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MedKoo Cat#: 525226 | Name: Telomestatin

Description:

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

Telomestatin is a novel inhibitor of the telomerase activity inducing the formation of basket-type G-quadruplex (G4) structures from hybrid-type G-quadruplexes in the telomeric region.

Chemical Structure

Telomestatin
Telomestatin
CAS#265114-54-3

Theoretical Analysis

MedKoo Cat#: 525226

Name: Telomestatin

CAS#: 265114-54-3

Chemical Formula: C26H14N8O7S

Exact Mass: 582.0706

Molecular Weight: 582.51

Elemental Analysis: C, 53.61; H, 2.42; N, 19.24; O, 19.23; S, 5.50

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Telomestatin; (R)-Telomestatin; GM 95; GM-95; GM95; SOT 095; SOT-095; SOT095;
IUPAC/Chemical Name
(1R)-4,8-Dimethyl-3,7,11,15,19,23,27-heptaoxa-31-thia-33,34,35,36,37,38,39,40-octaazanonacyclo[28.2.1.12,5.16,9.110,13.114,17.118,21.122,25.126,29]tetraconta-2(40),4,6(39),8,10(38),12,14 (37),16,18(36),20,22(35),24,26(34),28,30(33)-pentadecaene
InChi Key
YVSQVYZBDXIXCC-INIZCTEOSA-N
InChi Code
InChI=1S/C26H14N8O7S/c1-9-17-24-30-14(6-39-24)21-28-12(4-37-21)19-27-11(3-35-19)20-29-13(5-36-20)22-31-15(7-38-22)26-32-16(8-42-26)23-33-18(10(2)40-23)25(34-17)41-9/h3-7,16H,8H2,1-2H3/t16-/m0/s1
SMILES Code
CC(O1)=C2C3=NC(C4=NC(C5=NC(C6=NC(C7=NC(C8=N[C@@H](CS8)C9=NC(C1=N2)=C(O9)C)=CO7)=CO6)=CO5)=CO4)=CO3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 582.51 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: Abraham Punnoose J, Ma Y, Li Y, Sakuma M, Mandal S, Nagasawa K, Mao H. Adaptive and Specific Recognition of Telomeric G-quadruplexes via Polyvalency Induced Unstacking of Binding Units. J Am Chem Soc. 2017 May 15. doi: 10.1021/jacs.7b00607. [Epub ahead of print] PubMed PMID: 28505453. 2: Maleki P, Ma Y, Iida K, Nagasawa K, Balci H. A single molecule study of a fluorescently labeled telomestatin derivative and G-quadruplex interactions. Nucleic Acids Res. 2017 Jan 9;45(1):288-295. doi: 10.1093/nar/gkw1090. Epub 2016 Nov 29. PubMed PMID: 27899628; PubMed Central PMCID: PMC5224478. 3: Mulholland K, Wu C. Binding of Telomestatin to a Telomeric G-Quadruplex DNA Probed by All-Atom Molecular Dynamics Simulations with Explicit Solvent. J Chem Inf Model. 2016 Oct 24;56(10):2093-2102. Epub 2016 Sep 27. PubMed PMID: 27632666. 4: Safa L, Gueddouda NM, Thiébaut F, Delagoutte E, Petruseva I, Lavrik O, Mendoza O, Bourdoncle A, Alberti P, Riou JF, Saintomé C. 5' to 3' Unfolding Directionality of DNA Secondary Structures by Replication Protein A: G-QUADRUPLEXES AND DUPLEXES. J Biol Chem. 2016 Sep 30;291(40):21246-21256. Epub 2016 Jul 19. PubMed PMID: 27440048; PubMed Central PMCID: PMC5076531. 5: Calvo EP, Wasserman M. G-Quadruplex ligands: Potent inhibitors of telomerase activity and cell proliferation in Plasmodium falciparum. Mol Biochem Parasitol. 2016 May;207(1):33-8. doi: 10.1016/j.molbiopara.2016.05.009. Epub 2016 May 20. PubMed PMID: 27217226. 6: Hasegawa D, Okabe S, Okamoto K, Nakano I, Shin-ya K, Seimiya H. G-quadruplex ligand-induced DNA damage response coupled with telomere dysfunction and replication stress in glioma stem cells. Biochem Biophys Res Commun. 2016 Feb 26;471(1):75-81. doi: 10.1016/j.bbrc.2016.01.176. Epub 2016 Feb 1. PubMed PMID: 26845351; PubMed Central PMCID: PMC5176359. 7: Ghimire C, Park S, Iida K, Yangyuoru P, Otomo H, Yu Z, Nagasawa K, Sugiyama H, Mao H. Direct quantification of loop interaction and π-π stacking for G-quadruplex stability at the submolecular level. J Am Chem Soc. 2014 Nov 5;136(44):15537-44. doi: 10.1021/ja503585h. Epub 2014 Oct 22. PubMed PMID: 25296000. 8: Iida K, Nagasawa K. Macrocyclic polyoxazoles as G-quadruplex ligands. Chem Rec. 2013 Dec;13(6):539-48. doi: 10.1002/tcr.201300015. Epub 2013 Nov 13. Review. PubMed PMID: 24347328. 9: Bharti SK, Sommers JA, George F, Kuper J, Hamon F, Shin-ya K, Teulade-Fichou MP, Kisker C, Brosh RM Jr. Specialization among iron-sulfur cluster helicases to resolve G-quadruplex DNA structures that threaten genomic stability. J Biol Chem. 2013 Sep 27;288(39):28217-29. doi: 10.1074/jbc.M113.496463. Epub 2013 Aug 9. PubMed PMID: 23935105; PubMed Central PMCID: PMC3784731. 10: Chung WJ, Heddi B, Tera M, Iida K, Nagasawa K, Phan AT. Solution structure of an intramolecular (3 + 1) human telomeric G-quadruplex bound to a telomestatin derivative. J Am Chem Soc. 2013 Sep 11;135(36):13495-501. doi: 10.1021/ja405843r. Epub 2013 Aug 27. PubMed PMID: 23909929. 11: Iida K, Majima S, Nakamura T, Seimiya H, Nagasawa K. Evaluation of the interaction between long telomeric DNA and macrocyclic hexaoxazole (6OTD) dimer of a G-quadruplex ligand. Molecules. 2013 Apr 12;18(4):4328-41. doi: 10.3390/molecules18044328. PubMed PMID: 23584054. 12: Watson LA, Solomon LA, Li JR, Jiang Y, Edwards M, Shin-ya K, Beier F, Bérubé NG. Atrx deficiency induces telomere dysfunction, endocrine defects, and reduced life span. J Clin Invest. 2013 May;123(5):2049-63. doi: 10.1172/JCI65634. Epub 2013 Apr 8. PubMed PMID: 23563309; PubMed Central PMCID: PMC3635723. 13: Wu Y, Sommers JA, Loiland JA, Kitao H, Kuper J, Kisker C, Brosh RM Jr. The Q motif of Fanconi anemia group J protein (FANCJ) DNA helicase regulates its dimerization, DNA binding, and DNA repair function. J Biol Chem. 2012 Jun 22;287(26):21699-716. doi: 10.1074/jbc.M112.351338. Epub 2012 May 10. PubMed PMID: 22582397; PubMed Central PMCID: PMC3381133. 14: Alcaro S, Costa G, Distinto S, Moraca F, Ortuso F, Parrotta L, Artese A. The polymorphisms of DNA G-quadruplex investigated by docking experiments with telomestatin enantiomers. Curr Pharm Des. 2012;18(14):1873-9. PubMed PMID: 22376115. 15: Vy Thi Le T, Han S, Chae J, Park HJ. G-quadruplex binding ligands: from naturally occurring to rationally designed molecules. Curr Pharm Des. 2012;18(14):1948-72. Review. PubMed PMID: 22376113. 16: Miyazaki T, Pan Y, Joshi K, Purohit D, Hu B, Demir H, Mazumder S, Okabe S, Yamori T, Viapiano M, Shin-ya K, Seimiya H, Nakano I. Telomestatin impairs glioma stem cell survival and growth through the disruption of telomeric G-quadruplex and inhibition of the proto-oncogene, c-Myb. Clin Cancer Res. 2012 Mar 1;18(5):1268-80. doi: 10.1158/1078-0432.CCR-11-1795. Epub 2012 Jan 9. PubMed PMID: 22230766; PubMed Central PMCID: PMC3896097. 17: 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. 18: Hamon F, Largy E, Guédin-Beaurepaire A, Rouchon-Dagois M, Sidibe A, Monchaud D, Mergny JL, Riou JF, Nguyen CH, Teulade-Fichou MP. An acyclic oligoheteroaryle that discriminates strongly between diverse G-quadruplex topologies. Angew Chem Int Ed Engl. 2011 Sep 5;50(37):8745-9. doi: 10.1002/anie.201103422. Epub 2011 Aug 2. PubMed PMID: 21812083. 19: Amemiya Y, Furunaga Y, Iida K, Tera M, Nagasawa K, Ikebukuro K, Nakamura C. Analysis of the unbinding force between telomestatin derivatives and human telomeric G-quadruplex by atomic force microscopy. Chem Commun (Camb). 2011 Jul 14;47(26):7485-7. doi: 10.1039/c0cc05781a. Epub 2011 May 5. PubMed PMID: 21547284. 20: Aggarwal M, Sommers JA, Shoemaker RH, Brosh RM Jr. Inhibition of helicase activity by a small molecule impairs Werner syndrome helicase (WRN) function in the cellular response to DNA damage or replication stress. Proc Natl Acad Sci U S A. 2011 Jan 25;108(4):1525-30. doi: 10.1073/pnas.1006423108. Epub 2011 Jan 10. PubMed PMID: 21220316; PubMed Central PMCID: PMC3029756.

View History

Temarotene

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