Pyridostatin TFA | CAS#1085412-37-8 | 1472611-44-1 | G-quadruplexe stabilizer

MedKoo Cat#: 406602 | Name: Pyridostatin TFA salt

Description:

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

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.

Chemical Structure

Pyridostatin TFA salt

CAS#1472611-44-1 (TFA)

Theoretical Analysis

MedKoo Cat#: 406602

Name: Pyridostatin TFA salt

CAS#: 1472611-44-1 (TFA)

Chemical Formula: C37H35F9N8O11

Exact Mass: 0.0000

Molecular Weight: 938.72

Elemental Analysis: C, 47.34; H, 3.76; F, 18.21; N, 11.94; O, 18.75

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,950.00	Ready to ship

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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

Appearance

White 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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#CRB50921

QC Data

View QC data: current batch, Lot# CRB50921

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Pyridostatin (RR82) TFA is a G-quadruplex DNA stabilizing agent (Kd=490 nM).

In vitro activity:

For cell lines, the drug is cytotoxic, and this study, therefore, hypothesized that pyridostatin may be toxic for primary neurons as well. To test this, primary rat cortical cultures were transfected with the mApple construct (a red fluorescent protein). Pyridostatin or vehicle was added, and the mApple-expressing neurons were tracked for several days with an automated microscope. Loss of the red mApple fluorescence is a sensitive marker of neuronal death. This study found that treatment with pyridostatin substantially increased the risk of neuronal death in a dose-dependent manner (Fig. 1E). Notably, neurons exposed to pyridostatin retracted neurites before death (Fig. 1D), mimicking neuro-degenerative processes commonly observed in neurons that express ɑ-synuclein, mutant LRRK2 or mutant huntingtin. Reference: Aging (Albany NY). 2017 Sep; 9(9): 1957–1970. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5636668/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	21.30

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 938.72 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. Real-Hohn A, Zhu R, Ganjian H, Ibrahim N, Hinterdorfer P, Kowalski H, Blaas D. Catching Common Cold Virus with a Net: Pyridostatin Forms Filaments in Tris Buffer That Trap Viruses-A Novel Antiviral Strategy? Viruses. 2020 Jul 4;12(7):723. doi: 10.3390/v12070723. PMID: 32635420; PMCID: PMC7412420. 2. Moruno-Manchon JF, Koellhoffer EC, Gopakumar J, Hambarde S, Kim N, McCullough LD, Tsvetkov AS. The G-quadruplex DNA stabilizing drug pyridostatin promotes DNA damage and downregulates transcription of Brca1 in neurons. Aging (Albany NY). 2017 Sep 12;9(9):1957-1970. doi: 10.18632/aging.101282. PMID: 28904242; PMCID: PMC5636668.

In vitro protocol:

In vivo protocol:

TBD

1: Karna D, Liang L, Sharma G, Mandal S, Asamitsu S, Kawamoto Y, Hashiya K, Bando T, Sugiyama H, Mao H. Modulation of dynamic DNA G-quadruplex structures in the hTERT promoter region by ligands. Nucleic Acids Res. 2024 Sep 1:gkae754. doi: 10.1093/nar/gkae754. Epub ahead of print. PMID: 39217470. 2: Keahi DL, Sanders MA, Paul MR, Webster ALH, Fang Y, Wiley TF, Shalaby S, Carroll TS, Chandrasekharappa SC, Sandoval-Garcia C, MacMillan ML, Wagner JE, Hatten ME, Smogorzewska A. G-quadruplexes are a source of vulnerability in BRCA2 deficient granule cell progenitors and medulloblastoma. bioRxiv [Preprint]. 2024 Jul 22:2024.07.20.604431. doi: 10.1101/2024.07.20.604431. PMID: 39091814; PMCID: PMC11291086. 3: Qin G, Liu Z, Yang J, Liao X, Zhao C, Ren J, Qu X. Targeting specific DNA G-quadruplexes with CRISPR-guided G-quadruplex-binding proteins and ligands. Nat Cell Biol. 2024 Jul;26(7):1212-1224. doi: 10.1038/s41556-024-01448-1. Epub 2024 Jul 3. PMID: 38961283. 4: Ma TZ, Liu LY, Zeng YL, Ding K, Zhang H, Liu W, Cao Q, Xia W, Xiong X, Wu C, Mao ZW. G-quadruplex-guided cisplatin triggers multiple pathways in targeted chemotherapy and immunotherapy. Chem Sci. 2024 May 15;15(25):9756-9774. doi: 10.1039/d4sc00643g. PMID: 38939132; PMCID: PMC11206235. 5: Johnson K, Seidel JM, Cech TR. Small molecule telomerase inhibitors are also potent inhibitors of telomeric C-strand synthesis. RNA. 2024 Aug 16;30(9):1213-1226. doi: 10.1261/rna.080043.124. PMID: 38918043; PMCID: PMC11331414. 6: Liu W, He X, Zhu Y, Li Y, Wang Z, Li P, Pan J, Wang J, Chu B, Yang G, Zhang M, He Q, Li Y, Li W, Zhang C. Identification of a conserved G-quadruplex within the E165R of African swine fever virus (ASFV) as a potential antiviral target. J Biol Chem. 2024 Jul;300(7):107453. doi: 10.1016/j.jbc.2024.107453. Epub 2024 Jun 7. PMID: 38852886; PMCID: PMC11261444. 7: Neha N, Das P. Exploring G-quadruplex structure in PRCC-TFE3 fusion oncogene: Plausible use as anti cancer therapy for translocation Renal cell carcinoma (tRCC). J Biotechnol. 2024 Jul 10;390:39-49. doi: 10.1016/j.jbiotec.2024.05.004. Epub 2024 May 11. PMID: 38740306. 8: Donato L, Scimone C, Alibrandi S, Mordà D, Anchesi I, Scalinci SZ, Rinaldi C, D'Angelo R, Sidoti A. Investigating G-quadruplex structures in RPGR gene: Implications for understanding X-linked retinal degeneration. Heliyon. 2024 Apr 18;10(8):e29828. doi: 10.1016/j.heliyon.2024.e29828. PMID: 38699732; PMCID: PMC11063440. 9: Chaurembo AI, Xing N, Chanda F, Li Y, Zhang HJ, Fu LD, Huang JY, Xu YJ, Deng WH, Cui HD, Tong XY, Shu C, Lin HB, Lin KX. Mitofilin in cardiovascular diseases: Insights into the pathogenesis and potential pharmacological interventions. Pharmacol Res. 2024 May;203:107164. doi: 10.1016/j.phrs.2024.107164. Epub 2024 Apr 2. PMID: 38569981. 10: Chen Y, Li J, Niu K, Peng Y, Song Q, Feng Q. G-quadruplex is involved in the regulation of BmSGF1 expression in the Silkworm, Bombyx mori. Insect Sci. 2024 Mar 4. doi: 10.1111/1744-7917.13334. Epub ahead of print. PMID: 38439572. 11: Palma E, Içhedef C, Fernandes C, Belchior A, Raposinho P, Gano L, Miranda A, Moreira D, Lourenço P, Cruz C, Pires AS, Botelho MF, Paulo A. Targeting of G-quadruplex DNA with 99mTc(I)/Re(I) Tricarbonyl Complexes Carrying Pyridostatin Derivatives. Chemistry. 2024 Apr 16;30(22):e202400285. doi: 10.1002/chem.202400285. Epub 2024 Mar 8. PMID: 38386665. 12: Boavida A, Napolitano LM, Santos D, Cortone G, Jegadesan NK, Onesti S, Branzei D, Pisani FM. FANCJ DNA helicase is recruited to the replisome by AND-1 to ensure genome stability. EMBO Rep. 2024 Feb;25(2):876-901. doi: 10.1038/s44319-023-00044-y. Epub 2024 Jan 2. PMID: 38177925; PMCID: PMC10897178. 13: D'Anna L, Miclot T, Bignon E, Perricone U, Barone G, Monari A, Terenzi A. Resolving a guanine-quadruplex structure in the SARS-CoV-2 genome through circular dichroism and multiscale molecular modeling. Chem Sci. 2023 Sep 11;14(41):11332-11339. doi: 10.1039/d3sc04004f. PMID: 37886086; PMCID: PMC10599604. 14: Gemmill DL, Nelson CR, Badmalia MD, Pereira HS, Kerr L, Wolfinger MT, Patel TR. The 3' terminal region of Zika virus RNA contains a conserved G-quadruplex and is unfolded by human DDX17. Biochem Cell Biol. 2024 Feb 1;102(1):96-105. doi: 10.1139/bcb-2023-0036. Epub 2023 Sep 29. PMID: 37774422. 15: Fang P, Xie C, Pan T, Cheng T, Chen W, Xia S, Ding T, Fang J, Zhou Y, Fang L, Wei D, Xiao S. Unfolding of an RNA G-quadruplex motif in the negative strand genome of porcine reproductive and respiratory syndrome virus by host and viral helicases to promote viral replication. Nucleic Acids Res. 2023 Oct 27;51(19):10752-10767. doi: 10.1093/nar/gkad759. PMID: 37739415; PMCID: PMC10602871. 16: Escarcega RD, Patil AA, Moruno-Manchon JF, Urayama A, Marrelli SP, Kim N, Monchaud D, McCullough LD, Tsvetkov AS. Pirh2-dependent DNA damage in neurons induced by the G-quadruplex ligand pyridostatin. J Biol Chem. 2023 Oct;299(10):105157. doi: 10.1016/j.jbc.2023.105157. Epub 2023 Aug 12. PMID: 37579947; PMCID: PMC10534229. 17: Wang J, Huang H, Zhao K, Teng Y, Zhao L, Xu Z, Zheng Y, Zhang L, Li C, Duan Y, Liang K, Zhou X, Cheng X, Xia Y. G-quadruplex in hepatitis B virus pregenomic RNA promotes its translation. J Biol Chem. 2023 Sep;299(9):105151. doi: 10.1016/j.jbc.2023.105151. Epub 2023 Aug 9. PMID: 37567479; PMCID: PMC10485161. 18: Razzaq M, Han JH, Ravichandran S, Kim J, Bae JY, Park MS, Kannappan S, Chung WC, Ahn JH, Song MJ, Kim KK. Stabilization of RNA G-quadruplexes in the SARS- CoV-2 genome inhibits viral infection via translational suppression. Arch Pharm Res. 2023 Jul;46(7):598-615. doi: 10.1007/s12272-023-01458-x. Epub 2023 Aug 10. PMID: 37563335. 19: De Piante E, D'Aria F, Napolitano LMR, Amato J, Pirrello S, Onesti S, Giancola C. Exploring the G-quadruplex binding and unwinding activity of the bacterial FeS helicase DinG. Sci Rep. 2023 Aug 3;13(1):12610. doi: 10.1038/s41598-023-39675-5. PMID: 37537265; PMCID: PMC10400533. 20: Wang Y, Li C, Guo K, Hao X, Hou J, Zhang F, Jin R, Kang C, Gao L. Oxidation- responsive G-quadruplex ligand for selective inhibition of the proliferation of tumour cells. Bioorg Chem. 2023 Oct;139:106746. doi: 10.1016/j.bioorg.2023.106746. Epub 2023 Jul 24. PMID: 37506624.