Synonym
MC-70; MC 70; MC70.
IUPAC/Chemical Name
4'-((6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-[1,1'-biphenyl]-4-ol
InChi Key
ATYXTVKHMLAWBZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H25NO3/c1-27-23-13-20-11-12-25(16-21(20)14-24(23)28-2)15-17-3-5-18(6-4-17)19-7-9-22(26)10-8-19/h3-10,13-14,26H,11-12,15-16H2,1-2H3
SMILES Code
OC1=CC=C(C2=CC=C(CN3CC4=C(C=C(OC)C(OC)=C4)CC3)C=C2)C=C1
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
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
Biological target:
MC70 is a potent and non-selective P-glycoprotein (P-gp) inhibitor with an EC50 of 0.69 µM.
In vitro activity:
By contrast, MC70 was found to inhibit cell growth in colon cancer cells without affecting doxorubicin efficacy and in combination with topoisomerase I inhibitors it could be a promising therapeutic approach. What is more, it was also observed that MC70 induced apoptosis, canceled in favor of necrosis when given in combination with high doses of doxorubicin. MC70 inhibited cell migration probably through its interaction with sigma-1 receptor.
Reference: Eur J Pharmacol. 2011 Nov 16;670(1):74-84. https://pubmed.ncbi.nlm.nih.gov/21925160/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
375.47
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 |
Formulation protocol:
1. Fusi F, Durante M, Sticozzi C, Frosini M, Perrone MG, Colabufo NA, Saponara S. Vascular Toxicity Risk Assessment of MC18 and MC70, Novel Potential Diagnostic Tools for In Vivo PET Studies. Basic Clin Pharmacol Toxicol. 2017 May;120(5):434-441. doi: 10.1111/bcpt.12719. Epub 2017 Jan 16. PMID: 27888581.
2. Azzariti A, Quatrale AE, Porcelli L, Colabufo NA, Cantore M, Cassano G, Gasparre G, Iannelli G, Tommasi S, Panaro MA, Paradiso A. MC70 potentiates doxorubicin efficacy in colon and breast cancer in vitro treatment. Eur J Pharmacol. 2011 Nov 16;670(1):74-84. doi: 10.1016/j.ejphar.2011.08.025. Epub 2011 Sep 5. PMID: 21925160.
In vitro protocol:
1. Fusi F, Durante M, Sticozzi C, Frosini M, Perrone MG, Colabufo NA, Saponara S. Vascular Toxicity Risk Assessment of MC18 and MC70, Novel Potential Diagnostic Tools for In Vivo PET Studies. Basic Clin Pharmacol Toxicol. 2017 May;120(5):434-441. doi: 10.1111/bcpt.12719. Epub 2017 Jan 16. PMID: 27888581.
2. Azzariti A, Quatrale AE, Porcelli L, Colabufo NA, Cantore M, Cassano G, Gasparre G, Iannelli G, Tommasi S, Panaro MA, Paradiso A. MC70 potentiates doxorubicin efficacy in colon and breast cancer in vitro treatment. Eur J Pharmacol. 2011 Nov 16;670(1):74-84. doi: 10.1016/j.ejphar.2011.08.025. Epub 2011 Sep 5. PMID: 21925160.
1: Guglielmo S, Lazzarato L, Contino M, Perrone MG, Chegaev K, Carrieri A, Fruttero R, Colabufo NA, Gasco A. SAR Studies on Tetrahydroisoquinoline Derivatives: [4'-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)biphenyl-4-ol] (MC70(1)) Conjugated Through Flexible Alkyl Chains with Furazan Moieties Gives Rise to Potent and Selective Ligands of P-glycoprotein. J Med Chem. 2016 Jun 23. [Epub ahead of print] PubMed PMID: 27336199.
2: Guglielmo S, Contino M, Lazzarato L, Perrone MG, Blangetti M, Fruttero R, Colabufo NA. A Potent and Selective P-gp Modulator for Altering Multidrug Resistance Due to Pump Overexpression. ChemMedChem. 2016 Feb 17;11(4):374-6. doi: 10.1002/cmdc.201500538. Epub 2016 Jan 21. PubMed PMID: 26797828.
3: Capparelli E, Contino M, Perrone MG, Berardi F, Perrone R, Leopoldo M, Colabufo NA. Functionalized Coumarine Fragment to Obtain Fluorescent and Selective P-Glycoprotein Ligands. Arch Pharm (Weinheim). 2016 Mar;349(3):161-7. doi: 10.1002/ardp.201500325. Epub 2016 Jan 11. PubMed PMID: 26750618.
4: Chopra A. O-[(11)C]methyl derivative of 6,7-dimethoxy-2-(4-methoxy-biphenyl-4-yl-methyl)-1,2,3,4-tetrahydro-isoquinoline. 2012 Nov 05 [updated 2013 Jan 31]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK116755/ PubMed PMID: 23390669.
5: Colabufo NA, Contino M, Berardi F, Perrone R, Panaro MA, Cianciulli A, Mitolo V, Azzariti A, Quatrale A, Paradiso A. A new generation of MDR modulating agents with dual activity: P-gp inhibitor and iNOS inducer agents. Toxicol In Vitro. 2011 Feb;25(1):222-30. doi: 10.1016/j.tiv.2010.11.004. Epub 2010 Nov 13. PubMed PMID: 21078380.
6: Colabufo NA, Berardi F, Perrone MG, Cantore M, Contino M, Inglese C, Niso M, Perrone R. Multi-drug-resistance-reverting agents: 2-aryloxazole and 2-arylthiazole derivatives as potent BCRP or MRP1 inhibitors. ChemMedChem. 2009 Feb;4(2):188-95. doi: 10.1002/cmdc.200800329. PubMed PMID: 19140144.
