MedKoo Cat#: 558277 | Name: Vacquinol-1
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Description:

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

Vacquinol-1, also known as NSC 13316, is an activator of MKK4-dependent macropinocytotic cell death in glioblastoma cells. Vacquinol-1 has beneficial effects on a glioblastoma multiforme mouse model by oral administration. In glioblastoma cells, Vacquinol-1 targets macropinocytosis, a cellular process that will not lead to cell death in normal cells.

Chemical Structure

Vacquinol-1
Vacquinol-1
CAS#5428-80-8

Theoretical Analysis

MedKoo Cat#: 558277

Name: Vacquinol-1

CAS#: 5428-80-8

Chemical Formula: C21H21ClN2O

Exact Mass: 352.1342

Molecular Weight: 352.86

Elemental Analysis: C, 71.48; H, 6.00; Cl, 10.05; N, 7.94; O, 4.53

Price and Availability

Size Price Availability Quantity
100mg USD 1,250.00
200mg USD 1,950.00
500mg USD 2,650.00
1g USD 3,250.00
2g USD 4,950.00
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Related CAS #
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Synonym
NSC 13316; NSC-13316; NSC13316; Vacquinol-1
IUPAC/Chemical Name
(2-(4-chlorophenyl)quinolin-4-yl)(piperidin-2-yl)methanol
InChi Key
VKLJPGAHSLIQKH-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H21ClN2O/c22-15-10-8-14(9-11-15)20-13-17(16-5-1-2-6-18(16)24-20)21(25)19-7-3-4-12-23-19/h1-2,5-6,8-11,13,19,21,23,25H,3-4,7,12H2
SMILES Code
ClC1=CC=C(C2=NC(C=CC=C3)=C3C(C(O)C4NCCCC4)=C2)C=C1
Appearance
White to beige 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 352.86 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: Jiang C, Liu R, Wu X. Alcohol dehydrogenase-1B represses the proliferation, invasion and migration of breast cancer cells by inactivating the mitogen- activated protein kinase signalling pathway. J Physiol Pharmacol. 2023 Oct;74(5). doi: 10.26402/jpp.2023.5.10. Epub 2023 Dec 6. PMID: 38085522. 2: Kwak D, Hammarström LGJ, Haraldsson M, Ernfors P. Glioblastoma cytotoxicity conferred through dual disruption of endolysosomal homeostasis by Vacquinol-1. Neurooncol Adv. 2021 Oct 15;3(1):vdab152. doi: 10.1093/noajnl/vdab152. PMID: 34765974; PMCID: PMC8577523. 3: Wu C, Chen W, Ding H, Li D, Wen G, Zhang C, Lu W, Chen M, Yang Y. Salvianolic acid B exerts anti-liver fibrosis effects via inhibition of MAPK-mediated phospho-Smad2/3 at linker regions in vivo and in vitro. Life Sci. 2019 Dec 15;239:116881. doi: 10.1016/j.lfs.2019.116881. Epub 2019 Oct 31. PMID: 31678285. 4: Xie Y, Ding J, Cui X, Wu M, Huang C, Zhang R, Wang J, Li X, Cen S, Zhou J. Screening of kinase inhibitors downregulating PD-L1 expression via on/in cell quantitative immunoblots. Eur J Pharm Sci. 2020 Jan 15;142:105088. doi: 10.1016/j.ejps.2019.105088. Epub 2019 Oct 15. PMID: 31626963. 5: Colin M, Delporte C, Janky R, Lechon AS, Renard G, Van Antwerpen P, Maltese WA, Mathieu V. Dysregulation of Macropinocytosis Processes in Glioblastomas May Be Exploited to Increase Intracellular Anti-Cancer Drug Levels: The Example of Temozolomide. Cancers (Basel). 2019 Mar 22;11(3):411. doi: 10.3390/cancers11030411. PMID: 30909495; PMCID: PMC6468498. 6: Sun SL, Li X, Su N, Chen S, Gao X, Zhang G, Piao H. Vacquinol‑1 induces apoptosis in hepatocellular carcinoma cell. Mol Med Rep. 2018 Jul;18(1):557-563. doi: 10.3892/mmr.2018.8957. Epub 2018 May 3. PMID: 29749500. 7: Ahlstedt J, Förnvik K, Zolfaghari S, Kwak D, Hammarström LGJ, Ernfors P, Salford LG, Redebrandt HN. Evaluating vacquinol-1 in rats carrying glioblastoma models RG2 and NS1. Oncotarget. 2018 Jan 3;9(9):8391-8399. doi: 10.18632/oncotarget.23842. PMID: 29492202; PMCID: PMC5823554. 8: Sander P, Mostafa H, Soboh A, Schneider JM, Pala A, Baron AK, Moepps B, Wirtz CR, Georgieff M, Schneider M. Vacquinol-1 inducible cell death in glioblastoma multiforme is counter regulated by TRPM7 activity induced by exogenous ATP. Oncotarget. 2017 May 23;8(21):35124-35137. doi: 10.18632/oncotarget.16703. PMID: 28410232; PMCID: PMC5471040. 9: Hammarström LG, Harmel RK, Granath M, Ringom R, Gravenfors Y, Färnegårdh K, Svensson PH, Wennman D, Lundin G, Roddis Y, Kitambi SS, Bernlind A, Lehmann F, Ernfors P. The Oncolytic Efficacy and in Vivo Pharmacokinetics of [2-(4-Chlorophenyl)quinolin-4-yl](piperidine-2-yl)methanol (Vacquinol-1) Are Governed by Distinct Stereochemical Features. J Med Chem. 2016 Sep 22;59(18):8577-92. doi: 10.1021/acs.jmedchem.6b01009. Epub 2016 Sep 8. PMID: 27607569. 10: Feng X, Zhu W, Schurig-Briccio LA, Lindert S, Shoen C, Hitchings R, Li J, Wang Y, Baig N, Zhou T, Kim BK, Crick DC, Cynamon M, McCammon JA, Gennis RB, Oldfield E. Antiinfectives targeting enzymes and the proton motive force. Proc Natl Acad Sci U S A. 2015 Dec 22;112(51):E7073-82. doi: 10.1073/pnas.1521988112. Epub 2015 Dec 7. PMID: 26644565; PMCID: PMC4697371. 11: Aki T, Funakoshi T, Uemura K. Regulated necrosis and its implications in toxicology. Toxicology. 2015 Jul 3;333:118-126. doi: 10.1016/j.tox.2015.04.003. Epub 2015 Apr 9. PMID: 25865964. 12: Shi Y, Lim SK, Parada LF. The soft underbelly of tumor cells. Cell Res. 2014 Aug;24(8):910-1. doi: 10.1038/cr.2014.72. Epub 2014 May 30. PMID: 24874955; PMCID: PMC4123293. 13: Gilbertson RJ. Driving glioblastoma to drink. Cell. 2014 Apr 10;157(2):289-290. doi: 10.1016/j.cell.2014.03.034. PMID: 24725398. 14: Kitambi SS, Toledo EM, Usoskin D, Wee S, Harisankar A, Svensson R, Sigmundsson K, Kalderén C, Niklasson M, Kundu S, Aranda S, Westermark B, Uhrbom L, Andäng M, Damberg P, Nelander S, Arenas E, Artursson P, Walfridsson J, Forsberg Nilsson K, Hammarström LGJ, Ernfors P. RETRACTED: Vulnerability of glioblastoma cells to catastrophic vacuolization and death induced by a small molecule. Cell. 2014 Apr 10;157(2):313-328. doi: 10.1016/j.cell.2014.02.021. Epub 2014 Mar 20. Retraction in: Cell. 2017 Jul 13;170(2):407. doi: 10.1016/j.cell.2017.06.044. PMID: 24656405.