Ansamitocin P3
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MedKoo CAT#: 408085

CAS#: 66584-72-3

Description: Ansamitocin P-3 is a natural product isolated from Actinosynnema pretiosum. Ansamitocin P3 is a fungal metabolite with antineoplastic, antimitotic activity. Ansamitocin P3 binds to tubulin and inhibits vinblastine-induced spiral formation.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 1950 2 Weeks
1g USD 2950 2 Weeks
2g USD 5250 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-06-07. Prices are subject to change without notice.

Ansamitocin P3 is in stock


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 408085
Name: Ansamitocin P3
CAS#: 66584-72-3
Chemical Formula: C32H43ClN2O9
Exact Mass: 634.2657
Molecular Weight: 635.151
Elemental Analysis: C, 60.51; H, 6.82; Cl, 5.58; N, 4.41; O, 22.67


Synonym: Ansamitocin P3; AP-3;

IUPAC/Chemical Name: (14S,16S,32R,33S,2R,4S,10E,12E,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl isobutyrate

InChi Key: OPQNCARIZFLNLF-KUDLRRJMSA-N

InChi Code: InChI=1S/C32H43ClN2O9/c1-17(2)29(37)43-25-15-26(36)35(6)21-13-20(14-22(40-7)27(21)33)12-18(3)10-9-11-24(41-8)32(39)16-23(42-30(38)34-32)19(4)28-31(25,5)44-28/h9-11,13-14,17,19,23-25,28,39H,12,15-16H2,1-8H3,(H,34,38)/b11-9+,18-10+/t19-,23+,24-,25+,28-,31+,32+/m1/s1

SMILES Code: CO[C@@H]1/C=C/C=C(CC2=CC(OC)=C(C(N(C(C[C@@H]([C@@]3(O[C@@H]3[C@@H]([C@@H]4C[C@]1(NC(O4)=O)O)C)C)OC(C(C)C)=O)=O)C)=C2)Cl)\C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Liu T, Jin Z, Wang Z, Chen J, Wei LJ, Hua Q. Metabolomics analysis of Actinosynnema pretiosum with improved AP-3 production by enhancing UDP-glucose biosynthesis. J Biosci Bioeng. 2020 Mar 13:S1389-1723(19)30878-3. doi: 10.1016/j.jbiosc.2020.02.013. Epub ahead of print. PMID: 32179024.

2: Liu T, Yang L, Chen J, Hu F, Wei LJ, Hua Q. Metabolomic change and pathway profiling reveal enhanced ansamitocin P-3 production in Actinosynnema pretiosum with low organic nitrogen availability in culture medium. Appl Microbiol Biotechnol. 2020 Apr;104(8):3555-3568. doi: 10.1007/s00253-020-10463-9. Epub 2020 Feb 29. PMID: 32114676.

3: Kashyap AS, Fernandez-Rodriguez L, Zhao Y, Monaco G, Trefny MP, Yoshida N, Martin K, Sharma A, Olieric N, Shah P, Stanczak M, Kirchhammer N, Park SM, Wieckowski S, Laubli H, Zagani R, Kasenda B, Steinmetz MO, Reinecker HC, Zippelius A. GEF-H1 Signaling upon Microtubule Destabilization Is Required for Dendritic Cell Activation and Specific Anti-tumor Responses. Cell Rep. 2019 Sep 24;28(13):3367-3380.e8. doi: 10.1016/j.celrep.2019.08.057. PMID: 31553907; PMCID: PMC6876861.

4: Du ZQ, Zhang Y, Qian ZG, Xiao H, Zhong JJ. Erratum for "Combination of traditional mutation and metabolic engineering to enhance ansamitocin P-3 production in Actinosynnema pretiosum" (Vol. 114, Issue 12, pp. 2794-2806). Biotechnol Bioeng. 2018 Oct;115(10):2668. doi: 10.1002/bit.26796. Epub 2018 Aug 8. Erratum for: Biotechnol Bioeng. 2017 Dec;114(12):2794-2806. PMID: 30311648.

5: Li J, Sun R, Ning X, Wang X, Wang Z. Genome-Scale Metabolic Model of Actinosynnema pretiosum ATCC 31280 and Its Application for Ansamitocin P-3 Production Improvement. Genes (Basel). 2018 Jul 20;9(7):364. doi: 10.3390/genes9070364. PMID: 30036981; PMCID: PMC6070911.

6: Du ZQ, Zhong JJ. Rational approach to improve ansamitocin P-3 production by integrating pathway engineering and substrate feeding in Actinosynnema pretiosum. Biotechnol Bioeng. 2018 Oct;115(10):2456-2466. doi: 10.1002/bit.26775. Epub 2018 Jul 20. PMID: 29940067.

7: Zhong C, Zong G, Qian S, Liu M, Fu J, Zhang P, Li J, Cao G. Complete Genome Sequence of Actinosynnema pretiosum X47, An Industrial Strain that Produces the Antibiotic Ansamitocin AP-3. Curr Microbiol. 2019 Aug;76(8):954-958. doi: 10.1007/s00284-018-1521-1. Epub 2018 Jun 1. PMID: 29858620.

8: Ning X, Wang X, Wu Y, Kang Q, Bai L. Identification and Engineering of Post- PKS Modification Bottlenecks for Ansamitocin P-3 Titer Improvement in Actinosynnema pretiosum subsp. pretiosum ATCC 31280. Biotechnol J. 2017 Nov;12(11). doi: 10.1002/biot.201700484. Epub 2017 Sep 25. PMID: 28881098.

9: Du ZQ, Zhang Y, Qian ZG, Xiao H, Zhong JJ. Combination of traditional mutation and metabolic engineering to enhance ansamitocin P-3 production in Actinosynnema pretiosum. Biotechnol Bioeng. 2017 Dec;114(12):2794-2806. doi: 10.1002/bit.26396. Epub 2017 Aug 23. Erratum in: Biotechnol Bioeng. 2018 Oct;115(10):2668. PMID: 28782796.

10: Lin J, Zhong JJ. Proteomic studies on anti-tumor agent ansamitocin P-3 producer Actinosynnema pretiosum in response to ammonium and isobutanol. Bioprocess Biosyst Eng. 2017 Jul;40(7):1133-1139. doi: 10.1007/s00449-017-1763-5. Epub 2017 Apr 5. PMID: 28382459.

11: Zhao M, Fan Y, Wei L, Hu F, Hua Q. Effects of the Methylmalonyl-CoA Metabolic Pathway on Ansamitocin Production in Actinosynnema pretiosum. Appl Biochem Biotechnol. 2017 Mar;181(3):1167-1178. doi: 10.1007/s12010-016-2276-4. Epub 2016 Oct 27. PMID: 27787765.

12: Fan Y, Hu F, Wei L, Bai L, Hua Q. Effects of modulation of pentose-phosphate pathway on biosynthesis of ansamitocins in Actinosynnema pretiosum. J Biotechnol. 2016 Jul 20;230:3-10. doi: 10.1016/j.jbiotec.2016.05.010. Epub 2016 May 9. PMID: 27173582.

13: Fan Y, Zhao M, Wei L, Hu F, Imanaka T, Bai L, Hua Q. Enhancement of UDPG synthetic pathway improves ansamitocin production in Actinosynnem pretiosum. Appl Microbiol Biotechnol. 2016 Mar;100(6):2651-62. doi: 10.1007/s00253-015-7148-2. Epub 2015 Nov 19. PMID: 26585444.

14: Zhang YG, Liu Q, Wang HF, Park DJ, Guo JW, Kim CJ, Zhang YM, Li WJ. Nocardiopsis ansamitocini sp. nov., a new producer of ansamitocin P-3 of the genus Nocardiopsis. Int J Syst Evol Microbiol. 2016 Jan;66(1):230-235. doi: 10.1099/ijsem.0.000703. Epub 2015 Oct 20. PMID: 26486850.

15: Li T, Fan Y, Nambou K, Hu F, Imanaka T, Wei L, Hua Q. Improvement of ansamitocin P-3 production by Actinosynnema mirum with fructose as the sole carbon source. Appl Biochem Biotechnol. 2015 Mar;175(6):2845-56. doi: 10.1007/s12010-014-1445-6. Epub 2015 Jan 7. PMID: 25564203.

16: Fan Y, Gao Y, Zhou J, Wei L, Chen J, Hua Q. Process optimization with alternative carbon sources and modulation of secondary metabolism for enhanced ansamitocin P-3 production in Actinosynnema pretiosum. J Biotechnol. 2014 Dec 20;192 Pt A:1-10. doi: 10.1016/j.jbiotec.2014.10.020. PMID: 25456055.

17: Müller P, Martin K, Theurich S, von Bergwelt-Baildon M, Zippelius A. Cancer chemotherapy agents target intratumoral dendritic cells to potentiate antitumor immunity. Oncoimmunology. 2014 Aug 3;3(8):e954460. doi: 10.4161/21624011.2014.954460. PMID: 25610745; PMCID: PMC4292760.

18: Martin K, Müller P, Schreiner J, Prince SS, Lardinois D, Heinzelmann-Schwarz VA, Thommen DS, Zippelius A. The microtubule-depolymerizing agent ansamitocin P3 programs dendritic cells toward enhanced anti-tumor immunity. Cancer Immunol Immunother. 2014 Sep;63(9):925-38. doi: 10.1007/s00262-014-1565-4. Epub 2014 Jun 7. PMID: 24906866.

19: Gao Y, Fan Y, Nambou K, Wei L, Liu Z, Imanaka T, Hua Q. Enhancement of ansamitocin P-3 production in Actinosynnema pretiosum by a synergistic effect of glycerol and glucose. J Ind Microbiol Biotechnol. 2014 Jan;41(1):143-52. doi: 10.1007/s10295-013-1374-3. Epub 2013 Oct 31. PMID: 24174216.

20: Venghateri JB, Gupta TK, Verma PJ, Kunwar A, Panda D. Ansamitocin P3 depolymerizes microtubules and induces apoptosis by binding to tubulin at the vinblastine site. PLoS One. 2013 Oct 4;8(10):e75182. doi: 10.1371/journal.pone.0075182. PMID: 24124473; PMCID: PMC3790769.