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.

Chemical Structure

CAS# 400647-59-8

Theoretical Analysis

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

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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 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

Appearance: Red 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, not in water

Shelf Life: >2 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

Preparing Stock Solutions

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.

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

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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

Additional Information