GLPBio

KIN-59

Catalog No.: GC16460Purity:>98%Synonyms: 5’-O-Tritylinosine
COASDSData Sheet
KIN-59 is a noncompetitive inhibitor against human and bacterial recombinant thymidine phosphorylase (TPase) with IC50 values of 67 and 44µM respectively.

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KIN-59
Cas No.: 4152-77-6
5mgIn Stock
$33.00
1
10mgIn Stock
$53.00
1
25mgIn Stock
$97.00
1
50mgIn Stock
$153.00
1
100mgIn Stock
$243.00
1
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Description

KIN-59 is a noncompetitive inhibitor against human and bacterial recombinant thymidine phosphorylase (TPase) with IC50 values of 67 and 44µM respectively[1]. KIN-59 is a purine riboside derivative that blocks the enzyme non-competitively with thymidine or phosphate, and requires both the intact 5′-O-trityl group and the ribose–hypoxanthine scaffold for activity[2].

In vitro, KIN-59 (0–100µM) incubated muse aortic endothelial cells (MAECs) for 5 days poorly inhibited cell proliferation with an IC50 value of 78 ± 2µM. KIN-59 also dose-dependently slowed endothelial cell migration in a 16-hour wound-healing assay[3]. KIN-59 (250nmol) incubated fertilized chicken eggs with or without 10µl of TPase for 4 days. KIN-59 not only annihilated the TPase-induced angiogenesis but also efficiently inhibited the formation of normal chick chorioallantoic membrane vessels in the absence of exogenously added TPase[4]. KIN-59 (125–250μM) pretreatment on human or wild-type murine platelets for 5min before collagen, ADP, thrombin or collagen related peptide stimulation reversibly and dose-dependently suppressed induced aggregation[5].

In vivo, KIN-59 (15mg/kg) was injected subcutaneously in immunodeficient nude mice twice daily (once daily during the weekend) until day 20. KIN-59 inhibited the binding of fibroblast growth factor 2 (FGF2) to FGF receptor 1, preventing the growth and neovascularization of subcutaneous tumors induced by FGF2-transformed endothelial cells[6].

References:
[1] Liekens S, Balzarini J, Hernández A I, et al. Thymidine phosphorylase is noncompetitively inhibited by 5'-O-trityl-inosine (KIN59) and related compounds. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):975-80.
[2] Casanova E, Hernandez A I, Priego E M, et al. 5'-O-tritylinosine and analogues as allosteric inhibitors of human thymidine phosphorylase. J Med Chem. 2006 Sep 7;49(18):5562-70.
[3] Liekens, S., Bronckaers, A., Hernández, A.I., et al. 5'-O-tritylated nucleoside derivatives: inhibition of thymidine phosphorylase and angiogenesis. Mol. Pharmacol. 70(2), 501-509 (2006).
[4] Liekens, S., Hernández, A.I., Ribatti, D., et al. The nucleoside derivative 5'-O-trityl-inosine (KIN59) suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action. The Journal of Biological Chemisty 279(28), 29598-29605 (2004).
[5] Li W, Gigante A, Perez-Perez M J, et al. Thymidine phosphorylase participates in platelet signaling and promotes thrombosis. Circ Res. 2014 Dec 5;115(12):997-1006.
[6] Liekens, S., Bronckaers, A., Belleri, M., et al. The thymidine phosphorylase inhibitor 5'-O-tritylinosine (KIN-59) is an antiangiogenic multitarget fibroblast growth factor-2 antagonist. Mol. Cancer Ther. 11(4), 817-829 (2012).

Protocol

Kinase experiment [1]:

Preparation Method

500μL reaction solution containing 10mM Tris-HCl pH 7.6, 1mM EDTA, 150mM NaCl, 2mM phosphate and 100μM thymidine with 0.025U enzyme TPase was incubated for 60min at room temperature. The samples taken at 0, 20, 40, 60min, 100μL aliquots were boiled, cooled and analyzed by RP-8 HPLC (267nm) to quantify thymine formation. KIN-59 (1mM, 100μM, 10μM, and 0μM) were added to the reaction mixture to test for TPase inhibition.

Reaction Conditions

0–1000μM; 60min

Applications

KIN-59 inhibited TPase in a reversible, non-competitive manner with Ki value of about 39μM.
Cell experiment [2]:

Cell lines

Fetal bovine aortic endothelial GM7373 cells

Preparation Method

Serum-starved FGFR1-overexpressing GM7373 cells and VEGFR2-overexpressing GM7373 cells were incubated with 60μM KIN-59 or vehicle for 30min, after which 10ng/mL FGF2 or 30ng/mL VEGF was added.

Reaction Conditions

60μM; 30min

Applications

KIN-59 inhibited FGF2- but not VEGF-stimulated endothelial cell growth.
Animal experiment [2]:

Animal models

Female, athymic, nude nu/nu mice

Preparation Method

Eight-week-old female, athymic, nude nu/nu mice, weighing about 25g, were inoculated subcutaneously with 200mL of serum-free DMEM containing 2×106 F2T-luc2.9 cells. KIN-59 treatment was started after 24 hours and continued till the end of the experiment. KIN-59 was administered subcutaneously at 15mg/kg, twice daily (once daily during the weekend) at a site distant from the tumor (inoculation) site.

Dosage form

15mg/kg; s.c; twice daily (once daily during the weekend)

Applications

KIN-59 inhibited the binding of fibroblast growth factor 2 (FGF2) to FGF receptor 1, preventing the growth and neovascularization of subcutaneous tumors induced by FGF2-transformed endothelial cells.

References:
[1] Liekens, S., Hernández, A.I., Ribatti, D., et al. The nucleoside derivative 5'-O-trityl-inosine (KIN59) suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action. The Journal of Biological Chemisty 279(28), 29598-29605 (2004).
[2] Liekens, S., Bronckaers, A., Belleri, M., et al. The thymidine phosphorylase inhibitor 5'-O-tritylinosine (KIN59) is an antiangiogenic multitarget fibroblast growth factor-2 antagonist. Mol. Cancer Ther. 11(4), 817-829 (2012).

Chemical Properties

CAS No.
4152-77-6
Synonyms
5’-O-Tritylinosine
Chemical Name
5'-O-(triphenylmethyl)-inosine
SMILES
O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=CNC3=O)O[C@@H]1COC(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6
Molecular Formula
C29H26N4O5
Molecular Weight
510.5
Solubility
≤0.3mg/ml in ethanol;16mg/ml in DMSO;5mg/ml in dimethyl formamide
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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