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.


Chemical Structure

img
Bafilomycin A1
CAS# 88899-55-2

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

Price and Availability

Size Price Availability Quantity
1.0mg USD 345.0 2 Weeks
5.0mg USD 1250.0 2 Weeks
Bulk inquiry

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

Appearance: Solid powder

Purity: >95% (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

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Bafilomycin A1 is a vacuolar H+-ATPase inhibitor with an IC50 of 0.44 nM.
In vitro activity: 697, Nalm-6, RS4;11, NB4, HL-60, K562 and BV173 representing B-ALL (697, Nalm-6, RS4;11), acute myeloid leukemia (NB4, HL-60), and chronic myeloid leukemia (K562, BV173) cells were cultured in the presence of increasing concentrations of bafilomycin A1 (0 nM, 0.5 nM, 1 nM). Cell proliferation was measured using an MTT assay. The results showed that various concentrations of bafilomycin A1 profoundly inhibited the growth of three pediatric B-ALL cell types in culture (Figure 1A). A flow cytometric assay also revealed that bafilomycin A1 effectively inhibited cell division of the three pediatric B-ALL cell lines (Figure 1B). Reference: Haematologica. 2015 Mar;100(3):345-56. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4349273/
In vivo activity: To study the effect of bafilomycin A1 in vivo, the ability of the compound to suppress and kill B-ALL cells was examined in the mouse model of pediatric B-ALL. Bafilomycin A1 extended survival in the bafilomycin A1-treated B-ALL mice with advanced disease compared with control mice, as shown by a Kaplan-Meier curve (Figure 4A). The average time from diagnosis to death was 30.9 days for the vehicle-treated disease control mice (range 20–39 days; n=20) versus 37.2 days for the mice treated with 0.1 mg/kg bafilomycin (range 30–46 days; n=15; P<0.001). More significantly, 1 mg/kg bafilomycin A1 increased survival with a median survival of 42.5 days (range 30–48 days; n=15; P<0.001). (Figure 4A). Reference: Haematologica. 2015 Mar;100(3):345-56. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4349273/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 29.0 46.56
Methanol 5.0 8.03

Preparing Stock Solutions

The following data is based on the product molecular weight 622.84 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
Formulation protocol: 1. 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. PMID: 25512644; PMCID: PMC4349273.
In vitro protocol: 1. 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. PMID: 25512644; PMCID: PMC4349273.
In vivo protocol: 1. 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. PMID: 25512644; PMCID: PMC4349273.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.