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MedKoo Cat#: 408084 | Name: N-Me-L-Ala-maytansinol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

N-Me-L-Ala-maytansinol
N-Me-L-Ala-maytansinol
CAS#77668-69-0

Theoretical Analysis

MedKoo Cat#: 408084

Name: N-Me-L-Ala-maytansinol

CAS#: 77668-69-0

Chemical Formula: C32H44ClN3O9

Exact Mass: 649.2766

Molecular Weight: 650.17

Elemental Analysis: C, 59.12; H, 6.82; Cl, 5.45; N, 6.46; O, 22.15

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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
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
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 650.17 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.

Recalculate based on batch purity %
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
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.

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