Bafilomycin A1
featured

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

MedKoo CAT#: 329893

CAS#: 88899-55-2

Description: Bafilomycin A1, also known as NSC 381866, is a selective, reversible inhibitor of vacuolar H+-ATPases (V-ATPases), blocking these proton pumps in mammalian, plant, or fungal cells with an IC50 value in the 4-400 nM range. Bafilomycin A1 triggers proliferative potential of senescent cancer cells in vitro and in NOD/SCID mice. Bafilomycin A1 induces caspase-independent cell death in hepatocellular carcinoma cells via targeting of autophagy and MAPK pathways.


Price and Availability

Size
Price

1mg
USD 345
Size
Price

5mg
USD 1250
Size
Price

Bafilomycin A1, purity > 95%, 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

img

Theoretical Analysis

MedKoo Cat#: 329893
Name: Bafilomycin A1
CAS#: 88899-55-2
Chemical Formula: C35H58O9
Exact Mass: 622.4081
Molecular Weight: 622.84
Elemental Analysis: C, 67.49; H, 9.39; O, 23.12


Synonym: Bafilomycin A1; NSC 381866; NSC-381866; NSC381866.

IUPAC/Chemical Name: (3E,5E,7R,8S,9S,11E,13Z,15S)-16-((2S,3R,4S)-4-((2R,4R,5S,6R)-2,4-dihydroxy-6-isopropyl-5-methyltetrahydro-2H-pyran-2-yl)-3-hydroxypentan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

InChi Key: XDHNQDDQEHDUTM-XDMBMMISSA-N

InChi Code: InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12-,20-13+,21-16+,29-17+/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33?,35+/m0/s1

SMILES Code: O[C@H]([C@H](C)/C=C(C)/C=C1OC)[C@@H](C)C/C(C)=C/C=C\[C@H](OC)C([C@@H](C)[C@H]([C@@H]([C@@]2(O)C[C@@H](O)[C@H](C)[C@@H]([C@H](C)C)O2)C)O)OC/1=O


Technical Data

Appearance:
Solid powder

Purity:
>95% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
2934990300


References

1: Huenchuguala S, Muñoz P, Segura-Aguilar J. The Importance of Mitophagy in Maintaining Mitochondrial Function in U373MG Cells. Bafilomycin A1 Restores Aminochrome-Induced Mitochondrial Damage. ACS Chem Neurosci. 2017 Oct 18;8(10):2247-2253. doi: 10.1021/acschemneuro.7b00152. Epub 2017 Aug 15. PubMed PMID: 28763613.

2: Yu M, Xu X, Jiang N, Wei W, Li F, He L, Luo X. Dehydropachymic acid decreases bafilomycin A1 induced β-Amyloid accumulation in PC12 cells. J Ethnopharmacol. 2017 Feb 23;198:167-173. doi: 10.1016/j.jep.2017.01.007. Epub 2017 Jan 7. PubMed PMID: 28077330.

3: Was H, Barszcz K, Czarnecka J, Kowalczyk A, Bernas T, Uzarowska E, Koza P, Klejman A, Piwocka K, Kaminska B, Sikora E. Bafilomycin A1 triggers proliferative potential of senescent cancer cells in vitro and in NOD/SCID mice. Oncotarget. 2017 Feb 7;8(6):9303-9322. doi: 10.18632/oncotarget.14066. PubMed PMID: 28030837; PubMed Central PMCID: PMC5354733.

4: Yan Y, Jiang K, Liu P, Zhang X, Dong X, Gao J, Liu Q, Barr MP, Zhang Q, Hou X, Meng S, Gong P. Bafilomycin A1 induces caspase-independent cell death in hepatocellular carcinoma cells via targeting of autophagy and MAPK pathways. Sci Rep. 2016 Nov 15;6:37052. doi: 10.1038/srep37052. PubMed PMID: 27845389; PubMed Central PMCID: PMC5109251.

5: Wang Q, You T, Fan H, Wang Y, Chu T, Poncz M, Zhu L. Rapamycin and bafilomycin A1 alter autophagy and megakaryopoiesis. Platelets. 2017 Jan;28(1):82-89. doi: 10.1080/09537104.2016.1204436. Epub 2016 Aug 18. PubMed PMID: 27534900.

6: Zhu S, Rea SL, Cheng T, Feng HT, Walsh JP, Ratajczak T, Tickner J, Pavlos N, Xu HZ, Xu J. Bafilomycin A1 Attenuates Osteoclast Acidification and Formation, Accompanied by Increased Levels of SQSTM1/p62 Protein. J Cell Biochem. 2016 Jun;117(6):1464-70. doi: 10.1002/jcb.25442. Epub 2015 Nov 26. PubMed PMID: 27043248.

7: Lu X, Chen L, Chen Y, Shao Q, Qin W. Bafilomycin A1 inhibits the growth and metastatic potential of the BEL-7402 liver cancer and HO-8910 ovarian cancer cell lines and induces alterations in their microRNA expression. Exp Ther Med. 2015 Nov;10(5):1829-1834. Epub 2015 Sep 22. PubMed PMID: 26640557; PubMed Central PMCID: PMC4665926.

8: Li LQ, Xie WJ, Pan D. [Effect of bafilomycin A1 on proliferation and oxaliplatin sensitivity in gastric cancer MGC-803 cells]. Nan Fang Yi Ke Da Xue Xue Bao. 2015 Oct;35(10):1400-5. Chinese. PubMed PMID: 26547331.

9: Alesutan I, Musculus K, Castor T, Alzoubi K, Voelkl J, Lang F. Inhibition of Phosphate-Induced Vascular Smooth Muscle Cell Osteo-/Chondrogenic Signaling and Calcification by Bafilomycin A1 and Methylamine. Kidney Blood Press Res. 2015;40(5):490-9. doi: 10.1159/000368524. Epub 2015 Sep 30. PubMed PMID: 26418500.

10: Li LQ, Xie WJ, Pan D, Chen H, Zhang L. Inhibition of autophagy by bafilomycin A1 promotes chemosensitivity of gastric cancer cells. Tumour Biol. 2016 Jan;37(1):653-9. doi: 10.1007/s13277-015-3842-z. Epub 2015 Aug 5. PubMed PMID: 26242265.

11: Mauvezin C, Neufeld TP. Bafilomycin A1 disrupts autophagic flux by inhibiting both V-ATPase-dependent acidification and Ca-P60A/SERCA-dependent autophagosome-lysosome fusion. Autophagy. 2015;11(8):1437-8. doi: 10.1080/15548627.2015.1066957. PubMed PMID: 26156798; PubMed Central PMCID: PMC4590655.

12: Wang S, Liu F, Zeng Z, Yang H, Jiang H. The Protective Effect of Bafilomycin A1 Against Cobalt Nanoparticle-Induced Cytotoxicity and Aseptic Inflammation in Macrophages In Vitro. Biol Trace Elem Res. 2016 Jan;169(1):94-105. doi: 10.1007/s12011-015-0381-9. Epub 2015 Jun 9. PubMed PMID: 26054709.

13: Yuan N, Song L, Zhang S, Lin W, Cao Y, Xu F, Fang Y, Wang Z, Zhang H, Li X, Wang Z, Cai J, Wang J, Zhang Y, Mao X, Zhao W, Hu S, Chen S, Wang J. Bafilomycin A1 targets both autophagy and apoptosis pathways in pediatric B-cell acute lymphoblastic leukemia. Haematologica. 2015 Mar;100(3):345-56. doi: 10.3324/haematol.2014.113324. Epub 2014 Dec 15. PubMed PMID: 25512644; PubMed Central PMCID: PMC4349273.

14: Yeganeh B, Ghavami S, Kroeker AL, Mahood TH, Stelmack GL, Klonisch T, Coombs KM, Halayko AJ. Suppression of influenza A virus replication in human lung epithelial cells by noncytotoxic concentrations bafilomycin A1. Am J Physiol Lung Cell Mol Physiol. 2015 Feb 1;308(3):L270-86. doi: 10.1152/ajplung.00011.2014. Epub 2014 Oct 31. PubMed PMID: 25361566; PubMed Central PMCID: PMC4338931.

15: Inoue S, Setoyama Y, Odaka A. Phagocytosis of bafilomycin A1-treated apoptotic neuroblastoma cells by bone marrow-derived dendritic cells initiates a CD8α+ lymphocyte response to neuroblastoma. J Pediatr Hematol Oncol. 2014 Jul;36(5):e290-5. doi: 10.1097/MPH.0000000000000060. PubMed PMID: 24977403.

16: Inoue S, Setoyama Y, Odaka A. [Comparison of the chemoimmunotherapeutic effect of doxorubicin and bafilomycin-A1 in mouse neuroblastoma cells]. Gan To Kagaku Ryoho. 2014 May;41(5):617-21. Japanese. PubMed PMID: 24917008.

17: Xie Z, Xie Y, Xu Y, Zhou H, Xu W, Dong Q. Bafilomycin A1 inhibits autophagy and induces apoptosis in MG63 osteosarcoma cells. Mol Med Rep. 2014 Aug;10(2):1103-7. doi: 10.3892/mmr.2014.2281. Epub 2014 May 29. PubMed PMID: 24890793.

18: Sun MY, Devaraju P, Xie AX, Holman I, Samones E, Murphy TR, Fiacco TA. Astrocyte calcium microdomains are inhibited by bafilomycin A1 and cannot be replicated by low-level Schaffer collateral stimulation in situ. Cell Calcium. 2014 Jan;55(1):1-16. doi: 10.1016/j.ceca.2013.10.004. Epub 2013 Oct 30. PubMed PMID: 24262208.

19: Hernández-Breijo B, Monserrat J, Román ID, González-Rodríguez Á, Fernández-Moreno MD, Lobo MV, Valverde ÁM, Gisbert JP, Guijarro LG. Azathioprine desensitizes liver cancer cells to insulin-like growth factor 1 and causes apoptosis when it is combined with bafilomycin A1. Toxicol Appl Pharmacol. 2013 Nov 1;272(3):568-78. doi: 10.1016/j.taap.2013.07.024. Epub 2013 Aug 16. PubMed PMID: 23958494.

20: Kapoor S. Bafilomycin A1 and its attenuating effect on tumour growth in systemic malignancies, especially gastrointestinal malignancies. Clin Sci (Lond). 2013 Aug;125(4):219. doi: 10.1042/CS20130057. PubMed PMID: 23480984.