Mithramycin A structure
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Common Name | Mithramycin A | ||
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CAS Number | 18378-89-7 | Molecular Weight | 1085.145 | |
Density | 1.5±0.1 g/cm3 | Boiling Point | 1169.8±65.0 °C at 760 mmHg | |
Molecular Formula | C52H76O24 | Melting Point | 180-183ºC | |
MSDS | Chinese USA | Flash Point | 327.4±27.8 °C | |
Symbol |
GHS07 |
Signal Word | Warning |
Use of Mithramycin APlicamycin is a selective specificity protein 1 (Sp1) inhibitor. Plicamycin inhibits the growth of various cancers by decreasing Sp1 protein. |
Name | mithramycin |
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Synonym | More Synonyms |
Description | Plicamycin is a selective specificity protein 1 (Sp1) inhibitor. Plicamycin inhibits the growth of various cancers by decreasing Sp1 protein. |
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Related Catalog | |
Target |
Sp1 transcription factor[1] |
In Vitro | Sp1 is a zinc-finger transcription factor that regulates multiple cellular functions and promotes tumor progression by controlling expression of genes involved in cell cycle, apoptosis and DNA damage. Sp1 binds to GC-rich motifs of promoters and interacts with components of the general transcriptional machinery and co-activator complexes of multiple signaling pathways. Plicamycin (Mith) decreases Sp1 protein by inducing proteasome-dependent degradation, thereby suppressing cervical cancer growth through a DR5/caspase-8/Bid signaling pathway. To assess the antiproliferative effects of Plicamycin on cervical cancer cells, two cervical cancer cell lines with different genetic backgrounds are grown with or without treatment with Plicamycin at different concentrations. Plicamycin inhibits HEp-2 and KB cell growth in a concentration-dependent manner after 48 h. Apoptotic cell death is qualitatively estimated by DAPI staining for nuclear condensation and fragmentation. Plicamycin leads to significant DNA fragmentation compared to untreated controls[1]. |
In Vivo | The antitumorigenic activity of Plicamycin (0.2 mg/kg/day) is determined in a xenograft model and observed reduction in tumor volume and weight. No significant mouse body weight loss is observed in Plicamycin-treatment groups, indicating that Plicamycin-associated toxicity is minimal. Plicamycin also increases TUNEL-positive cells in tumor xenografts. No notable intergroup differences are observed among organs, indicating no marked signs of systemic toxicity at the Plicamycin dose used in this study[1]. |
Cell Assay | HEp-2 cells and KB cells are cultured in DMEM 100 U/mL each of Penicillin and Streptomycin and 10% FBS for HEp-2 cells and 5% FBS for KB in a humidified atmosphere containing 5% CO2 at 37°C. Equal numbers of cells are seeded and allowed to attach. At 50-60% confluence, cells are treated with DMSO or indicated concentrations of Plicamycin (50, 100, and 200 nM for HEp-2 cells; 20, 40, and 80 nM for KB cells). Cell viability is determined using CellTiter 96 Aqueous One Solution Cell Proliferation Assay Kits. In brief, cells are seeded in 96-well plates and incubated with Plicamycin. After treatment, 30 µL MTS solution is added to each well and cells are incubated for 2 h at 37°C. MTS solution is analyzed using a microplate reader at 490 nm and 690 nm[1]. |
Animal Admin | Mice[1] Female nude mice are used. KB cells are suspended in sterile PBS and injected subcutaneously into the right flank of mice. Mice are randomized into two groups containing five mice each and treated with 0.2 mg/kg/day of Plicamycin (i.p.) three times per week for 29 days. Control mice receive an equal volume of vehicle. After 29 days, bodies, organs and tumors are weighed and tumor volumes determined. Tumors are measured[1]. |
References |
Density | 1.5±0.1 g/cm3 |
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Boiling Point | 1169.8±65.0 °C at 760 mmHg |
Melting Point | 180-183ºC |
Molecular Formula | C52H76O24 |
Molecular Weight | 1085.145 |
Flash Point | 327.4±27.8 °C |
Exact Mass | 1084.472656 |
PSA | 358.20000 |
LogP | 1.29 |
Vapour Pressure | 0.0±0.3 mmHg at 25°C |
Index of Refraction | 1.640 |
Synonym:Aureolic Acid; Plicamycin Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
Risk Phrases: 23/24/25 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. Moderately toxic to humans by ingestion. The toxicological properties of this substance have not been fully investigated. May cause anemia, leukopenia (reduction in the number of white blood cells in the blood), and thrombocytopenia. Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Chronic: No information found. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.) Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 18378-89-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: yellow crystalline powder Odor: none reported pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 180.00 - 183.00 deg C Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: soluble in water Specific Gravity/Density: Molecular Formula: C52H76O24 Molecular Weight: 1085.16 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, dust generation, excess heat, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 18378-89-7: PZ2800000 LD50/LC50: CAS# 18378-89-7: Oral, mouse: LD50 = 500 mg/kg. TDLo -Oral, Human: 50 Carcinogenicity: Plicamycin - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.* Hazard Class: 6.1 UN Number: 2811 Packing Group: III IMO Shipping Name: TOXIC SOLID, ORGANIC, N.O.S. Hazard Class: 6.1 UN Number: 2811 Packing Group: III RID/ADR Shipping Name: TOXIC SOLID, ORGANIC, N.O.S. Hazard Class: 6.1 UN Number: 2811 Packing group: III Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: T Risk Phrases: R 23/24/25 Toxic by inhalation, in contact with skin and if swallowed. Safety Phrases: S 28A After contact with skin, wash immediately with plenty of water. S 36/37/39 Wear suitable protective clothing, gloves and eye/face protection. S 37 Wear suitable gloves. S 38 In case of insufficient ventilation, wear suitable respiratory equipment. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 18378-89-7: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 18378-89-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 18378-89-7 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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Symbol |
GHS07 |
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Signal Word | Warning |
Hazard Statements | H302 |
Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Faceshields;Gloves |
Hazard Codes | Xn: Harmful; |
Risk Phrases | R22 |
Safety Phrases | 45-38-36/37/39-28A-22 |
RIDADR | UN 3249 |
WGK Germany | 3 |
RTECS | PZ2800000 |
Packaging Group | III |
Hazard Class | 6.1(b) |
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Antibiotic LA-7017 |
D-threo-2-Pentulose, 5-deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-, (1S)- |
aurlelicacid |
MFCD00135618 |
EINECS 232-455-8 |
MITHRAMYCIN |
Mithramycin A From Streptomyces Argillaceus |
aurelicacid |
(1S)-5-Deoxy-1-C-[(2S,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl]-1-O-methyl-D-xylulose |
(1S)-5-Deoxy-1-C-[(2R,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl]-1-O-methyl-D-xylulose |
PlicatoMycin |
a-2371 |
D-threo-2-Pentulose, 5-deoxy-1-C-[(3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-O-2,6 -dideoxy-β-D-arabino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-, (1S)- |
mitramycin |
(1S)-5-Deoxy-1-C-[(3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arab ino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydro-2-anthracenyl]-1-O-methyl-D-xylulose |
(1S)-5-Deoxy-1-C-[(2R,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydro-2-anthracenyl]-1-O-methyl-D-xylulose |
pa144 |
AURLELIC ACID |
Aurelic acid |
PLICAMYCIN |
MITHRACIN |
Mithramycin A,(1S)-5-Deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1.fwdarw.3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1.fwdarw.3)-2,6-dideo |
aureolic acid |
Mithramycin A |