Triciribine
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MedKoo CAT#: 203010

CAS#: 35943-35-2

Description: Triciribine, also known as VQD-002, is a potent AKT inhibitor and a cell-permeable tricyclic nucleoside molecule with potential antineoplastic activity. Triciribine inhibits the phosphorylation, activation, and signalling of Akt-1, -2, and -3, which may result in the inhibition of Akt-expressing tumor cell proliferation. Akts are anti-apoptotic serine/theronine-specific protein kinases that phosphorylate and inactivate components of the apoptotic machinery, including Bcl-xL/Bcl-2-associated death promoter (BAD) and caspase 9.


Chemical Structure

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Triciribine
CAS# 35943-35-2

Theoretical Analysis

MedKoo Cat#: 203010
Name: Triciribine
CAS#: 35943-35-2
Chemical Formula: C13H16N6O4
Exact Mass: 320.1233
Molecular Weight: 320.3
Elemental Analysis: C, 48.75; H, 5.03; N, 26.24; O, 19.98

Price and Availability

Size Price Availability Quantity
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1850.0 2 Weeks
1.0g USD 2850.0 2 Weeks
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Related CAS #: 35943-35-2   61966-08-3  

Synonym: VQD-002; VQD 002; VQD002; NSC-154020; NSC 154020; NSC154020; Triciribine.

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(3-amino-5-methyl-1,4,5,6,8-pentaazaacenaphthylen-1(5H)-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol.

InChi Key: HOGVTUZUJGHKPL-HTVVRFAVSA-N

InChi Code: InChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)/t6-,8-,9-,13-/m1/s1

SMILES Code: O[C@H]1[C@H](N2C=C3C(N)=NN(C)C4=NC=NC2=C34)O[C@H](CO)[C@H]1O

Appearance: Tan 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

Preparing Stock Solutions

The following data is based on the product molecular weight 320.3 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

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1: Sampath D, Malik A, Plunkett W, Nowak B, Williams B, Burton M, Verstovsek S, Faderl S, Garcia-Manero G, List AF, Sebti S, Kantarjian HM, Ravandi F, Lancet JE. Phase I clinical, pharmacokinetic, and pharmacodynamic study of the Akt-inhibitor triciribine phosphate monohydrate in patients with advanced hematologic malignancies. Leuk Res. 2013 Nov;37(11):1461-7. doi: 10.1016/j.leukres.2013.07.034. Epub 2013 Aug 6. PubMed PMID: 23993427.

2: Gloesenkamp CR, Nitzsche B, Ocker M, Di Fazio P, Quint K, Hoffmann B, Scherübl H, Höpfner M. AKT inhibition by triciribine alone or as combination therapy for growth control of gastroenteropancreatic neuroendocrine tumors. Int J Oncol. 2012 Mar;40(3):876-88. doi: 10.3892/ijo.2011.1256. Epub 2011 Nov 7. PubMed PMID: 22075556.

3: Evangelisti C, Ricci F, Tazzari P, Chiarini F, Battistelli M, Falcieri E, Ognibene A, Pagliaro P, Cocco L, McCubrey JA, Martelli AM. Preclinical testing of the Akt inhibitor triciribine in T-cell acute lymphoblastic leukemia. J Cell Physiol. 2011 Mar;226(3):822-31. doi: 10.1002/jcp.22407. PubMed PMID: 20857426.

4: Garrett CR, Coppola D, Wenham RM, Cubitt CL, Neuger AM, Frost TJ, Lush RM, Sullivan DM, Cheng JQ, Sebti SM. Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT. Invest New Drugs. 2011 Dec;29(6):1381-9. doi: 10.1007/s10637-010-9479-2. Epub 2010 Jul 20. PubMed PMID: 20644979.

5: Ptak RG, Gentry BG, Hartman TL, Watson KM, Osterling MC, Buckheit RW Jr, Townsend LB, Drach JC. Inhibition of human immunodeficiency virus type 1 by triciribine involves the accessory protein nef. Antimicrob Agents Chemother. 2010 Apr;54(4):1512-9. doi: 10.1128/AAC.01443-09. Epub 2010 Jan 19. PubMed PMID: 20086149; PubMed Central PMCID: PMC2849366.

6: Dieterle A, Orth R, Daubrawa M, Grotemeier A, Alers S, Ullrich S, Lammers R, Wesselborg S, Stork B. The Akt inhibitor triciribine sensitizes prostate carcinoma cells to TRAIL-induced apoptosis. Int J Cancer. 2009 Aug 15;125(4):932-41. doi: 10.1002/ijc.24374. PubMed PMID: 19422047.

7: Migawa MT, Drach JC, Townsend LB. Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-methyl-1-(beta-D-ribofuranosyl)- and 3-amino-5-methyl-1-(2-deoxy-beta-D-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaaza acenaphthylene as analogues of triciribine. J Med Chem. 2005 Jun 2;48(11):3840-51. PubMed PMID: 15916436.

8: Smith KL, Lai VC, Prigaro BJ, Ding Y, Gunic E, Girardet JL, Zhong W, Hong Z, Lang S, An H. Synthesis of new 2'-beta-C-methyl related triciribine analogues as anti-HCV agents. Bioorg Med Chem Lett. 2004 Jul 5;14(13):3517-20. PubMed PMID: 15177464.

9: Porcari AR, Townsend LB. An improved total synthesis of triciribine: a tricyclic nucleoside with antineoplastic and antiviral properties. Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):31-9. PubMed PMID: 15043134.

10: Porcari AR, Ptak RG, Borysko KZ, Breitenbach JM, Drach JC, Townsend LB. Synthesis and antiviral activity of 2-substituted analogs of triciribine. Nucleosides Nucleotides Nucleic Acids. 2003 Dec;22(12):2171-93. PubMed PMID: 14714765.



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