CAS 66584-72-3|Ansamitocin P-3
Introduction：Basic information about CAS 66584-72-3|Ansamitocin P-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Ansamitocin P-3 | ||
|---|---|---|---|
| CAS Number | 66584-72-3 | Molecular Weight | 635.145 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 833.1±65.0 °C at 760 mmHg |
| Molecular Formula | C32H43ClN2O9 | Melting Point | 190-192℃ |
| MSDS | ChineseUSA | Flash Point | 457.7±34.3 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | ansamitocin P3 |
|---|---|
| Synonym | More Synonyms |
Ansamitocin P-3 BiologicalActivity
| Description | Ansamitocin P-3 is a microtubule inhibitor. Ansamitocin P-3 is a macrocyclic antitumor antibiotic. |
|---|---|
| Related Catalog | Signaling Pathways >>Antibody-drug Conjugate >>ADC CytotoxinSignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinNatural Products >>OthersResearch Areas >>Cancer |
| Target | Microtubule[1] |
| In Vitro | Ansamitocin P3 potently inhibits the proliferation of MCF-7, HeLa, EMT-6/AR1 and MDA-MB-231 cells in culture with a half-maximal inhibitory concentration of 20±3, 50±0.5, 140±17, and 150±1.1 pM, respectively. Further, Ansamitocin P3 is found to bind to purified tubulin in vitro with a dissociation constant (Kd) of 1.3±0.7 µM. The binding of Ansamitocin P3 induces conformational changes in tubulin. Ansamitocin P3 inhibits the proliferation of MCF-7, HeLa, EMT-6/AR1 and MDA-MB-231 cells in culture in a concentration dependent manner. Flow cytometric analysis of PI-stained cells suggests that Ansamitocin P3 inhibits the cell cycle progression of MCF-7 cells in G2/M phase. For example, 26, 50 and 70% of the cells are found to be in G2/M phase in the absence and presence of 50 and 100 pM Ansamitocin P3, respectively[2]. |
| Cell Assay | MCF-7, EMT-6/AR1, HeLa and MDA-MB-231 cells are seeded in 96 well plates. Subsequently, cells are incubated with vehicle (0.1% DMSO) or different concentrations (1-1000 pM) of Ansamitocin P3 for 48 h in MCF-7 cells and 24 h for EMT-6/AR1, HeLa and MDA-MB-231 cells, respectively. The half maximal inhibitory concentration of cell proliferation (IC50) for Ansamitocin P3 is determined by sulforhodamine B assay. Four independent experiments are carried out in MCF-7 cells and three independent sets of experiments are performed in EMT-6/AR1, HeLa and MDA-MB-231 cells[2]. |
| References | [1]. Kiso T, et al. Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. Antimicrob Agents Chemother. 2004 May;48(5):1739-48. [2]. Venghateri JB, et al. Ansamitocin P3 depolymerizes microtubules and induces apoptosis by binding to tubulin at thevinblastine site. PLoS One. 2013 Oct 4;8(10):e75182. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 833.1±65.0 °C at 760 mmHg |
| Melting Point | 190-192℃ |
| Molecular Formula | C32H43ClN2O9 |
| Molecular Weight | 635.145 |
| Flash Point | 457.7±34.3 °C |
| Exact Mass | 634.265686 |
| PSA | 136.16000 |
| LogP | 5.09 |
| Vapour Pressure | 0.0±3.2 mmHg at 25°C |
| Index of Refraction | 1.583 |
| InChIKey | OPQNCARIZFLNLF-JSPHAMTJSA-N |
| SMILES | COc1cc2cc(c1Cl)N(C)C(=O)CC(OC(=O)C(C)C)C1(C)OC1C(C)C1CC(O)(NC(=O)O1)C(OC)C=CC=C(C)C2 |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 625 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
MUTATION DATA - TYPE OF TEST :
- Cytogenetic analysis
- TEST SYSTEM :
- Rodent - mouse Ascites tumor
- DOSE/DURATION :
- 4 ug/kg
- REFERENCE :
- CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 40,1707,1980
- TYPE OF TEST :
- Cytogenetic analysis
- TEST SYSTEM :
- Rodent - mouse Ascites tumor
- DOSE/DURATION :
- 4 ug/kg
- REFERENCE :
- CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 40,1707,1980
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H315-H319-H332-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn |
| Risk Phrases | 20/22-36/37/38 |
| Safety Phrases | 26-36 |
| RIDADR | NONH for all modes of transport |
| RTECS | OQ2293000 |
Articles28
More Articles| Enhanced production of ansamitocin P-3 by addition of isobutanol in fermentation of Actinosynnema pretiosum. Bioresour. Technol. 102 , 1863-1868, (2011) Supply of isobutanol to enhance the production of anti-tumor agent ansamitocin P-3 (AP-3) in medium containing agro-industrial residues was investigated with analysis of gene transcription, enzyme act... | |
| Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins. Chem. Biol. 15(8) , 863-74, (2008) Ansamitocins are potent antitumor maytansinoids produced by Actinosynnema pretiosum. Their biosynthesis involves the initial assembly of a macrolactam polyketide, followed by a series of postpolyketid... | |
| Determination of the cryptic stereochemistry of the first PKS chain-extension step in ansamitocin biosynthesis by Actinosynnema pretiosum. ChemBioChem. 7(8) , 1221-5, (2006) The biosynthesis of the antitumor antibiotic, ansamitocin, involves the assembly of a linear octaketide on the ansamitocin (asm) polyketide synthase (PKS), which is then cyclized to proansamitocin and... |
Synonyms
| Ansamitosin P 3 |
| Propanoic acid, 2-methyl-, (1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester |
| ANSAMITOCIN P-3 |
| Tam-330 |
| (1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate |
| 2'-De(acetylmethylamino)-2'-methylmaytansine |
| Propanoic acid, 2-methyl-, (1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester |
| Anasamitocin P-3 |
| (1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate |
| Maytansinol isobutyrate |
| O3-isobutyryl-maytansinol |
| (3E,5E,7R,84S)-14-chloro-10t,11c-epoxy-84-hydroxy-12c-isobutyryl-15,7r-dimethoxy-3,9c,11t,15-tetramethyl-(84r'H,86c'H)-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione |
