broken into 28 kDa pieces, in MCF7/ADR cells [2].
In vitro, sangivamycin exhibits potent cytotoxic activity against various cancer cell lines, including leukemia (HL-60, K562), breast (MCF-7), and lung (A549) cancer cells, with IC50 values typically in the nanomolar to low micromolar range. It inhibits the growth of protozoan parasites such as Trypanosoma brucei and Leishmania species. Its antiviral activity has been demonstrated against herpes simplex virus and hepatitis C virus. The compound also suppresses the proliferation of T cells and has immunosuppressive effects. |
| ln Vivo |
In vivo, sangivamycin has shown antitumor activity in murine models of leukemia and solid tumors. In mice bearing L1210 leukemia, sangivamycin prolonged survival when administered intraperitoneally. It also reduced tumor growth in xenograft models of human colon and breast cancers. However, its therapeutic index is narrow, and toxicity limits its clinical use. In animal models of African trypanosomiasis, sangivamycin demonstrated antiparasitic efficacy.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for sangivamycin include PKC inhibition assays using purified PKC isoforms and a radioactive ATP substrate; the IC50 for each isoform is determined. Its ability to inhibit CDKs can be assessed using recombinant CDK/cyclin complexes. The compound's binding to ATP-binding sites can be studied using surface plasmon resonance. Its incorporation into RNA can be measured using radiolabeled sangivamycin.
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| Cell Assay |
In vitro cellular assays for sangivamycin are performed using cancer cell lines. Cells are treated with varying concentrations, and cell viability is measured by MTT or resazurin reduction assays. Apoptosis is evaluated by annexin V staining, caspase activity, and DNA fragmentation. Cell cycle analysis is performed by flow cytometry. RNA synthesis inhibition is measured by incorporation of radiolabeled uridine. Kinase inhibition is confirmed by Western blotting for phospho-substrates.
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| Animal Protocol |
In vivo animal experiments for sangivamycin are conducted in mouse models. For antitumor efficacy, mice are injected with tumor cells (e.g., L1210) and then treated with sangivamycin intraperitoneally or intravenously. Survival, tumor size, and histopathology are assessed. For antiparasitic efficacy, mice infected with T. brucei are treated, and parasitemia is monitored. Pharmacokinetic and toxicology studies are also performed in rodents.
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| ADME/Pharmacokinetics |
Sangivamycin has a molecular weight of 307.26 g/mol and a molecular formula of C12H13N5O4. It is a yellow to off-white crystalline powder, soluble in water and organic solvents. It is a nucleoside analog similar to adenosine. Pharmacokinetic data are limited; in mice, it has a short half-life (approximately 30 minutes) and is rapidly cleared. It is metabolized by deamination and excreted in urine. Its oral bioavailability is poor, so it is administered parenterally.
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| Toxicity/Toxicokinetics |
Sangivamycin has significant toxicity, including dose-limiting myelosuppression, gastrointestinal effects, and hepatotoxicity. In preclinical studies, the therapeutic index was narrow, with severe toxicity at doses near the effective dose. It has been reported to cause weight loss, lethargy, and histopathological changes in liver and bone marrow. Due to its toxicity, clinical development has been limited. It is handled as a hazardous compound in research.
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| References |
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| Additional Infomation |
Sanggymycin is a nucleoside analogue, a derivative of adenosine, in which the nitrogen atom at position 7 is replaced by a carbamoyl group on the carbon atom. It is a potent inhibitor of protein kinase C, exhibiting protein kinase inhibitory activity. Its function is similar to that of adenosine. Sanggymycin has been reported in Streptomyces and Streptomyces sparsely, and relevant data are available for reference.
Sangivamycin is a nucleoside analog with potent but non-selective kinase inhibition and cytotoxic effects. It has been investigated as a potential anticancer and antiparasitic agent but was not approved due to toxicity. Its structure has inspired the development of more selective analogs. Sangivamycin is used primarily as a research tool to study PKC signaling and nucleoside metabolism. It is also used as a reference compound for antiviral and antiparasitic drug discovery. |
| Molecular Formula |
C12H15N5O5
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|---|---|
| Molecular Weight |
309.28
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| Exact Mass |
327.118
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| CAS # |
18417-89-5
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| PubChem CID |
14978
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| Appearance |
White to off-white solid powder
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| Boiling Point |
880.6ºC at 760 mmHg
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| Flash Point |
486.4ºC
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| Vapour Pressure |
3.3E-33mmHg at 25°C
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| LogP |
-2.5
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
22
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| Complexity |
440
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C(=O)N
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| InChi Key |
OBZJZDHRXBKKTJ-JTFADIMSSA-N
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| InChi Code |
InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1
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| Chemical Name |
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
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| Synonyms |
B-90912 B 90912 Sangivamycin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~323.33 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.08 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2333 mL | 16.1666 mL | 32.3332 mL | |
| 5 mM | 0.6467 mL | 3.2333 mL | 6.4666 mL | |
| 10 mM | 0.3233 mL | 1.6167 mL | 3.2333 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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