VLX600
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MedKoo CAT#: 408097

CAS#: 1622945-04-3 (free base)

Description: VLX600 is a Iron Chelator that Target Both Proliferating and Quiescent Cancer Cells. VLX600 potentiated the effect of radiation in tumor spheroids in a synergistic manner. VLX600 is a lipophilic cation-based triazinoindolyl-hydrazone compound and mitochondrial oxidative phosphorylation (OxPhos) inhibitor, with potential antineoplastic activity. Upon infusion, in normal cells and proliferating tumor cells where glucose is readily available,


Price and Availability

Size Price Shipping out time Quantity
50mg USD 350 2 Weeks
100mg USD 550 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1850 2 Weeks
1g USD 2950 2 Weeks
2g USD 5250 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-24. Prices are subject to change without notice.

VLX600 is in stock.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 408097
Name: VLX600
CAS#: 1622945-04-3 (free base)
Chemical Formula: C17H17N7
Exact Mass: 319.1545
Molecular Weight: 319.372
Elemental Analysis: C, 63.93; H, 5.37; N, 30.70


Related CAS #: 327031-55-0 (free base)   1622945-04-3 (free base)    

Synonym: VLX600; VLX-600; VLX 600;

IUPAC/Chemical Name: 1-(2-Pyridinyl)ethanone 2-(4a,5-dihydro-6-methyl-2H-1,2,4-triazino[5,6-b]indol-3-yl)hydrazone

InChi Key: GCXMWESEENEVIC-SRZZPIQSSA-N

InChi Code: InChI=1S/C17H17N7/c1-10-6-5-7-12-14(10)19-16-15(12)22-24-17(20-16)23-21-11(2)13-8-3-4-9-18-13/h3-9,16,19H,1-2H3,(H2,20,23,24)/b21-11+

SMILES Code: C/C(C1=NC=CC=C1)=N\NC2=NC3NC4=C(C=CC=C4C)C3=NN2


Technical Data

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:
>3 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


Additional Information

Upon infusion, in normal cells and proliferating tumor cells where glucose is readily available, inhibition of OxPhos by VLX600 induces a hypoxia-inducible factor 1-alpha (HIF-1alpha)-dependent shift to, and an increase in glycolysis. Glycolysis alone does not produce enough energy to support the growth of tumor cells in this environment, and the induction of autophagy occurs. In the metabolically compromised tumor microenvironment, the availability of oxygen and glucose is limited due to poor vascularization and perfusion of tumor micro-areas. Tumor cells growing in this environment are thus unable to compensate for decreased mitochondrial function by increasing glycolysis. This leads to nutrient depletion, decreased energy production, induction of autophagy, tumor cell death and an inhibition of cell proliferation in quiescent tumor cells. Mitochondrial OxPhos, which is hyperactivated in cancer cells, plays a key role in the promotion of cancer cell proliferation.


References

1: Kanakkanthara A, Kurmi K, Ekstrom TL, Hou X, Purfeerst ER, Heinzen EP, Correia C, Huntoon CJ, O'Brien D, Wahner Hendrickson AE, Dowdy SC, Li H, Oberg AL, Hitosugi T, Kaufmann SH, Weroha SJ, Karnitz LM. BRCA1 Deficiency Upregulates NNMT, Which Reprograms Metabolism and Sensitizes Ovarian Cancer Cells to Mitochondrial Metabolic Targeting Agents. Cancer Res. 2019 Dec 1;79(23):5920-5929. doi: 10.1158/0008-5472.CAN-19-1405. Epub 2019 Oct 16. PMID: 31619387; PMCID: PMC6891213.

2: Karlsson H, Senkowski W, Fryknäs M, Mansoori S, Linder S, Gullbo J, Larsson R, Nygren P. A novel tumor spheroid model identifies selective enhancement of radiation by an inhibitor of oxidative phosphorylation. Oncotarget. 2019 Sep 3;10(51):5372-5382. doi: 10.18632/oncotarget.27166. PMID: 31523395; PMCID: PMC6731106.

3: Mody K, Mansfield AS, Vemireddy L, Nygren P, Gulbo J, Borad M. A phase I study of the safety and tolerability of VLX600, an Iron Chelator, in patients with refractory advanced solid tumors. Invest New Drugs. 2019 Aug;37(4):684-692. doi: 10.1007/s10637-018-0703-9. Epub 2018 Nov 21. PMID: 30460505.

4: Vitiello GA, Medina BD, Zeng S, Bowler TG, Zhang JQ, Loo JK, Param NJ, Liu M, Moral AJ, Zhao JN, Rossi F, Antonescu CR, Balachandran VP, Cross JR, DeMatteo RP. Mitochondrial Inhibition Augments the Efficacy of Imatinib by Resetting the Metabolic Phenotype of Gastrointestinal Stromal Tumor. Clin Cancer Res. 2018 Feb 15;24(4):972-984. doi: 10.1158/1078-0432.CCR-17-2697. Epub 2017 Dec 15. PMID: 29246941; PMCID: PMC5815929.

5: Zhang X, Mofers A, Hydbring P, Olofsson MH, Guo J, Linder S, D'Arcy P. MYC is downregulated by a mitochondrial checkpoint mechanism. Oncotarget. 2017 Oct 6;8(52):90225-90237. doi: 10.18632/oncotarget.21653. PMID: 29163823; PMCID: PMC5685744.

6: Martin TD, Cook DR, Choi MY, Li MZ, Haigis KM, Elledge SJ. A Role for Mitochondrial Translation in Promotion of Viability in K-Ras Mutant Cells. Cell Rep. 2017 Jul 11;20(2):427-438. doi: 10.1016/j.celrep.2017.06.061. PMID: 28700943; PMCID: PMC5553568.

7: Fryknäs M, Zhang X, Bremberg U, Senkowski W, Olofsson MH, Brandt P, Persson I, D'Arcy P, Gullbo J, Nygren P, Schughart LK, Linder S, Larsson R. Iron chelators target both proliferating and quiescent cancer cells. Sci Rep. 2016 Dec 7;6:38343. doi: 10.1038/srep38343. PMID: 27924826; PMCID: PMC5141479.

8: Urra FA, Weiss-López B, Araya-Maturana R. Determinants of Anti-Cancer Effect of Mitochondrial Electron Transport Chain Inhibitors: Bioenergetic Profile and Metabolic Flexibility of Cancer Cells. Curr Pharm Des. 2016;22(39):5998-6008. doi: 10.2174/1381612822666160719122626. PMID: 27510477.

9: Wang L, Zhao S, Bao G, Zhang Y, Xi S, Zhou G, Zhai X, Gong P. Design, Synthesis, and Cytotoxicity of Novel 2,4,6-Trisubstituted 1,3,5- triazines Bearing Aryl Hydrazone Moiety as Potent Antitumor Agent. Med Chem. 2016;12(7):621-630. doi: 10.2174/1573406412666160106154551. PMID: 26732116.

10: Zhang X, Fryknäs M, Hernlund E, Fayad W, De Milito A, Olofsson MH, Gogvadze V, Dang L, Påhlman S, Schughart LA, Rickardson L, D'Arcy P, Gullbo J, Nygren P, Larsson R, Linder S. Induction of mitochondrial dysfunction as a strategy for targeting tumour cells in metabolically compromised microenvironments. Nat Commun. 2014;5:3295. doi: 10.1038/ncomms4295. PMID: 24548894; PMCID: PMC3929804.