Vacuolin-1
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MedKoo CAT#: 562795

CAS#: 351986-85-1

Description: Vacuolin-1 is a cell-permeable inhibitor of Ca2+ dependent fusion of lysosomes to the cell membrane. It acts by inhibiting release of lysosomal content.


Price and Availability

Size Price Shipping out time Quantity
5mg USD 260 2 Weeks
10mg USD 420 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-06-06. Prices are subject to change without notice.

Vacuolin-1, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 562795
Name: Vacuolin-1
CAS#: 351986-85-1
Chemical Formula: C26H24IN7O
Exact Mass: 577.1087
Molecular Weight: 577.43
Elemental Analysis: C, 54.08; H, 4.19; I, 21.98; N, 16.98; O, 2.77


Synonym: Vacuolin-1; Vacuolin 1; Vacuolin1;

IUPAC/Chemical Name: 3-Iodobenzaldehyde [4-(diphenylamino)-6-(4-morpholinyl)-1,3,5-triazin-2-yl]hydrazone

InChi Key: JMEJTSRAQUFNOP-TURZUDJPSA-N

InChi Code: InChI=1S/C26H24IN7O/c27-21-9-7-8-20(18-21)19-28-32-24-29-25(33-14-16-35-17-15-33)31-26(30-24)34(22-10-3-1-4-11-22)23-12-5-2-6-13-23/h1-13,18-19H,14-17H2,(H,29,30,31,32)/b28-19+

SMILES Code: IC1=CC(/C=N/NC2=NC(N(C3=CC=CC=C3)C4=CC=CC=C4)=NC(N5CCOCC5)=N2)=CC=C1


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:
>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


References

1: Vacuolin-1 potently and reversibly inhibits autophagy by activating Rab5. Autophagy. 2018;14(1):176-177. doi: 10.1080/15548627.2017.1367474. Epub 2018 Feb 1. PubMed PMID: 29388871; PubMed Central PMCID: PMC5846563.

2: Layhadi JA, Fountain SJ. P2X4 Receptor-Dependent Ca(2+) Influx in Model Human Monocytes and Macrophages. Int J Mol Sci. 2017 Oct 27;18(11). pii: E2261. doi: 10.3390/ijms18112261. PubMed PMID: 29077063; PubMed Central PMCID: PMC5713231.

3: Jiang LQ, Wang TY, Webster TJ, Duan HJ, Qiu JY, Zhao ZM, Yin XX, Zheng CL. Intracellular disposition of chitosan nanoparticles in macrophages: intracellular uptake, exocytosis, and intercellular transport. Int J Nanomedicine. 2017 Aug 31;12:6383-6398. doi: 10.2147/IJN.S142060. eCollection 2017. PubMed PMID: 28919742; PubMed Central PMCID: PMC5587219.

4: Li Z, Mbah NE, Maltese WA. Vacuole-inducing compounds that disrupt endolysosomal trafficking stimulate production of exosomes by glioblastoma cells. Mol Cell Biochem. 2018 Feb;439(1-2):1-9. doi: 10.1007/s11010-017-3130-x. Epub 2017 Aug 2. PubMed PMID: 28770472; PubMed Central PMCID: PMC5796851.

5: Chen C, Lu Y, Siu HM, Guan J, Zhu L, Zhang S, Yue J, Zhang L. Identification of Novel Vacuolin-1 Analogues as Autophagy Inhibitors by Virtual Drug Screening and Chemical Synthesis. Molecules. 2017 May 27;22(6). pii: E891. doi: 10.3390/molecules22060891. PubMed PMID: 28555021.

6: Cao Q, Yang Y, Zhong XZ, Dong XP. The lysosomal Ca(2+) release channel TRPML1 regulates lysosome size by activating calmodulin. J Biol Chem. 2017 May 19;292(20):8424-8435. doi: 10.1074/jbc.M116.772160. Epub 2017 Mar 30. PubMed PMID: 28360104; PubMed Central PMCID: PMC5437247.

7: Fekri F, Delos Santos RC, Karshafian R, Antonescu CN. Ultrasound Microbubble Treatment Enhances Clathrin-Mediated Endocytosis and Fluid-Phase Uptake through Distinct Mechanisms. PLoS One. 2016 Jun 8;11(6):e0156754. doi: 10.1371/journal.pone.0156754. eCollection 2016. PubMed PMID: 27275866; PubMed Central PMCID: PMC4898768.

8: Sano O, Kazetani K, Funata M, Fukuda Y, Matsui J, Iwata H. Vacuolin-1 inhibits autophagy by impairing lysosomal maturation via PIKfyve inhibition. FEBS Lett. 2016 Jun;590(11):1576-85. doi: 10.1002/1873-3468.12195. Epub 2016 May 13. PubMed PMID: 27135648.

9: Zou J, Hu B, Arpag S, Yan Q, Hamilton A, Zeng YS, Vanoye CG, Li J. Reactivation of Lysosomal Ca2+ Efflux Rescues Abnormal Lysosomal Storage in FIG4-Deficient Cells. J Neurosci. 2015 Apr 29;35(17):6801-12. doi: 10.1523/JNEUROSCI.4442-14.2015. PubMed PMID: 25926456; PubMed Central PMCID: PMC4412898.

10: Lu Y, Dong S, Hao B, Li C, Zhu K, Guo W, Wang Q, Cheung KH, Wong CW, Wu WT, Markus H, Yue J. Vacuolin-1 potently and reversibly inhibits autophagosome-lysosome fusion by activating RAB5A. Autophagy. 2014;10(11):1895-905. doi: 10.4161/auto.32200. Epub 2014 Oct 30. Erratum in: Autophagy. 2018;14 (1):176-177. PubMed PMID: 25483964; PubMed Central PMCID: PMC4502727.

11: Kypri E, Falkenstein K, De Lozanne A. Antagonistic control of lysosomal fusion by Rab14 and the Lyst-related protein LvsB. Traffic. 2013 May;14(5):599-609. doi: 10.1111/tra.12058. Epub 2013 Mar 12. PubMed PMID: 23387437; PubMed Central PMCID: PMC3622840.

12: Jung J, Shin YH, Konishi H, Lee SJ, Kiyama H. Possible ATP release through lysosomal exocytosis from primary sensory neurons. Biochem Biophys Res Commun. 2013 Jan 11;430(2):488-93. doi: 10.1016/j.bbrc.2012.12.009. Epub 2012 Dec 10. PubMed PMID: 23237805.

13: Shin YH, Lee SJ, Jung J. Secretion of ATP from Schwann cells through lysosomal exocytosis during Wallerian degeneration. Biochem Biophys Res Commun. 2012 Dec 14;429(3-4):163-7. doi: 10.1016/j.bbrc.2012.10.121. Epub 2012 Nov 7. PubMed PMID: 23142593.

14: Liu Y, Zhou Y, Zhu K. Inhibition of glioma cell lysosome exocytosis inhibits glioma invasion. PLoS One. 2012;7(9):e45910. doi: 10.1371/journal.pone.0045910. Epub 2012 Sep 28. PubMed PMID: 23029308; PubMed Central PMCID: PMC3461042.

15: Miller ME, Adhikary S, Kolokoltsov AA, Davey RA. Ebolavirus requires acid sphingomyelinase activity and plasma membrane sphingomyelin for infection. J Virol. 2012 Jul;86(14):7473-83. doi: 10.1128/JVI.00136-12. Epub 2012 May 9. PubMed PMID: 22573858; PubMed Central PMCID: PMC3416309.

16: Keerthivasan G, Liu H, Gump JM, Dowdy SF, Wickrema A, Crispino JD. A novel role for survivin in erythroblast enucleation. Haematologica. 2012 Oct;97(10):1471-9. doi: 10.3324/haematol.2011.061093. Epub 2012 Apr 4. PubMed PMID: 22491741; PubMed Central PMCID: PMC3487547.

17: Durchfort N, Verhoef S, Vaughn MB, Shrestha R, Adam D, Kaplan J, Ward DM. The enlarged lysosomes in beige j cells result from decreased lysosome fission and not increased lysosome fusion. Traffic. 2012 Jan;13(1):108-19. doi: 10.1111/j.1600-0854.2011.01300.x. Epub 2011 Nov 9. PubMed PMID: 21985295; PubMed Central PMCID: PMC3237799.

18: Keerthivasan G, Small S, Liu H, Wickrema A, Crispino JD. Vesicle trafficking plays a novel role in erythroblast enucleation. Blood. 2010 Oct 28;116(17):3331-40. doi: 10.1182/blood-2010-03-277426. Epub 2010 Jul 19. PubMed PMID: 20644112; PubMed Central PMCID: PMC2995360.

19: Bao JX, Xia M, Poklis JL, Han WQ, Brimson C, Li PL. Triggering role of acid sphingomyelinase in endothelial lysosome-membrane fusion and dysfunction in coronary arteries. Am J Physiol Heart Circ Physiol. 2010 Mar;298(3):H992-H1002. doi: 10.1152/ajpheart.00958.2009. Epub 2010 Jan 8. PubMed PMID: 20061541; PubMed Central PMCID: PMC2838547.

20: Shaik GM, Dráberová L, Heneberg P, Dráber P. Vacuolin-1-modulated exocytosis and cell resealing in mast cells. Cell Signal. 2009 Aug;21(8):1337-45. doi: 10.1016/j.cellsig.2009.04.001. Epub 2009 Apr 17. PubMed PMID: 19376224.