N-Me-L-Ala-maytansinol
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MedKoo CAT#: 408084

CAS#: 77668-69-0

Description: N-​Me-​L-​Ala-​maytansinol is a maytansine derivative. .N-​Me-​L-​Ala-​maytansinol can be used for synthesis of antibody-drug conjugate (ADC).


Price and Availability

Size Price Shipping out time Quantity
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2650 2 Weeks
1g USD 3450 2 Weeks
2g USD 5950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

N-Me-L-Ala-maytansinol is in stock.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 408084
Name: N-Me-L-Ala-maytansinol
CAS#: 77668-69-0
Chemical Formula: C32H44ClN3O9
Exact Mass: 649.2766
Molecular Weight: 650.166
Elemental Analysis: C, 59.12; H, 6.82; Cl, 5.45; N, 6.46; O, 22.15


Synonym: N-Me-L-Ala-maytansinol; Maytansinol-Ala;

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 methyl-L-alaninate

InChi Key: ANHBJISROJTYCJ-MSKZWLSNSA-N

InChi Code: InChI=1S/C32H44ClN3O9/c1-17-10-9-11-24(42-8)32(40)16-23(43-30(39)35-32)18(2)28-31(4,45-28)25(44-29(38)19(3)34-5)15-26(37)36(6)21-13-20(12-17)14-22(41-7)27(21)33/h9-11,13-14,18-19,23-25,28,34,40H,12,15-16H2,1-8H3,(H,35,39)/b11-9+,17-10+/t18-,19+,23+,24-,25+,28+,31+,32+/m1/s1

SMILES Code: C[C@]12[C@H]([C@@H]([C@](O3)([H])C[C@]([C@](/C=C/C=C(C)/CC4=CC(N(C)C(C[C@]2([H])OC([C@H](C)NC)=O)=O)=C(C(OC)=C4)Cl)([H])OC)(NC3=O)O)C)O1


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: He J, Yu SF, Yee S, Kaur S, Xu K. Characterization of in vivo biotransformations for trastuzumab emtansine by high-resolution accurate-mass mass spectrometry. MAbs. 2018 Oct;10(7):960-967. doi: 10.1080/19420862.2018.1494487. Epub 2018 Jul 26. PMID: 29958059; PMCID: PMC6204834.

2: 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. PMID: 27102688; PMCID: PMC4840490.

3: 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. PMID: 26572523.

4: 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. PMID: 25467246.

5: 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(1):1473-9. doi: 10.2119/molmed.2012.00302. PMID: 23196784; PMCID: PMC3563710.

6: 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. PMID: 23061718.

7: 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. PMID: 22374862.

8: 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. PMID: 21504911; PMCID: PMC3124055.

9: 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. PMID: 20582809.

10: 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. doi: 10.1021/ja020214b. PMID: 12047169.

11: Bénéchie M, Khuong-Huu F. Total Synthesis of (-)-Maytansinol. J Org Chem. 1996 Oct 4;61(20):7133-7138. doi: 10.1021/jo960363a. PMID: 11667616.

12: 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. doi: 10.1021/bc00022a006. PMID: 8218485.

13: 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. PMID: 6441645.

14: Nakahama K, Izawa M, Asai M, Kida M, Kishi T. Microbial conversion of ansamitocin. J Antibiot (Tokyo). 1981 Dec;34(12):1581-6. doi: 10.7164/antibiotics.34.1581. PMID: 7333971.

15: Ikeyama S, Takeuchi M. Antitubulin activities of ansamitocins and maytansinoids. Biochem Pharmacol. 1981 Sep 1;30(17):2421-5. doi: 10.1016/0006-2952(81)90336-1. PMID: 21043240.

16: 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. doi: 10.1021/jm00199a006. PMID: 563462.

17: 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. doi: 10.1021/ja00851a054. PMID: 1165364.