Ansamitocin P-3

Modify Date: 2024-01-02 07:38:19

Ansamitocin P-3 Structure
Ansamitocin P-3 structure
 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 Chinese USA Flash Point 457.7±34.3 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ansamitocin P-3


Ansamitocin P-3 is a microtubule inhibitor. Ansamitocin P-3 is a macrocyclic antitumor antibiotic.

 Names

Name ansamitocin P3
Synonym More Synonyms

 Ansamitocin P-3 Biological Activity

Description Ansamitocin P-3 is a microtubule inhibitor. Ansamitocin P-3 is a macrocyclic antitumor antibiotic.
Related Catalog
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
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
OQ2291000
CHEMICAL NAME :
Maytansine, 2'-de(acetylmethylamino)-2'-methyl-
CAS REGISTRY NUMBER :
66584-72-3
LAST UPDATED :
199401
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C32-H43-Cl-N2-O9
MOLECULAR WEIGHT :
635.22

HEALTH HAZARD DATA

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

 Safety Information

Symbol GHS07
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
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