Ansamitocin P-3
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MedKoo CAT#: 123124

CAS#: 66584-72-3 (AP-3)

Description: Ansamitocin P-3 (AP-3) is an active and potent anti-tumor maytansinoid which is usually produced by Actinosynnema spp. Ansamitocin P-3 has shown potent cytotoxicity against the human solid tumor cell lines A-549 and HT-29. Ansamitocin P-3 is useful in synthesizing the anticancer drugs mertansine and emtansine.


Chemical Structure

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Ansamitocin P-3
CAS# 66584-72-3 (AP-3)

Theoretical Analysis

MedKoo Cat#: 123124
Name: Ansamitocin P-3
CAS#: 66584-72-3 (AP-3)
Chemical Formula: C32H43ClN2O9
Exact Mass: 634.26571
Molecular Weight: 635.15
Elemental Analysis: C, 60.51; H, 6.82; Cl, 5.58; N, 4.41; O, 22.67

Size Price Shipping out time Quantity
10mg USD 130 Same Day
25mg USD 250 Same Day
50mg USD 450 Same Day
100mg USD 750 Same Day
200mg USD 1250 Same Day
500mg USD 2150 Same Day
1g USD 3250 Same Day
2g USD 5650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-02-28. Prices are subject to change without notice.

Ansamitocin P-3, purity > 90%, is in stock. The same day shipping out after order is received.

Related CAS #: 66547-09-9 (AP-3')   66584-72-3 (AP-3)    

Synonym: NSC292222; NSC 292222; NSC-292222; Ansamitocin P-3; Maytansinol isobutyrate, Maytansinoid AP-3.

IUPAC/Chemical Name: (14S,16S,32S,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-JBHFWYGFSA-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: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)C(C)C)C)\C)OC)(NC(=O)O2)O

Appearance:
White to off-white solidw powder

Purity:
>90% (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, not in water

Shelf Life:
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 635.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: 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. PubMed PMID: 25564203.

2: 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. PubMed PMID: 25456055.

3: 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. PubMed PMID: 24174216.

4: Segraves NL, Yazzie D, Deese AJ. An isolable acyclic hemiacetal of ansamitocin P-3. Magn Reson Chem. 2012 Mar;50(3):256-9. doi: 10.1002/mrc.2876. Epub 2012 Feb 28. PubMed PMID: 22374862.

5: Jia Y, Zhong JJ. Enhanced production of ansamitocin P-3 by addition of Mg2+ in fermentation of Actinosynnema pretiosum. Bioresour Technol. 2011 Nov;102(21):10147-50. doi: 10.1016/j.biortech.2011.08.031. Epub 2011 Aug 22. PubMed PMID: 21907573.

6: Lin J, Bai L, Deng Z, Zhong JJ. Enhanced production of ansamitocin P-3 by addition of isobutanol in fermentation of Actinosynnema pretiosum. Bioresour Technol. 2011 Jan;102(2):1863-8. doi: 10.1016/j.biortech.2010.09.102. Epub 2010 Oct 25. PubMed PMID: 20980145.

7: Yao Y, Cheng Z, Ye H, Xie Y, He J, Tang M, Shen T, Wang J, Zhou Y, Lu Z, Luo F, Chen L, Yu L, Yang JL, Peng A, Wei Y. Preparative isolation and purification of anti-tumor agent ansamitocin P-3 from fermentation broth of Actinosynnema pretiosum using high-performance counter-current chromatography. J Sep Sci. 2010 May;33(9):1331-7. doi: 10.1002/jssc.200900746. PubMed PMID: 20235129.

8: Liu Z, Floss HG, Cassady JM, Chan KK. Metabolism studies of the anti-tumor agent maytansine and its analog ansamitocin P-3 using liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 2005 Mar;40(3):389-99. PubMed PMID: 15674857.

9: Liu Z, Floss HG, Cassady JM, Xiao J, Chan KK. An API LC/MS/MS quantitation method for ansamitocin P-3 (AP3) and its preclinical pharmacokinetics. J Pharm Biomed Anal. 2004 Nov 19;36(4):815-21. PubMed PMID: 15533675.

10: Li Y, Kobayashi H, Hashimoto Y, Iwasaki S. Binding selectivity of rhizoxin, phomopsin A, vinblastine, and ansamitocin P-3 to fungal tubulins: differential interactions of these antimitotic agents with brain and fungal tubulins. Biochem Biophys Res Commun. 1992 Sep 16;187(2):722-9. Erratum in: Biochem Biophys Res Commun 1993 Feb 15;190(3):1180. PubMed PMID: 1530630.

11: Suwanborirux K, Chang CJ, Spjut RW, Cassady JM. Ansamitocin P-3, a maytansinoid, from Claopodium crispifolium and Anomodon attenuatus or associated actinomycetes. Experientia. 1990 Jan 15;46(1):117-20. PubMed PMID: 2298279.

12: Izawa M, Wada Y, Kasahara F, Asai M, Kishi T. Hydroxylation of ansamitocin P-3. J Antibiot (Tokyo). 1981 Dec;34(12):1591-5. PubMed PMID: 7333973.