An ansa macrolide
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Maytansinol

Item No. 29228

Technical Information
Formal Name
3-O-de[2-(acetylmethylamino)-1-oxopropyl]-maytansine
CAS Number
57103-68-1
Synonyms
  • Ansamitocin P-0
  • Antibiotic C-15003P0
  • NSC 239386
Molecular Formula
C28H37ClN2O8
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 25 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): Partially soluble
λmax
232, 244, 253 nm
SMILES
ClC1=C(N2C)C=C(C/C(C)=C/C=C/[C@@H](OC)[C@]3(O)NC(O[C@@]([C@@H](C)[C@@](O4)([H])[C@]4(C)[C@@H](O)CC2=O)([H])C3)=O)C=C1OC
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
InChi Key
QWPXBEHQFHACTK-RZKXNLMUSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Maytansinol is an ansa macrolide originally isolated from P. verrucose that has antimitotic and anticancer activities.1,2,3 It inhibits polymerization and induces depolymerization of bovine brain tubulin with EC50 values of 12 and 43 µM, respectively.2 Maytansinol inhibits sea urchin egg mitosis when used at a concentration of 10 µM and decreases proliferation of KB nasopharyngeal cancer cells (EC50 = 0.19 µg/ml).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kupchan, S.M., Branfman, A.R., Sneden, A.T., et alNovel maytansinoids. Naturally occurring and synthetic antileukemic esters of maytansinol. J. Am. Chem. Soc. 97(18), 5294-5295 (1975).

    2. Ikeyama, S., and Takeuchi, M. Antitubulin activities of ansamitocins and maytansinoids. Biochem. Pharmacol. 30(17), 2421-2425 (1981).

    3. Kupchan, S.M., Sneden, A.T., Branfman, A.R., et alStructural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoids. J. Med. Chem. 21(1), 31-37 (1978).