WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406622
CAS#: 400647-59-8
Description: Doxorubicin-SMCC, also known as ADR-SMCC, dox-SMCC, is a derivative of doxorubicin with a SMCC linker (Succinimidyl-4-( N -maleimidomethyl)cyclohexane-1-carboxylate). Maleimide in doxrubicin-SMCC can react with sulfhydryl groups at pH 6.5-7.5 to form a stable thioether bond. Doxorubicin-SMCC can be used to synthesize doxorubicin bioconjugates with proteins, enzymes; antobodies, antigens, and other biopolymers. Doxorubicin-SMCC is often used for drug delivery research.
MedKoo Cat#: 406622
Name: Doxorubicin-SMCC
CAS#: 400647-59-8
Chemical Formula: C39H42N2O14
Exact Mass: 762.2636
Molecular Weight: 762.76
Elemental Analysis: C, 61.41; H, 5.55; N, 3.67; O, 29.37
Doxorubicin-SMCC, purity > 98%, is in stock. The same day shipping out after order is received.
Synonym: Doxorubicin-SMCC; ADR-SMCC; Dox-SMCC Doxo-SMCC.
IUPAC/Chemical Name: 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)-N-((2S,3S,4S,6R)-3-hydroxy-2-methyl-6-(((1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl)oxy)tetrahydro-2H-pyran-4-yl)cyclohexanecarboxamide
InChi Key: OTQOQHVWNBKSGU-SAJDXUNTSA-N
InChi Code: InChI=1S/C39H42N2O14/c1-17-33(46)22(40-38(51)19-8-6-18(7-9-19)15-41-26(44)10-11-27(41)45)12-28(54-17)55-24-14-39(52,25(43)16-42)13-21-30(24)37(50)32-31(35(21)48)34(47)20-4-3-5-23(53-2)29(20)36(32)49/h3-5,10-11,17-19,22,24,28,33,42,46,48,50,52H,6-9,12-16H2,1-2H3,(H,40,51)/t17-,18?,19?,22-,24-,28-,33+,39-/m0/s1
SMILES Code: C[C@@H]1O[C@@H](O[C@@H](C2)C3=C(O)C(C4=O)=C(C(C5=C4C(OC)=CC=C5)=O)C(O)=C3C[C@@]2(O)C(CO)=O)C[C@H](NC(C6CCC(CN7C(C=CC7=O)=O)CC6)=O)[C@@H]1O
The following data is based on the product molecular weight 762.76 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.
| 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. Chen, Q.; Gabathuler, R., Efficient Synthesis of Doxorubicin Melanotransferrin p97 Conjugates Through SMCC Linker. Synth. Commun. 2004, 34, (13), 2407-2414.
2: A Flow Cytometric Clonogenic Assay Reveals the Single-Cell Potency of Doxorubicin Katie F. Maass, Chethana Kulkarni, Mohiuddin A. Quadir, Paula T. Hammond, Alison M. Betts, K. Dane Wittrup J Pharm Sci. Author manuscript; available in PMC 2016 Dec 1.Published in final edited form as: J Pharm Sci. 2015 Dec; 104(12): 4409–4416. Published online 2015 Sep 7. doi: 10.1002/jps.24631 PMCID: PMC4706798
