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Triciribine, 1mg  

Triciribine, 1mg

6-Amino-4-methyl-8-(β-D-ribofuranosyl)4H,8H-pyrrolo[4,3,2-de]pyrimido[4,5-c] pyridazine    

Synonyms: TCN, Tricyclic Nucleoside, NSC-154020, API-2
inhibits Akt/PKB signaling

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PKI-TCN-001

Availability: within 3 days

145,00 €

Background: Triciribine (TCN, Tricyclic Nucleoside, NSC-154020) inhibits Akt (protein kinase B) signaling resulting in apoptosis of human cancer cells. It also inhibits DNA synthesis and as its monophosphate, is active against HIV type 1. It works in vivo as selective Akt activation inhibitor. The compound is phosphorylated to its active metabolite, the mono-phosphate derivative TCN-P, by adenosine kinase and is able to prevent the phosphorylation of Akt1, Akt2 or Akt3. TCN-P binds to the PH domain of Akt and prevents its recruitment to the plasma membrane and subsequent phosphorylation at T308 and S473. In contrast, constitutively active Akt mutants (Akt1-T308D/S473D and myr-Akt), are resistant to TCN-P.

Molecular weight: 320.3 g/mol
Chemical formula: C13H16N6O4
Purity: >97%
Appearance: Orange to dark red solid
Solubility: DMSO to 100 mM
CAS Number: 35943-35-2

Product specific literature references:

Plagemann PG (1976) "Transport, phosphorylation, and toxicity of a tricyclic nucleoside in cultured Novikoff rat hepatoma cells and other cell lines and relase of its monophosphate by the cells" J. Natl. Cancer Inst. 57(6):1283-95

Basseches PJ, Durski A, Powis G (1982) "High-performance liquid chromatographic assay of the antineoplastic agent tricyclic nucleoside 5\'-phosphate and its disposition in rabbit" J. Chromatogr. 233:227-34

Bennett LL Jr, Allan PW, Chang CH (1983) "Phosphorylation of tricyclic nucleoside by adenosine kinases from L1210 cells and HEp-2 cells" Biochem. Pharmacol. 32(17):2601-2

Schilcher RB, Young JD, Baker LH (1985) "Reversed-phase high-performance liquid chromatographic determination of tricyclic nucleoside and tricyclic nucleoside 5\'-phosphate in biological specimens" J. Chromatogr. 337(1):55-62

Behrens BC, Hamilton TC, Louie KG, Grotzinger KR, McKoy WM, Tsuruo T, Young RC, Ozols RF (1986) "Activity of tricyclic nucleoside 5\'-phosphate in model systems of human ovarian cancer" Invest. New Drugs 4(4):295-304. R

Wotring LL, Crabtree GW, Edwards NL, Parks RE Jr, Townsend LB (1986) "Mechanism of activation of triciribine phosphate (TCN-P) as a prodrug form of TCN" Cancer Treat Rep.70(4):491-7

Wotring LL, Townsend LB, Jones LM, Borysko KZ, Gildersleeve DL, Parker WB (1990) "Dual mechanisms of inhibition of DNA synthesis by triciribine" Cancer Res. 50(16):4891-9.

Kucera LS, Iyer NP, Puckett SH, Buckheit RW Jr, Westbrook L, Toyer BR, White EL, Decker JM, Shannon WM, Chen RC (1993) "Activity of triciribine and triciribine-5\'-monophosphate against human immunodeficiency virus types 1 and 2" AIDS Res Hum Retroviruses. 9(4):307-14

Ptak RG, Borysko KZ, Porcari AR, Buthod JL, Holland LE, Shipman C Jr, Townsend LB, Drach JC (1998) "Phosphorylation of triciribine is necessary for activity against HIV type 1." AIDS Res Hum Retroviruses. 14(15):1315-22.

Porcari AR, Ptak RG, Borysko KZ, Breitenbach JM, Vittori S, Wotring LL, Drach JC, Townsend LB (2000) "Deoxy sugar analogues of triciribine: correlation of antiviral and antiproliferative activity with intracellular phosphorylation" J. Med. Chem. 43(12):2438-48

Yang L, Dan HC, Sun M, Liu Q, Sun XM, Feldman RI, Hamilton AD, Polokoff M, Nicosia SV, Herlyn M, Sebti SM, Cheng JQ. (2004) "Akt/protein kinase B signaling inhibitor-2, a selective small molecule inhibitor of Akt signaling with antitumor activity in cancer cells overexpressing Akt" Cancer Res. 64(13):4394-9

Berndt N, Yang H, Trinczek B, Betzi S, Zhang Z, Wu B, Lawrence NJ, Pellecchia M, Schönbrunn E, Cheng JQ, Sebti SM.(2010) “The Akt activation inhibitor TCN-P inhibits Akt phosphorylation by binding to the PH domain of Akt and blocking its recruitment to the plasma membrane.” Cell Death Differ. 17(11):1795-804.

PLEASE NOTE: This product is designed for research purposes and can only be delivered to academic and business customers.