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MedKoo Cat#: 406622 | Name: Doxorubicin-SMCC
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Doxorubicin-SMCC
Doxorubicin-SMCC
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

Price and Availability

Size Price Availability Quantity
1mg USD 90.00 Ready to ship
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 550.00 Ready to ship
50mg USD 950.00 Ready to ship
100mg USD 1,650.00 Ready to ship
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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 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
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
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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
1: Rivankar S. An overview of doxorubicin formulations in cancer therapy. J Cancer Res Ther. 2014 Oct-Dec;10(4):853-8. doi: 10.4103/0973-1482.139267. PMID: 25579518. 2: Speth PA, van Hoesel QG, Haanen C. Clinical pharmacokinetics of doxorubicin. Clin Pharmacokinet. 1988 Jul;15(1):15-31. doi: 10.2165/00003088-198815010-00002. PMID: 3042244. 3: Carvalho C, Santos RX, Cardoso S, Correia S, Oliveira PJ, Santos MS, Moreira PI. Doxorubicin: the good, the bad and the ugly effect. Curr Med Chem. 2009;16(25):3267-85. doi: 10.2174/092986709788803312. Epub 2009 Sep 1. PMID: 19548866. 4: Zhu L, Lin M. The Synthesis of Nano-Doxorubicin and its Anticancer Effect. Anticancer Agents Med Chem. 2021;21(18):2466-2477. doi: 10.2174/1871520621666201229115612. PMID: 33372884. 5: Peter S, Alven S, Maseko RB, Aderibigbe BA. Doxorubicin-Based Hybrid Compounds as Potential Anticancer Agents: A Review. Molecules. 2022 Jul 13;27(14):4478. doi: 10.3390/molecules27144478. PMID: 35889350; PMCID: PMC9318127. 6: Sun Z, Zhou D, Yang J, Zhang D. Doxorubicin promotes breast cancer cell migration and invasion via DCAF13. FEBS Open Bio. 2022 Jan;12(1):221-230. doi: 10.1002/2211-5463.13330. Epub 2021 Dec 5. PMID: 34775691; PMCID: PMC8727929. 7: Meredith AM, Dass CR. Increasing role of the cancer chemotherapeutic doxorubicin in cellular metabolism. J Pharm Pharmacol. 2016 Jun;68(6):729-41. doi: 10.1111/jphp.12539. Epub 2016 Mar 14. PMID: 26989862. 8: Almajidi YQ, Kadhim MM, Alsaikhan F, Turki Jalil A, Hassan Sayyid N, Alexis Ramírez-Coronel A, Hassan Jawhar Z, Gupta J, Nabavi N, Yu W, Ertas YN. Doxorubicin-loaded micelles in tumor cell-specific chemotherapy. Environ Res. 2023 Jun 15;227:115722. doi: 10.1016/j.envres.2023.115722. Epub 2023 Mar 21. PMID: 36948284. 9: Tardi PG, Boman NL, Cullis PR. Liposomal doxorubicin. J Drug Target. 1996;4(3):129-40. doi: 10.3109/10611869609015970. PMID: 8959485. 10: Armstrong J, Dass CR. Doxorubicin Action on Mitochondria: Relevance to Osteosarcoma Therapy? Curr Drug Targets. 2018;19(5):432-438. doi: 10.2174/1389450116666150416115852. PMID: 25882220. 11: Schulmeister L. Doxorubicin. Clin J Oncol Nurs. 1998 Jul;2(3):115-6. PMID: 10232157. 12: Alam Khan S, Jawaid Akhtar M. Structural modification and strategies for the enhanced doxorubicin drug delivery. Bioorg Chem. 2022 Mar;120:105599. doi: 10.1016/j.bioorg.2022.105599. Epub 2022 Jan 7. PMID: 35030480. 13: Tan ML, Choong PF, Dass CR. Review: doxorubicin delivery systems based on chitosan for cancer therapy. J Pharm Pharmacol. 2009 Feb;61(2):131-42. doi: 10.1211/jpp/61.02.0001. PMID: 19178759. 14: Chlebowski RT. Adriamycin (doxorubicin) cardiotoxicity: a review. West J Med. 1979 Nov;131(5):364-8. PMID: 394479; PMCID: PMC1271861. 15: Lum BL, Svec JM, Torti FM. Doxorubicin: alteration of dose scheduling as a means of reducing cardiotoxicity. Drug Intell Clin Pharm. 1985 Apr;19(4):259-64. doi: 10.1177/106002808501900403. PMID: 3891276. 16: Bielack SS, Erttmann R, Winkler K, Landbeck G. Doxorubicin: effect of different schedules on toxicity and anti-tumor efficacy. Eur J Cancer Clin Oncol. 1989 May;25(5):873-82. doi: 10.1016/0277-5379(89)90135-1. PMID: 2661240. 17: Cuono CB. Doxorubicin-induced extravasation necrosis. J Hand Surg Am. 1983 Jul;8(4):497-8. doi: 10.1016/s0363-5023(83)80216-0. PMID: 6886347. 18: Alawak M, Dayyih AA, Awak I, Gutberlet B, Engelhardt K, Bakowsky U. Magnetic Thermosensitive Liposomes Loaded with Doxorubicin. Methods Mol Biol. 2023;2622:103-119. doi: 10.1007/978-1-0716-2954-3_9. PMID: 36781754. 19: Tian Z, Yang Y, Yang Y, Zhang F, Li P, Wang J, Yang J, Zhang P, Yao W, Wang X. High cumulative doxorubicin dose for advanced soft tissue sarcoma. BMC Cancer. 2020 Nov 23;20(1):1139. doi: 10.1186/s12885-020-07663-x. PMID: 33228579; PMCID: PMC7684756. 20: Gong J, Yan J, Forscher C, Hendifar A. Aldoxorubicin: a tumor-targeted doxorubicin conjugate for relapsed or refractory soft tissue sarcomas. Drug Des Devel Ther. 2018 Apr 6;12:777-786. doi: 10.2147/DDDT.S140638. PMID: 29670334; PMCID: PMC5896668.