DM1-SMe is a potent maytansinoid microtubular inhibitor and an unconjugated DM1 as a mixed disulfide with thiomethane to cap its sulfhydryl group. To create an antibody-drug conjugate (ADC), DM1-SMe is easily conjugated to an antibody's SH group.
Physicochemical Properties
| Molecular Formula | C36H50CLN3O10S2 |
| Molecular Weight | 784.377 |
| Exact Mass | 783.263 |
| Elemental Analysis | C, 55.13; H, 6.43; Cl, 4.52; N, 5.36; O, 20.40; S, 8.17 |
| CAS # | 138148-68-2 |
| Related CAS # | 138148-68-2 |
| PubChem CID | 11650734 |
| Appearance | White to off-white solid powder |
| LogP | 5.309 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 52 |
| Complexity | 1370 |
| Defined Atom Stereocenter Count | 8 |
| SMILES | CSSCCC(N(C)[C@@H](C)C(O[C@@H]1[C@@]2(O[C@H]2[C@H](C)[C@H]2OC(N[C@](O)(C2)[C@H](OC)C=CC=C(C)CC2C=C(OC)C(Cl)=C(C=2)N(C)C(=O)C1)=O)C)=O)=O |t:30,32,37,&1:8,12,13,15,16,18,22,25| |
| InChi Key | ZLUUPZXOPGORNG-UDXCHANISA-N |
| InChi Code | InChI=1S/C36H50ClN3O10S2/c1-20-11-10-12-27(47-8)36(45)19-26(48-34(44)38-36)21(2)32-35(4,50-32)28(49-33(43)22(3)39(5)29(41)13-14-52-51-9)18-30(42)40(6)24-16-23(15-20)17-25(46-7)31(24)37/h10-12,16-17,21-22,26-28,32,45H,13-15,18-19H2,1-9H3,(H,38,44)/b12-10-,20-11-/t21-,22+,26+,27-,28+,32+,35+,36+/m1/s1 |
| Chemical Name | [(1S,2R,3S,5S,6S,16Z,18Z,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[methyl-[3-(methyldisulfanyl)propanoyl]amino]propanoate |
| Synonyms | DM1-SMe; SMe-DM4; mDM1-SSMe; Maytansine or mertansine or emtansine derivative; aytansinoid derivative with ADC linker; N2'-deacetyl-N2'-[3-(methyldithio)-1-oxopropyl]maytansine. |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Maytansinoids |
| References |
[1]. Initial testing (Stage 1) of the antibody-maytansinoid conjugate, IMGN901 (Lorvotuzumab mertansine), by the pediatric preclinical testing program. Pediatr Blood Cancer. 2013;60(11):1860-1867. [2]. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res. 2008;41(1):98-107. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~100 mg/mL (~127.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2749 mL | 6.3745 mL | 12.7489 mL | |
| 5 mM | 0.2550 mL | 1.2749 mL | 2.5498 mL | |
| 10 mM | 0.1275 mL | 0.6374 mL | 1.2749 mL |