Top Clicks This Month

Not Intended for Therapeutic Use. For research use only.

Maytansinol - CAS 57103-68-1

Quick Inquiry

Name:
* Email:
* Service & Products of Interest:
* Quantity:
* Verification code:
Please input "bocsci" as verification code.
Category
ADCs
Product Name
Maytansinol
Catalog Number
57103-68-1
Synonyms
MAYTANSINOL; 57103-68-1; NSC239386; NSC-239386; Maytansine; Ansamitocin P 0; Antibiotic C 15003P
CAS Number
57103-68-1
Description
The maytansinol, also called Ansamitocin P 0, Maytansine,ect, is useful for preparing cell-binding/maytansinoid agent complexes. Maytansinol can be prepared by LiAlH4 treatment of maytanbutine in dry THF at -23º for 3 hr (40% yield). And the naturally occurring and synthetic C-3 esters of maytansinol can be classified into two groups:Maytansine and its analogs.Maytanacine and maytansinol propionate have strong anti-tumor activity.On the other hand, maytansinol itself has only weak anti-tumor activity.
Molecular Weight
565.05
Molecular Formula
C28H37ClN2O8
Quantity
Grams-Kilos
Quality Standard
In-house Standard
COA
Certificate of Analysis-Maytansinol 57103-68-1 B16W05181  
MSDS
Inquire
Canonical SMILES
CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)O)C)C)OC)(NC(=O)O2)O
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+
InChIKey
QWPXBEHQFHACTK-KAIGDTDQSA-N
Size Price Stock Quantity
100 mg $479 In stock
200 mg $899 In stock

Bulk Inquiry

Name:
* Email:
* Service & Products of Interest:
* Quantity:
* Verification code:
Please input "bocsci" as verification code.
Structure
CAS 57103-68-1 Maytansinol
Specification
Purity
≥ 95.0%
Melting Point
205-207ºC
Appearance
Light yellow powder
Application
A useful intermediate for easy preparation of maytanacine and maytansinol propionate and other various derivatives;Inhibits microtubule assembly and induces microtubule disassembly in vitro; Exhibits cytotoxicity against many tumor cell lines and inhibits tumor growth in vivo; Antileukemic ansa macrolide
Storage
Store at 2-8ºC
Solubility
Sparingly Soluble (2.2E-3 g/L) (25 ºC), Calc.*
Related Products
Reference Reading
1. Modification of post-PKS tailoring steps through combinatorial biosynthesis
Uwe Rix, Carsten Fischer, Lily L. Remsing, Jürgen Rohr *. Nat. Prod. Rep., 2002, 19, 542–580
Epp et al. were able to show that recombination of CarE with either the spiromycin producer S. ambofaciens or S. lividans (exogenously fed spiromycin was necessary) resulted in the formation of the hybrid compound isovaleryl spiromycin. Recently, the acyltransferase encoding gene asm19 from the gene cluster of the ansa-macrolactam maytansine has been identified through sequence analysis and in-frame deletion. Surprisingly, the corresponding enzyme Asm19 attaches the biologically essential ester side chain of the ansamitocins using N-demethyl-4,5-desepoxymaytansinol as its substrate, and not maytansinol, as was generally believed. Thus, this acyl-transferase acts on a much earlier stage of the maytansin biosynthetic pathway than expected.
2. Total synthesis approaches to natural product derivatives based on the combination of chemical synthesis and metabolic engineering
Andreas Kirschning,* Florian Taft, Tobias Knobloch. Org. Biomol. Chem., 2007, 5, 3245–3259
In principle, the selective expression of late-stage enzymes can be employed for the engineered production of intermediates with desired functionalities suitable for further chemical modification and detailed SAR studies. However, intermediates partially lacking peripheral decorations are often accumulated in lower yields than their fully modified counterparts. Furthermore, omittance of a specific modification in the biosynthetic assembly logicmight interfere with the substrate specificities of downstream core-decorating enzymes, thus not leading to the accumulation of the desired compound, but to partiallymodified intermediates.For instance, the inactivation of the acyltransferase in the ansamitocin pathway of Actinosynnema pretiosum did not lead to the expected maytansinol, but to its N-demethyl-desepoxy analogue.
3. Industrial natural product chemistry for drug discovery and development
Armin Bauer*, Mark Bronstrup*. Nat. Prod. Rep.,2014, 31,35–60
As also observed for other tubulin-binding anti-cancer agents, this interaction led to arrest in the G2-M phase of the cell cycle and subsequently to apoptosis. Early clinical trials with 65 were initiated in the 1970s. However, dose-limiting toxicity and lack of response in the majority of patients enrolled in phase II trials led to the discontinuation of 65 as a single agent for anti-cancer therapy. From the early 1990s on, the maytansinoids were re-investigated for their use as toxic payloads for antibodies. 66 was chosen as the starting material for semisynthesis, since it was readily available from fermentation. DM1 68 and other relatedmaytansinoids suitable for conjugation (such as DM4 69) were synthesized from may- tansinol 67, which is obtained by reductive cleavage of 66 at the acyloxy function at C3 with LiAlH(OMe)3. Re-esterification of maytansinol with several carboxylic acids mediated by DCC/ZnCl2 led to new derivatives displaying cytotoxic activity in the 10–90 pMrange, which corresponded to an ideal potency for the use as toxic payloads in antibody conjugates.
2005 - BOC Sciences | All rights reserved
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE
BOCSciences
X CLOSE