WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584253
CAS#: 351351-75-2
Description: Braco-19 is a G-quadruplex ligand and inhibits tumor growth.
Hodoodo Cat#: H584253
Name: Braco-19
CAS#: 351351-75-2
Chemical Formula: C35H43N7O2
Exact Mass: 593.35
Molecular Weight: 593.776
Elemental Analysis: C, 70.80; H, 7.30; N, 16.51; O, 5.39
This product is not in stock, which may be available by custom synthesis.
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Synonym: Braco-19
IUPAC/Chemical Name: 1-Pyrrolidinepropanamide, N,N'-(9-((4-(dimethylamino)phenyl)amino)-3,6-acridinediyl)bis-
InChi Key: RKPYSYRMIXRZJT-UHFFFAOYSA-N
InChi Code: InChI=1S/C35H43N7O2/c1-40(2)28-11-7-25(8-12-28)38-35-29-13-9-26(36-33(43)15-21-41-17-3-4-18-41)23-31(29)39-32-24-27(10-14-30(32)35)37-34(44)16-22-42-19-5-6-20-42/h7-14,23-24H,3-6,15-22H2,1-2H3,(H,36,43)(H,37,44)(H,38,39)
SMILES Code: CN(C1=CC=C(NC2=C(C=CC(NC(CCN3CCCC3)=O)=C4)C4=NC5=CC(NC(CCN6CCCC6)=O)=CC=C52)C=C1)C
Appearance: 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
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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 593.78 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: | |
| In vitro protocol: | |
| In vivo protocol: |
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2: Artusi S, Nadai M, Perrone R, Biasolo MA, Palù G, Flamand L, Calistri A, Richter SN. The Herpes Simplex Virus-1 genome contains multiple clusters of repeated G-quadruplex: Implications for the antiviral activity of a G-quadruplex ligand. Antiviral Res. 2015 Jun;118:123-31. doi: 10.1016/j.antiviral.2015.03.016. Epub 2015 Apr 3. PubMed PMID: 25843424.
3: Debray J, Zeghida W, Jourdan M, Monchaud D, Dheu-Andries ML, Dumy P, Teulade-Fichou MP, Demeunynck M. Synthesis and evaluation of fused bispyrimidinoacridines as novel pentacyclic analogues of quadruplex-binder BRACO-19. Org Biomol Chem. 2009 Dec 21;7(24):5219-28. doi: 10.1039/b912716j. Epub 2009 Oct 21. PubMed PMID: 20024118.
4: Zhou G, Liu X, Li Y, Xu S, Ma C, Wu X, Cheng Y, Yu Z, Zhao G, Chen Y. Telomere targeting with a novel G-quadruplex-interactive ligand BRACO-19 induces T-loop disassembly and telomerase displacement in human glioblastoma cells. Oncotarget. 2016 Mar 22;7(12):14925-39. doi: 10.18632/oncotarget.7483. PubMed PMID: 26908447; PubMed Central PMCID: PMC4924762.
5: Gunaratnam M, Greciano O, Martins C, Reszka AP, Schultes CM, Morjani H, Riou JF, Neidle S. Mechanism of acridine-based telomerase inhibition and telomere shortening. Biochem Pharmacol. 2007 Sep 1;74(5):679-89. Epub 2007 Jun 16. PubMed PMID: 17631279.
6: Burger AM, Dai F, Schultes CM, Reszka AP, Moore MJ, Double JA, Neidle S. The G-quadruplex-interactive molecule BRACO-19 inhibits tumor growth, consistent with telomere targeting and interference with telomerase function. Cancer Res. 2005 Feb 15;65(4):1489-96. PubMed PMID: 15735037.
7: Ungvarsky J, Plsikova J, Janovec L, Koval J, Mikes J, Mikesová L, Harvanova D, Fedorocko P, Kristian P, Kasparkova J, Brabec V, Vojtickova M, Sabolova D, Stramova Z, Rosocha J, Imrich J, Kozurkova M. Novel trisubstituted acridines as human telomeric quadruplex binding ligands. Bioorg Chem. 2014 Dec;57:13-29. doi: 10.1016/j.bioorg.2014.07.010. Epub 2014 Aug 10. PubMed PMID: 25171773.
8: Bertrand H, Granzhan A, Monchaud D, Saettel N, Guillot R, Clifford S, Guédin A, Mergny JL, Teulade-Fichou MP. Recognition of G-quadruplex DNA by triangular star-shaped compounds: with or without side chains? Chemistry. 2011 Apr 11;17(16):4529-39. doi: 10.1002/chem.201002810. Epub 2011 Mar 17. PubMed PMID: 21416510.
9: Roe S, Gunaratnam M, Spiteri C, Sharma P, Alharthy RD, Neidle S, Moses JE. Synthesis and biological evaluation of hybrid acridine-HSP90 ligand conjugates as telomerase inhibitors. Org Biomol Chem. 2015 Aug 21;13(31):8500-4. doi: 10.1039/c5ob01177a. PubMed PMID: 26156660.
10: Murphy CT, Gupta A, Armitage BA, Opresko PL. Hybridization of G-quadruplex-forming peptide nucleic acids to guanine-rich DNA templates inhibits DNA polymerase η extension. Biochemistry. 2014 Aug 19;53(32):5315-22. doi: 10.1021/bi5006859. Epub 2014 Aug 5. PubMed PMID: 25068499.
11: Incles CM, Schultes CM, Kempski H, Koehler H, Kelland LR, Neidle S. A G-quadruplex telomere targeting agent produces p16-associated senescence and chromosomal fusions in human prostate cancer cells. Mol Cancer Ther. 2004 Oct;3(10):1201-6. PubMed PMID: 15486186.
12: Gilbert-Girard S, Gravel A, Artusi S, Richter SN, Wallaschek N, Kaufer BB, Flamand L. Stabilization of Telomere G-Quadruplexes Interferes with Human Herpesvirus 6A Chromosomal Integration. J Virol. 2017 Jun 26;91(14). pii: e00402-17. doi: 10.1128/JVI.00402-17. Print 2017 Jul 15. PubMed PMID: 28468887; PubMed Central PMCID: PMC5487558.
13: Tippana R, Hwang H, Opresko PL, Bohr VA, Myong S. Single-molecule imaging reveals a common mechanism shared by G-quadruplex-resolving helicases. Proc Natl Acad Sci U S A. 2016 Jul 26;113(30):8448-53. doi: 10.1073/pnas.1603724113. Epub 2016 Jul 12. PubMed PMID: 27407146; PubMed Central PMCID: PMC4968719.
14: Incles CM, Schultes CM, Kelland LR, Neidle S. Acquired cellular resistance to flavopiridol in a human colon carcinoma cell line involves up-regulation of the telomerase catalytic subunit and telomere elongation. Sensitivity of resistant cells to combination treatment with a telomerase inhibitor. Mol Pharmacol. 2003 Nov;64(5):1101-8. PubMed PMID: 14573759.
15: Norseen J, Johnson FB, Lieberman PM. Role for G-quadruplex RNA binding by Epstein-Barr virus nuclear antigen 1 in DNA replication and metaphase chromosome attachment. J Virol. 2009 Oct;83(20):10336-46. doi: 10.1128/JVI.00747-09. Epub 2009 Aug 5. PubMed PMID: 19656898; PubMed Central PMCID: PMC2753104.
16: Lormand JD, Buncher N, Murphy CT, Kaur P, Lee MY, Burgers P, Wang H, Kunkel TA, Opresko PL. DNA polymerase δ stalls on telomeric lagging strand templates independently from G-quadruplex formation. Nucleic Acids Res. 2013 Dec;41(22):10323-33. doi: 10.1093/nar/gkt813. Epub 2013 Sep 13. PubMed PMID: 24038470; PubMed Central PMCID: PMC3905856.
17: Castillo-González D, Mergny JL, De Rache A, Pérez-Machado G, Cabrera-Pérez MA, Nicolotti O, Introcaso A, Mangiatordi GF, Guédin A, Bourdoncle A, Garrigues T, Pallardó F, Cordeiro MN, Paz-Y-Miño C, Tejera E, Borges F, Cruz-Monteagudo M. Harmonization of QSAR Best Practices and Molecular Docking Provides an Efficient Virtual Screening Tool for Discovering New G-Quadruplex Ligands. J Chem Inf Model. 2015 Oct 26;55(10):2094-110. doi: 10.1021/acs.jcim.5b00415. Epub 2015 Sep 18. PubMed PMID: 26355653.
18: Artese A, Costa G, Ortuso F, Parrotta L, Alcaro S. Identification of new natural DNA G-quadruplex binders selected by a structure-based virtual screening approach. Molecules. 2013 Sep 30;18(10):12051-70. doi: 10.3390/molecules181012051. PubMed PMID: 24084014.
19: Amrane S, Kerkour A, Bedrat A, Vialet B, Andreola ML, Mergny JL. Topology of a DNA G-quadruplex structure formed in the HIV-1 promoter: a potential target for anti-HIV drug development. J Am Chem Soc. 2014 Apr 9;136(14):5249-52. doi: 10.1021/ja501500c. Epub 2014 Mar 27. PubMed PMID: 24649937.
20: Campbell NH, Parkinson GN, Reszka AP, Neidle S. Structural basis of DNA quadruplex recognition by an acridine drug. J Am Chem Soc. 2008 May 28;130(21):6722-4. doi: 10.1021/ja8016973. Epub 2008 May 6. PubMed PMID: 18457389.
