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MedKoo CAT#: 406602
CAS#: 1472611-44-1 (TFA)
Description: Pyridostatin stabilizes G-quadruplexes (G4s) in cells and elicits a DNA damage response by causing the formation of DNA double strand breaks (DSB). Pyridostatin promotes growth arrest in human cancer cells by inducing replication- and transcription-dependent DNA damage. Pyridostatin targets gene bodies containing clusters of sequences with a propensity for G-quadruplex formation. As a result, pyridostatin modulated the expression of these genes, including the proto-oncogene SRC.
MedKoo Cat#: 406602
Name: Pyridostatin TFA salt
CAS#: 1472611-44-1 (TFA)
Chemical Formula: C37H35F9N8O11
Exact Mass: 596.24957
Molecular Weight: 938.72
Elemental Analysis: C, 47.34; H, 3.76; F, 18.21; N, 11.94; O, 18.75
Related CAS #: 1472611-44-1 (TFA) 1085412-37-8 (free base) 1629261-49-9 (HCl)
Synonym: Pyridostatin; PDS; Pyridostatin TFA salt
IUPAC/Chemical Name: 4-(2-aminoethoxy)-N2,N6-bis(4-(2-aminoethoxy)quinolin-2-yl)pyridine-2,6-dicarboxamide tris(2,2,2-trifluoroacetate)
InChi Key: CYYZQGUDHAKBIQ-UHFFFAOYSA-N
InChi Code: InChI=1S/C31H32N8O5.3C2HF3O2/c32-9-12-42-19-15-24(30(40)38-28-17-26(43-13-10-33)20-5-1-3-7-22(20)36-28)35-25(16-19)31(41)39-29-18-27(44-14-11-34)21-6-2-4-8-23(21)37-29;3*3-2(4,5)1(6)7/h1-8,15-18H,9-14,32-34H2,(H,36,38,40)(H,37,39,41);3*(H,6,7)
SMILES Code: O=C(C1=NC(C(NC2=NC3=CC=CC=C3C(OCCN)=C2)=O)=CC(OCCN)=C1)NC4=NC5=CC=CC=C5C(OCCN)=C4.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F
1: Marchand A, Granzhan A, Iida K, Tsushima Y, Ma Y, Nagasawa K, Teulade-Fichou M, Gabelica V. Ligand-Induced Conformational Changes with Cation Ejection upon Binding to Human Telomeric DNA G-Quadruplexes. J Am Chem Soc. 2015 Jan 6. [Epub ahead of print] PubMed PMID: 25525863.
2: Murat P, Zhong J, Lekieffre L, Cowieson NP, Clancy JL, Preiss T, Balasubramanian S, Khanna R, Tellam J. G-quadruplexes regulate Epstein-Barr virus-encoded nuclear antigen 1 mRNA translation. Nat Chem Biol. 2014 May;10(5):358-64. doi: 10.1038/nchembio.1479. Epub 2014 Mar 16. PubMed PMID: 24633353; PubMed Central PMCID: PMC4188979.
3: Murat P, Gormally MV, Sanders D, Di Antonio M, Balasubramanian S. Light-mediated in cell downregulation of G-quadruplex-containing genes using a photo-caged ligand. Chem Commun (Camb). 2013 Oct 4;49(76):8453-5. doi: 10.1039/c3cc44737e. PubMed PMID: 23949446; PubMed Central PMCID: PMC4155816.
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5: McLuckie KI, Di Antonio M, Zecchini H, Xian J, Caldas C, Krippendorff BF, Tannahill D, Lowe C, Balasubramanian S. G-quadruplex DNA as a molecular target for induced synthetic lethality in cancer cells. J Am Chem Soc. 2013 Jul 3;135(26):9640-3. doi: 10.1021/ja404868t. Epub 2013 Jun 25. PubMed PMID: 23782415; PubMed Central PMCID: PMC3964824.
6: Müller S, Sanders DA, Di Antonio M, Matsis S, Riou JF, Rodriguez R, Balasubramanian S. Pyridostatin analogues promote telomere dysfunction and long-term growth inhibition in human cancer cells. Org Biomol Chem. 2012 Aug 28;10(32):6537-46. doi: 10.1039/c2ob25830g. Epub 2012 Jul 13. PubMed PMID: 22790277; PubMed Central PMCID: PMC3700226.
7: Mergny JL. Alternative DNA structures: G4 DNA in cells: itae missa est? Nat Chem Biol. 2012 Feb 15;8(3):225-6. doi: 10.1038/nchembio.793. PubMed PMID: 22337092.
8: Rodriguez R, Miller KM, Forment JV, Bradshaw CR, Nikan M, Britton S, Oelschlaegel T, Xhemalce B, Balasubramanian S, Jackson SP. Small-molecule-induced DNA damage identifies alternative DNA structures in human genes. Nat Chem Biol. 2012 Feb 5;8(3):301-10. doi: 10.1038/nchembio.780. PubMed PMID: 22306580; PubMed Central PMCID: PMC3433707.
9: Mela I, Kranaster R, Henderson RM, Balasubramanian S, Edwardson JM. Demonstration of ligand decoration, and ligand-induced perturbation, of G-quadruplexes in a plasmid using atomic force microscopy. Biochemistry. 2012 Jan 17;51(2):578-85. doi: 10.1021/bi201600g. Epub 2012 Jan 6. PubMed PMID: 22225525.
10: Koirala D, Dhakal S, Ashbridge B, Sannohe Y, Rodriguez R, Sugiyama H, Balasubramanian S, Mao H. A single-molecule platform for investigation of interactions between G-quadruplexes and small-molecule ligands. Nat Chem. 2011 Aug 28;3(10):782-7. doi: 10.1038/nchem.1126. PubMed PMID: 21941250; PubMed Central PMCID: PMC3277938.
11: McCauley MJ, Williams MC. Single-molecule biophysics: untying a nanoscale knot. Nat Chem. 2011 Sep 23;3(10):754-5. doi: 10.1038/nchem.1159. PubMed PMID: 21941242.
