EMAIL THIS PAGE TO A FRIEND

B7651 Sigma

Brefeldin A

from Penicillium brefeldianum, ≥99% (HPLC and TLC)

Synonym: γ,4-Dihydroxy-2-(6-hydroxy-1-heptenyl)-4-cyclopentanecrotonic acid λ-lactone, Ascotoxin, BFA, Cyanein, Decumbin

Purchase

Description

Biochem/physiol Actions

Brefeldin A (BFA) is a fungal metabolite which disrupts the structure and function of the Golgi apparatus. BFA is an activator of the sphingomyelin cycle. Brefeldin A-mediated apoptosis has been observed in human tumor cells.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability


Duolink Webinar

Additional Products to Explore

Ionomycin calcium salt

Ready Made Solution, from Streptomyces conglobatus, 1 mM in DMSO, 0.2 μm filtered

Monensin sodium salt

90-95% (TLC)

Phorbol 12-myristate 13-acetate

≥99% (TLC), film or powder

Customers Also Viewed

Brefeldin A

≥99% (HPLC and TLC), BioXtra, for molecular biology

Brefeldin A

from Penicillium brefeldianum, Ready Made Solution, 10 mg/mL in DMSO, 0.2 μm filtered

Monensin sodium salt

90-95% (TLC)

Thapsigargin

≥98% (HPLC), solid film

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
22
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
GY8410000

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Alternatively activated macrophage-derived RELM-{alpha} is a negative regulator of type 2 inflammation in the lung. Nair MG J. Exp. Med. 206(4), 937-52, (2009)

Loading...


Obesity in psoriasis: leptin and resistin as mediators of cutaneous inflammation. A. Johnston et al Br. J. Dermatol. 159, 342-50, (2009)

Loading...


Relationship between functional profile of HIV-1 specific CD8 T cells and epitope variability with the selection of escape mutants in acute HIV-1 infection. Ferrari G, Korber B, Goonetilleke N, et al. PLoS Pathog. 7(2), e1001273, (2011)

Loading...


Golgicide A reveals essential roles for GBF1 in Golgi assembly and function. Sáenz, J.B., et al. Nat. Chem. Biol., (2009)

Loading...


Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

Loading...


Treatment-dependent loss of polyfunctional CD8+ T-cell responses in HIV-infected kidney transplant recipients is associated with herpesvirus reactivation. O Gasser et al Am. J. Transplant. 9, 794-803, (2009)

Loading...


Brefeldin A: deciphering an enigmatic inhibitor of secretion. Nebenführ A, Ritzenthaler C, and Robinson DG Plant Physiol. 130(3), 1102-8, (2002)

Loading...


Expanded breadth of the T-cell response to mosaic human immunodeficiency virus type 1 envelope DNA vaccination. Kong WP J. Virol. 83(5), 2201-15, (2009)

Loading...


High frequency, sustained T cell responses to PARV4 suggest viral persistence in vivo. Simmons R J. Infect. Dis. 203(10), 1378-87, (2011)

Loading...


Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

Loading...


Identifying off-target effects and hidden phenotypes of drugs in human cells. Marnie L MacDonald et al Nat. Chem. Biol. 2, 329-37, (2006)

Loading...


Early secreted antigen ESAT-6 of Mycobacterium tuberculosis promotes protective T helper 17 cell responses in a toll-like receptor-2-dependent manner. Samit Chatterjee et al PLoS Pathog. 7, e1002378, (2011)

Loading...


In vivo equilibrium of proinflammatory IL-17+ and regulatory IL-10+ Foxp3+ RORgamma t+ T cells. Lochner M J. Exp. Med. 205(6), 1381-93, (2008)

Loading...


Cationic lipid/DNA complexes (JVRS-100) combined with influenza vaccine (Fluzone) increases antibody response, cellular immunity, and antigenically drifted protection. Marla Lay et al Vaccine 27, 3811-20, (2009)

Loading...


αB-crystallin: a Golgi-associated membrane protein in the developing ocular lens. Rajendra K. Gangalum et al Invest. Ophthalmol. Vis. Sci. 50, 3283-90, (2010)

Loading...


A chemical study of cyclic depsipeptides produced by a sponge-derived fungus. Taro Amagata et al J. Nat. Prod. 69, 1560-5, (2006)

Loading...


Kinetics and phenotype of vaccine-induced CD8+ T-cell responses to Toxoplasma gondii. Jordan KA Infect. Immun. 77(9), 3894-901, (2009)

Loading...


CD11b⁺, Ly6G⁺ cells produce type I interferon and exhibit tissue protective properties following peripheral virus infection. Fischer MA, Davies ML, Reider IE, et al. PLoS Pathog. 7(11), e1002374, (2011)

Loading...


Polyfunctional CD4+ T-cell induction in neutralizing antibody-triggered control of simian immunodeficiency virus infection. Yamamoto T J. Virol. 83(11), 5514-24, (2009)

Loading...


D27-pLpxL, an avirulent strain of Yersinia pestis, primes T cells that protect against pneumonic plague. Frank M. Szaba et al Infect. Immun. 77, 4295-304, (2009)

Loading...


A Candida albicans petite mutant strain with uncoupled oxidative phosphorylation overexpresses MDR1 and has diminished susceptibility to fluconazole and voriconazole. Shaoji Cheng et al Antimicrob. Agents Chemother. 51, 1855-8, (2007)

Loading...


WFDC1/ps20 is a novel innate immunomodulatory signature protein of human immunodeficiency virus (HIV)-permissive CD4+ CD45RO+ memory T cells that promotes infection by upregulating CD54 integrin expression and is elevated in HIV type 1 infection. R. Alvarez et al J. Virol. 82, 471-86, (2008)

Loading...


Cellular players and role of selectin ligands in leukocyte recruitment in a T-cell-initiated delayed-type hypersensitivity reaction. Doebis C Am. J. Pathol. 173(4), 1067-76, (2008)

Loading...


Activation of the sphingomyelin cycle by brefeldin A: effects of brefeldin A on differentiation and implications for a role for ceramide in regulation of protein trafficking. Linardic, C.M., et al. Cell Growth Differ. 7, 765-774, (1996)

Loading...


Synthesis and anticancer activity of brefeldin A ester derivatives. Nwanne O Anadu et al J. Med. Chem. 49, 3897-905, (2006)

Loading...


Human interleukin 17-producing cells originate from a CD161+CD4+ T cell precursor. Cosmi L, De Palma R, Santarlasci V, et al. J. Exp. Med. 205(8), 1903-16, (2008)

Loading...


Brefeldin A effects in plant and fungal cells: something new about vesicle trafficking? Satiat-Jeunemaitre B, Cole L, Bourett T, et al. J. Microsc. 181(Pt 2), 162-77, (1996)

Loading...


LKB1 inactivation sensitizes non-small cell lung cancer to pharmacological aggravation of ER stress. Inge LJ, Friel JM, Richer AL, et al. Cancer Lett. 352(2), 187-95, (2014)

Loading...


GAD65-Specific Cytotoxic T Lymphocytes Mediate Beta-Cell Death and Loss of Function. Rasche S, Busick RY, and Quinn A Rev. Diabet. Stud. 6(1), 43-53, (2009)

Loading...


Brefeldin A and the endocytic pathway. Possible implications for membrane traffic and sorting. Hunziker W, Whitney JA, and Mellman I FEBS Lett. 307(1), 93-6, (1992)

Loading...


Brefeldin A revealing the fundamental principles governing membrane dynamics and protein transport. Jackson CL Subcell. Biochem. 34, 233-72, (2000)

Loading...


A CREB3-ARF4 signalling pathway mediates the response to Golgi stress and susceptibility to pathogens. Reiling JH, Olive AJ, Sanyal S, et al. Nat. Cell Biol. 15(12), 1473-85, (2013)

Loading...


Gain-of-function mutations in the transcription factor MRR1 are responsible for overexpression of the MDR1 efflux pump in fluconazole-resistant Candida dubliniensis strains. Sabrina Schubert et al Antimicrob. Agents Chemother. 52, 4274-80, (2008)

Loading...


TGF-β-induced Foxp3 inhibits T(H)17 cell differentiation by antagonizing RORγt function. Liang Zhou et al Nature 453, 236-40, (2008)

Loading...


Fission yeast SWI/SNF and RSC complexes show compositional and functional differences from budding yeast. Monahan BJ Nat. Struct. Mol. Biol. 15(8), 873-80, (2008)

Loading...


Impact on malaria parasite multiplication rates in infected volunteers of the protein-in-adjuvant vaccine AMA1-C1/Alhydrogel+CPG 7909. Duncan CJ, Sheehy SH, Ewer KJ, et al. PLoS ONE 6(7), e22271, (2011)

Loading...


Primary human immunodeficiency virus type 1-specific CD8+ T-cell responses induced by myeloid dendritic cells. Bonnie A. Colleton et al J. Virol. 83, 6288-99, (2009)

Loading...


Vaccinia viruses with mutations in the E3L gene as potential replication-competent, attenuated vaccines: scarification vaccination. Jentarra, GM Vaccine 26(23), 2860-72, (2008)

Loading...


Co-engagement of α(4)β(1) integrin (VLA-4) and CD4 or CD8 is necessary to induce maximal Erk1/2 phosphorylation and cytokine production in human T cells. Tae Kon Kim et al Hum. Immunol. 71, 23-8, (2009)

Loading...


Identification and characterization of IL-10/IFN-gamma-producing effector-like T cells with regulatory function in human blood. Häringer B, Lozza L, Steckel B, et al. J. Exp. Med. 206(5), 1009-17, (2009)

Loading...


Redundancy renders the glycoprotein 96 receptor scavenger receptor A dispensable for cross priming in vivo. Tewalt EF Immunology 125(4), 480-91, (2008)

Loading...


Brefeldin A: the advantage of being uncompetitive. Chardin P and McCormick F Cell 97(2), 153-5, (1999)

Loading...


Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,). George R Pettit et al J. Nat. Prod. 71, 438-44, (2008)

Loading...


Age-dependent susceptibility to a viral disease due to decreased natural killer cell numbers and trafficking. Fang M J. Exp. Med. 207(11), 2369-81, (2010)

Loading...


Minocycline inhibition of monocyte activation correlates with neuronal protection in SIV neuroAIDS. Jennifer H. Campbell et al PLoS ONE 6, e18688, (2011)

Loading...


Chemical biology studies on norrisolide. Gianni Guizzunti et al Bioorg. Med. Chem. 18, 2115-22, (2010)

Loading...


Vaccination against heterologous R5 clade C SHIV: prevention of infection and correlates of protection. Lakhashe SK, Wang W, Siddappa NB, et al. PLoS ONE 6(7), e22010, (2011)

Loading...


Analysis of IL-17(+) cells in facet joints of patients with spondyloarthritis suggests that the innate immune pathway might be of greater relevance than the Th17-mediated adaptive immune response. Appel H, Maier R, Wu P, et al. Arthritis. Res. Ther. 13(3), R95, (2011)

Loading...


Small-molecule synergist of the Wnt/beta-catenin signaling pathway Zhang, Q. et al. Proc. Natl. Acad. Sci. U. S. A. 104, 7444-7448, (2007)

Loading...


Phenotype changes and impaired function of dendritic cell subsets in patients with sepsis: a prospective observational analysis. Poehlmann H Critical Care 13(4), R119, (2009)

Loading...


Impaired CD4 T cell memory response to Streptococcus pneumoniae precedes CD4 T cell depletion in HIV-infected Malawian adults. Glennie SJ, Sepako E, Mzinza D, et al. PLoS ONE 6(9), e25610, (2011)

Loading...


CD4 T cell immunity is critical for the control of simian varicella virus infection in a nonhuman primate model of VZV infection. Haberthur K, Engelmann F, Park B, et al. PLoS Pathog. 7(11), e1002367, (2011)

Loading...


Unmodified self antigen triggers human CD8 T cells with stronger tumor reactivity than altered antigen. Speiser DE Proc. Natl. Acad. Sci. U. S. A. 105(10), 3849-54, (2008)

Loading...


Recruitment of the Mint3 adaptor is necessary for export of the amyloid precursor protein (APP) from the Golgi complex. Caster AH and Kahn RA J. Biol. Chem. 288(40), 28567-80, (2013)

Loading...


Brefeldin A-mediated apoptosis requires the activation of caspases and is inhibited by Bcl-2. Guo, H., et al. Exp. Cell Res. 245, 57, (1998)

Loading...


Golgi-disturbing agents. Dinter, A. and Berger, E.G. Histochem. Cell Biol. 109, 571-590, (1998)

Loading...


Brefeldin A is a potent inducer of apoptosis in human cancer cells independently of p53. Shao, R.G., et al. Exp. Cell Res. 227, 190-196, (1996)

Loading...


Multiple T-cell responses to human immunodeficiency virus type 1 are enhanced by dendritic cells. Huang XL, Fan Z, Borowski L, et al. Clin. Vaccine Immunol. 16(10), 1504-16, (2009)

Loading...


The CD8 T-cell response against murine gammaherpesvirus 68 is directed toward a broad repertoire of epitopes from both early and late antigens. Gredmark-Russ S J. Virol. 82(24), 12205-12, (2008)

Loading...


Apoptotic cells induce dendritic cell-mediated suppression via interferon-γ-induced IDO. Charlotte A Williams et al Immunology 124, 89-101, (2008)

Loading...


Rapid stimulation of human renal ENaC by cAMP in Xenopus laevis oocytes. Robins GG, MacLennan KA, Boot-Handford RP, et al. J. Physiol. Biochem. 69(3), 419-27, (2013)

Loading...


Breast cancer: coordinated regulation of CCL2 secretion by intracellular glycosaminoglycans and chemokine motifs. Lebel-Haziv Y, Meshel T, Soria G, et al. Neoplasia 16(9), 723-40, (2014)

Loading...


Negative feedback regulation of T cells via interleukin-2 and FOXP3 reciprocity. Popmihajlov Z PLoS ONE 3(2), e1581, (2008)

Loading...


SAAG-4 is a novel mosquito salivary protein that programmes host CD4 T cells to express IL-4. Boppana VD Parasite Immunol. 31(6), 287-95, (2009)

Loading...


The effect of single and combined activating killer immunoglobulin-like receptor genotypes on cytomegalovirus infection and immunity after hematopoietic cell transplantation. Zaia JA Biol. Blood Marrow Transplant. 15(3), 315-25, (2009)

Loading...


Characterization of regulatory T cells identified as CD4(+)CD25(high)CD39(+) in patients with active tuberculosis. T Chiacchio et al Clin. Exp. Immunol. 156, 463-70, (2009)

Loading...


Association Of The Cellular Coactivator HCF-1 With The Golgi Apparatus In Sensory Neurons. Kolb, G., and Kristie, T.M. J. Virol. Meth. 82, 9555-63, (2008)

Loading...


Arf, Sec7 and Brefeldin A: a model towards the therapeutic inhibition of guanine nucleotide-exchange factors. Zeghouf M, Guibert B, Zeeh JC, et al. Biochem. Soc. Trans. 33(Pt 6), 1265-8, (2005)

Loading...


Histamine induces ATP release from human subcutaneous fibroblasts, via pannexin-1 hemichannels, leading to Ca2+ mobilization and cell proliferation. Pinheiro AR, Paramos-de-Carvalho D, Certal M, et al. J. Biol. Chem. 288(38), 27571-83, (2013)

Loading...


CAF01 potentiates immune responses and efficacy of an inactivated influenza vaccine in ferrets. Cyril Jean-Marie Martel et al PLoS ONE 6, e22891, (2011)

Loading...


Inhibition of ADP-ribosylation suppresses aberrant accumulation of lipidated apolipoprotein B in the endoplasmic reticulum. Ohsaki Y, Cheng J, Yamairi K, et al. FEBS Lett. 587(22), 3696-702, (2013)

Loading...


Structure-based discovery of an inhibitor of Arf activation by Sec7 domains through targeting of protein-protein complexes. Julien Viaud et al Proc. Natl. Acad. Sci. U. S. A. 104, 10370-5, (2007)

Loading...


Brefeldin A: insights into the control of membrane traffic and organelle structure. Klausner RD, Donaldson JG, and Lippincott-Schwartz J J. Cell Biol. 116(5), 1071-80, (1992)

Loading...


Glutamine deprivation stimulates mTOR-JNK-dependent chemokine secretion. Shanware NP, Bray K, Eng CH, et al. Nat. Commun. 5, 4900, (2014)

Loading...


Multiple targets for brefeldin A. Pelham HR Cell 67(3), 449-51, (1991)

Loading...


Polarized axonal surface expression of neuronal KCNQ potassium channels is regulated by calmodulin interaction with KCNQ2 subunit. Cavaretta JP, Sherer KR, Lee KY, et al. PLoS ONE 9(7), e103655, (2014)

Loading...


Attenuation of immune-mediated influenza pneumonia by targeting the inducible co-stimulator (ICOS) molecule on T cells. Sakthivel P, Gereke M, Breithaupt A, et al. PLoS ONE 9(7), e100970, (2014)

Loading...


Evaluation of T cell responses in healing and nonhealing leishmaniasis reveals differences in T helper cell polarization ex vivo and in vitro. Choi BS Parasite Immunol. 31(4), 199-209, (2009)

Loading...


The human cancer antigen mesothelin is more efficiently presented to the mouse immune system when targeted to the DEC-205/CD205 receptor on dendritic cells. Wang B Ann. N. Y. Acad. Sci. 1174, 6-17, (2009)

Loading...


Increased programmed death-1 molecule expression in cytomegalovirus disease and acute graft-versus-host disease after allogeneic hematopoietic cell transplantation. Gallez-Hawkins GM, Thao L, Palmer J, et al. Biol. Blood Marrow Transplant. 15(7), 872-80, (2009)

Loading...


Immunization with an immunodominant self-peptide derived from glucose-6-phosphate isomerase induces arthritis in DBA/1 mice. Bruns L Arthritis. Res. Ther. 11(4), R117, (2009)

Loading...


Toll-like receptor 2 dependent immunogenicity of glycoconjugate vaccines containing chemically derived zwitterionic polysaccharides. Gallorini S Proc. Natl. Acad. Sci. U. S. A. 106(41), 17481-6, (2009)

Loading...


Biological effects of the antibiotic brefeldin A (decumbin, cyanein, ascotoxin, synergisidin): a retrospective. Betina V Folia Microbiol. (Praha) 37(1), 3-11, (1992)

Loading...


Circulating and tumor-infiltrating Foxp3⁺ regulatory T cell subset in Chinese patients with extranodal NK/T cell lymphoma. Peng RJ, Huang ZF, Zhang YL, et al. Int. J. Biol. Sci. 7(7), 1027-36, (2011)

Loading...


Modulation of in vivo IgG crystallization in the secretory pathway by heavy chain isotype class switching and N-linked glycosylation. Hasegawa H, Forte C, Barber I, et al. Biochim. Biophys. Acta 1843(7), 1325-38, (2014)

Loading...


Merck 14,1369

Beil. 18,IV,1220

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?