Golgicide A

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MedKoo CAT#: 555903

CAS#: 1139889-93-2

Description: Golgicide A is a Potent, selective and reversible inhibitor of GBF1 ArfGEF. Golgicide A inhibited HSV-1 entry via beta-galactosidase reporter assay and impaired incoming virus transport to the nuclear periphery. Inhibition of GBF1 via golgicide A can result in rapid dissociation of COPI vesicle coat protein from Golgi membranes and disassembly of the Golgi and trans-Golgi network

Chemical Structure

Golgicide A
CAS# 1139889-93-2

Theoretical Analysis

MedKoo Cat#: 555903
Name: Golgicide A
CAS#: 1139889-93-2
Chemical Formula: C17H14F2N2
Exact Mass: 284.1125
Molecular Weight: 284.3098
Elemental Analysis: C, 71.82; H, 4.96; F, 13.36; N, 9.85

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 2 Weeks
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
200.0mg USD 1350.0 Ready to ship
500.0mg USD 2650.0 Ready to ship
1.0g USD 3850.0 2 Weeks
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Synonym: Golgicide A; GCA;

IUPAC/Chemical Name: (3aR,9bS)-6,8-difluoro-4-(pyridin-3-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline


InChi Code: InChI=1S/C17H14F2N2/c18-11-7-14-12-4-1-5-13(12)16(10-3-2-6-20-9-10)21-17(14)15(19)8-11/h1-4,6-9,12-13,16,21H,5H2/t12-,13+,16?/m0/s1

SMILES Code: FC4=CC([C@]3([H])[C@]([H])2CC=C3)=C(C(F)=C4)NC2C1=CN=CC=C1

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

Biological target: Golgicide A (GCA) is a potent, highly specific, and reversible inhibitor of the cis-Golgi ADP-ribosylation factor guanine nucleotide exchange factors (ArfGEF) GBF1.
In vitro activity: The effect of GCA on toxin trafficking and on intracellular organelle morphology was examined. Immunofluoresence experiments demonstrated dramatic effects of GCA on the Golgi and TGN. Whereas the Golgi remains as a tightly organized perinuclear ribbon in untreated cells, GCA caused complete dispersal of the medial-Golgi markers giantin and the cis-Golgi marker GM130. Treatment with GCA resulted in a diffuse and punctate distribution of the medial-Golgi marker giantin. The punctate structures were in contact with Sec31-positive foci, indicative of their association with ER exit sites. GCA also caused the TGN to disperse into small vesicles that subsequently disseminated throughout the cell. Reference: Nat Chem Biol. 2009 Mar;5(3):157-65. https://pubmed.ncbi.nlm.nih.gov/19182783/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 45.3 159.34

Preparing Stock Solutions

The following data is based on the product molecular weight 284.3098 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. van der Linden L, van der Schaar HM, Lanke KH, Neyts J, van Kuppeveld FJ. Differential effects of the putative GBF1 inhibitors Golgicide A and AG1478 on enterovirus replication. J Virol. 2010 Aug;84(15):7535-42. doi: 10.1128/JVI.02684-09. Epub 2010 May 26. PMID: 20504936; PMCID: PMC2897619. 2. Sáenz JB, Sun WJ, Chang JW, Li J, Bursulaya B, Gray NS, Haslam DB. Golgicide A reveals essential roles for GBF1 in Golgi assembly and function. Nat Chem Biol. 2009 Mar;5(3):157-65. doi: 10.1038/nchembio.144. Epub 2009 Feb 1. PMID: 19182783; PMCID: PMC3500152.
In vitro protocol: 1. van der Linden L, van der Schaar HM, Lanke KH, Neyts J, van Kuppeveld FJ. Differential effects of the putative GBF1 inhibitors Golgicide A and AG1478 on enterovirus replication. J Virol. 2010 Aug;84(15):7535-42. doi: 10.1128/JVI.02684-09. Epub 2010 May 26. PMID: 20504936; PMCID: PMC2897619. 2. Sáenz JB, Sun WJ, Chang JW, Li J, Bursulaya B, Gray NS, Haslam DB. Golgicide A reveals essential roles for GBF1 in Golgi assembly and function. Nat Chem Biol. 2009 Mar;5(3):157-65. doi: 10.1038/nchembio.144. Epub 2009 Feb 1. PMID: 19182783; PMCID: PMC3500152.
In vivo protocol: TBD

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Additional Information

1: Tebaldi G, Pritchard SM, Nicola AV. Herpes Simplex Virus Entry by a Nonconventional Endocytic Pathway. J Virol. 2020 Nov 23;94(24):e01910-20. doi: 10.1128/JVI.01910-20. PMID: 33028710.

2: Bäck N, Luxmi R, Powers KG, Mains RE, Eipper BA. Peptidylglycine α-amidating monooxygenase is required for atrial secretory granule formation. Proc Natl Acad Sci U S A. 2020 Jul 28;117(30):17820-17831. doi: 10.1073/pnas.2004410117. Epub 2020 Jul 13. PMID: 32661174; PMCID: PMC7395455.

3: Zhang L, Wang T, Song M, Jin M, Liu S, Guo K, Zhang Y. Rab1b-GBF1-ARFs mediated intracellular trafficking is required for classical swine fever virus replication in swine umbilical vein endothelial cells. Vet Microbiol. 2020 Jul;246:108743. doi: 10.1016/j.vetmic.2020.108743. Epub 2020 Jun 1. PMID: 32605744.

4: Uckeley ZM, Moeller R, Kühn LI, Nilsson E, Robens C, Lasswitz L, Lindqvist R, Lenman A, Passos V, Voss Y, Sommerauer C, Kampmann M, Goffinet C, Meissner F, Överby AK, Lozach PY, Gerold G. Quantitative Proteomics of Uukuniemi Virus-host Cell Interactions Reveals GBF1 as Proviral Host Factor for Phleboviruses. Mol Cell Proteomics. 2019 Dec;18(12):2401-2417. doi: 10.1074/mcp.RA119.001631. Epub 2019 Sep 30. PMID: 31570497; PMCID: PMC6885706.

5: Martínez JL, Arnoldi F, Schraner EM, Eichwald C, Silva-Ayala D, Lee E, Sztul E, Burrone ÓR, López S, Arias CF. The Guanine Nucleotide Exchange Factor GBF1 Participates in Rotavirus Replication. J Virol. 2019 Sep 12;93(19):e01062-19. doi: 10.1128/JVI.01062-19. PMID: 31270230; PMCID: PMC6744240.

6: Alborzinia H, Ignashkova TI, Dejure FR, Gendarme M, Theobald J, Wölfl S, Lindemann RK, Reiling JH. Golgi stress mediates redox imbalance and ferroptosis in human cells. Commun Biol. 2018 Nov 28;1:210. doi: 10.1038/s42003-018-0212-6. PMID: 30511023; PMCID: PMC6262011.

7: Rosales Ramirez R, Ludert JE. The Dengue Virus Nonstructural Protein 1 (NS1) Is Secreted from Mosquito Cells in Association with the Intracellular Cholesterol Transporter Chaperone Caveolin Complex. J Virol. 2019 Feb 5;93(4):e01985-18. doi: 10.1128/JVI.01985-18. PMID: 30463973; PMCID: PMC6364000.

8: Walch L, Pellier E, Leng W, Lakisic G, Gautreau A, Contremoulins V, Verbavatz JM, Jackson CL. GBF1 and Arf1 interact with Miro and regulate mitochondrial positioning within cells. Sci Rep. 2018 Nov 20;8(1):17121. doi: 10.1038/s41598-018-35190-0. PMID: 30459446; PMCID: PMC6244289.

9: Ferlin J, Farhat R, Belouzard S, Cocquerel L, Bertin A, Hober D, Dubuisson J, Rouillé Y. Investigation of the role of GBF1 in the replication of positive- sense single-stranded RNA viruses. J Gen Virol. 2018 Aug;99(8):1086-1096. doi: 10.1099/jgv.0.001099. Epub 2018 Jun 20. PMID: 29923822.

10: Shen SM, Ji Y, Zhang C, Dong SS, Yang S, Xiong Z, Ge MK, Yu Y, Xia L, Guo M, Cheng JK, Liu JL, Yu JX, Chen GQ. Nuclear PTEN safeguards pre-mRNA splicing to link Golgi apparatus for its tumor suppressive role. Nat Commun. 2018 Jun 19;9(1):2392. doi: 10.1038/s41467-018-04760-1. PMID: 29921876; PMCID: PMC6008332.

11: Banerjee S, Aponte-Diaz D, Yeager C, Sharma SD, Ning G, Oh HS, Han Q, Umeda M, Hara Y, Wang RYL, Cameron CE. Hijacking of multiple phospholipid biosynthetic pathways and induction of membrane biogenesis by a picornaviral 3CD protein. PLoS Pathog. 2018 May 21;14(5):e1007086. doi: 10.1371/journal.ppat.1007086. PMID: 29782554; PMCID: PMC5983871.

12: Luchsinger C, Aguilar M, Burgos PV, Ehrenfeld P, Mardones GA. Functional disruption of the Golgi apparatus protein ARF1 sensitizes MDA-MB-231 breast cancer cells to the antitumor drugs Actinomycin D and Vinblastine through ERK and AKT signaling. PLoS One. 2018 Apr 3;13(4):e0195401. doi: 10.1371/journal.pone.0195401. PMID: 29614107; PMCID: PMC5882166.

13: Baumann J, Ignashkova TI, Chirasani SR, Ramírez-Peinado S, Alborzinia H, Gendarme M, Kuhnigk K, Kramer V, Lindemann RK, Reiling JH. Golgi stress-induced transcriptional changes mediated by MAPK signaling and three ETS transcription factors regulate MCL1 splicing. Mol Biol Cell. 2018 Jan 1;29(1):42-52. doi: 10.1091/mbc.E17-06-0418. Epub 2017 Nov 8. PMID: 29118074; PMCID: PMC5746065.

14: Farhat R, Ankavay M, Lebsir N, Gouttenoire J, Jackson CL, Wychowski C, Moradpour D, Dubuisson J, Rouillé Y, Cocquerel L. Identification of GBF1 as a cellular factor required for hepatitis E virus RNA replication. Cell Microbiol. 2018 Jan;20(1):e12804. doi: 10.1111/cmi.12804. Epub 2017 Nov 17. PMID: 29112323; PMCID: PMC7162332.

15: Gendarme M, Baumann J, Ignashkova TI, Lindemann RK, Reiling JH. Image-based drug screen identifies HDAC inhibitors as novel Golgi disruptors synergizing with JQ1. Mol Biol Cell. 2017 Dec 15;28(26):3756-3772. doi: 10.1091/mbc.E17-03-0176. Epub 2017 Oct 26. PMID: 29074567; PMCID: PMC5739293.

16: Wang J, Fresquez T, Kandachar V, Deretic D. The Arf GEF GBF1 and Arf4 synergize with the sensory receptor cargo, rhodopsin, to regulate ciliary membrane trafficking. J Cell Sci. 2017 Dec 1;130(23):3975-3987. doi: 10.1242/jcs.205492. Epub 2017 Oct 12. PMID: 29025970; PMCID: PMC5769590.

17: Zhang N, Zhang L. Key components of COPI and COPII machineries are required for chikungunya virus replication. Biochem Biophys Res Commun. 2017 Nov 25;493(3):1190-1196. doi: 10.1016/j.bbrc.2017.09.142. Epub 2017 Sep 28. PMID: 28962860.

18: Ignashkova TI, Gendarme M, Peschk K, Eggenweiler HM, Lindemann RK, Reiling JH. Cell survival and protein secretion associated with Golgi integrity in response to Golgi stress-inducing agents. Traffic. 2017 Aug;18(8):530-544. doi: 10.1111/tra.12493. Epub 2017 Jun 30. PMID: 28485883.

19: Liang W, Zheng M, Bao C, Zhang Y. CSFV proliferation is associated with GBF1 and Rab2. J Biosci. 2017 Mar;42(1):43-56. doi: 10.1007/s12038-016-9659-0. PMID: 28229964; PMCID: PMC7091326.

20: Vázquez-Calvo Á, Caridi F, González-Magaldi M, Saiz JC, Sobrino F, Martín- Acebes MA. The Amino Acid Substitution Q65H in the 2C Protein of Swine Vesicular Disease Virus Confers Resistance to Golgi Disrupting Drugs. Front Microbiol. 2016 Apr 27;7:612. doi: 10.3389/fmicb.2016.00612. PMID: 27199941; PMCID: PMC4846857.