Maytansinol
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MedKoo CAT#: 407810

CAS#: 57103-68-1

Description: Maytansinol, also known as Ansamitocin P-0, is a potent microtubule depolymerizing agent. Maytansinol inhibits microtubule assembly and induces microtubule disassembly in vitro. Maytansinol disrupts the mitotic spindle and prevents mitotic exit in Drosophila. Maytansinol is used in the preparation of site-specific trastuzumab maytansinoid antibody-drug conjugates with improved therapeutic activity.


Price and Availability

Size
Price

100mg
USD 950
1g
USD 3850
Size
Price

200mg
USD 1650
2g
USD 5450
Size
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500mg
USD 2650
5g
Ask price

Maytansinol, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407810
Name: Maytansinol
CAS#: 57103-68-1
Chemical Formula: C28H37ClN2O8
Exact Mass: 564.2238
Molecular Weight: 565.06
Elemental Analysis: C, 59.52; H, 6.60; Cl, 6.27; N, 4.96; O, 22.65


Synonym: Maytansinol; Ansamitocin P-0; Antibiotic C 15003P 0; NSC 239386.

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

InChi Key: QWPXBEHQFHACTK-RZKXNLMUSA-N

InChi Code: InChI=1S/C28H37ClN2O8/c1-15-8-7-9-22(37-6)28(35)14-20(38-26(34)30-28)16(2)25-27(3,39-25)21(32)13-23(33)31(4)18-11-17(10-15)12-19(36-5)24(18)29/h7-9,11-12,16,20-22,25,32,35H,10,13-14H2,1-6H3,(H,30,34)/b9-7+,15-8+/t16-,20+,21+,22-,25+,27+,28+/m1/s1

SMILES Code: O=C1O[C@@]([C@@H](C)[C@H]2[C@](C)([C@@H](O)CC3=O)O2)([H])C[C@@]([C@H](OC)/C=C/C=C(CC4=CC(OC)=C(Cl)C(N3C)=C4)\C)(O)N1


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:
>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).

Harmonized System Code:
293490


References

1: Feng L, Yao HP, Zhou YQ, Zhou J, Zhang R, Wang MH. Biological evaluation of antibody-maytansinoid conjugates as a strategy of RON targeted drug delivery for treatment of non-small cell lung cancer. J Exp Clin Cancer Res. 2016 Apr 22;35:70. doi: 10.1186/s13046-016-0347-6. Erratum in: J Exp Clin Cancer Res. 2016;35(1):95. PubMed PMID: 27102688; PubMed Central PMCID: PMC4840490.

2: Li S, Lu C, Chang X, Shen Y. Constitutive overexpression of asm18 increases the production and diversity of maytansinoids in Actinosynnema pretiosum. Appl Microbiol Biotechnol. 2016 Mar;100(6):2641-9. doi: 10.1007/s00253-015-7127-7. Epub 2015 Nov 17. PubMed PMID: 26572523.

3: Mang Y, Zhao Z, Zeng Z, Wu X, Li Z, Zhang L. Efficient elimination of CD103-expressing cells by anti-CD103 antibody drug conjugates in immunocompetent mice. Int Immunopharmacol. 2015 Jan;24(1):119-27. doi: 10.1016/j.intimp.2014.11.004. Epub 2014 Nov 15. PubMed PMID: 25467246.

4: Barginear MF, John V, Budman DR. Trastuzumab-DM1: a clinical update of the novel antibody-drug conjugate for HER2-overexpressing breast cancer. Mol Med. 2013 Jan 22;18:1473-9. doi: 10.2119/molmed.2012.00302. PubMed PMID: 23196784; PubMed Central PMCID: PMC3563710.

5: Siyu-Mao, Hong-Chen, Li-Chen, Chuanxi-Wang, Wei-Jia, Xiaoming-Chen, Huangjian-Yang, Wei-Huang, Wei-Zheng. Two novel ansamitocin analogs from Actinosynnema pretiosum. Nat Prod Res. 2013;27(17):1532-6. doi: 10.1080/14786419.2012.733388. Epub 2012 Oct 15. PubMed PMID: 23061718.

6: 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.

7: Edwards A, Gladstone M, Yoon P, Raben D, Frederick B, Su TT. Combinatorial effect of maytansinol and radiation in Drosophila and human cancer cells. Dis Model Mech. 2011 Jul;4(4):496-503. doi: 10.1242/dmm.006486. Epub 2011 Apr 18. PubMed PMID: 21504911; PubMed Central PMCID: PMC3124055.

8: Wei GZ, Bai LQ, Yang T, Ma J, Zeng Y, Shen YM, Zhao PJ. A new antitumour ansamitocin from Actinosynnema pretiosum. Nat Prod Res. 2010 Jul;24(12):1146-50. doi: 10.1080/14786410902916552. PubMed PMID: 20582809.

9: Moss SJ, Bai L, Toelzer S, Carroll BJ, Mahmud T, Yu TW, Floss HG. Identification of asm19 as an acyltransferase attaching the biologically essential ester side chain of ansamitocins using N-desmethyl-4,5-desepoxymaytansinol, not maytansinol, as its substrate. J Am Chem Soc. 2002 Jun 12;124(23):6544-5. PubMed PMID: 12047169.

10: Bénéchie M, Khuong-Huu F. Total Synthesis of (-)-Maytansinol. J Org Chem. 1996 Oct 4;61(20):7133-7138. PubMed PMID: 11667616.

11: Sawada T, Kato Y, Kobayashi H, Hashimoto Y, Watanabe T, Sugiyama Y, Iwasaki S. A fluorescent probe and a photoaffinity labeling reagent to study the binding site of maytansine and rhizoxin on tubulin. Bioconjug Chem. 1993 Jul-Aug;4(4):284-9. PubMed PMID: 8218485.

12: Kawai A, Akimoto H, Kozai Y, Ootsu K, Tanida S, Hashimoto N, Nomura H. Chemical modification of ansamitocins. III. Synthesis and biological effects of 3-acyl esters of maytansinol. Chem Pharm Bull (Tokyo). 1984 Sep;32(9):3341-51. PubMed PMID: 6441645.

13: Nakahama K, Izawa M, Asai M, Kida M, Kishi T. Microbial conversion of ansamitocin. J Antibiot (Tokyo). 1981 Dec;34(12):1581-6. PubMed PMID: 7333971.

14: Ikeyama S, Takeuchi M. Antitubulin activities of ansamitocins and maytansinoids. Biochem Pharmacol. 1981 Sep 1;30(17):2421-5. PubMed PMID: 21043240.

15: Kupchan SM, Sneden AT, Branfman AR, Howie GA, Rebhun LI, McIvor WE, Wang RW, Schnaitman TC. Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoids. J Med Chem. 1978 Jan;21(1):31-7. PubMed PMID: 563462.

16: Kupchan SM, Branfman AR, Sneden AT, Verma AK, Dailey RG Jr, Komoda Y, Nagao Y. Letter: Novel maytansinoids. Naturally occurring and synthetic antileukemic esters of maytansinol. J Am Chem Soc. 1975 Sep 3;97(18):5294-5. PubMed PMID: 1165364.