Acivicin
featured

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

MedKoo CAT#: 524131

CAS#: 42228-92-2

Description: Acivicin is an inhibitor of gamma-glutamyl transferase. It is a potent antineoplastic agent. Acivicin interferes with glutamate metabolism and inhibits glutamate dependent synthesis of enzymes, and is thereby potentially helpful in treatment of solid tumors.


Price and Availability

Size
Price

5mg
USD 250
Size
Price

10mg
USD 450
Size
Price

20mg
USD 750

Acivicin, 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

img

Theoretical Analysis

MedKoo Cat#: 524131
Name: Acivicin
CAS#: 42228-92-2
Chemical Formula: C5H7ClN2O3
Exact Mass: 178.01452
Molecular Weight: 178.57
Elemental Analysis: C, 33.63; H, 3.95; Cl, 19.85; N, 15.69; O, 26.88


Synonym: Acivicin; Antibiotic AT-125; NSC 163501; U 42126;

IUPAC/Chemical Name: (2S)-Amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]ethanoic acid

InChi Key: QAWIHIJWNYOLBE-OKKQSCSOSA-N

InChi Code: InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1

SMILES Code: O=C(O)[C@@H](N)[C@@H]1CC(Cl)=NO1


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, not in water

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:
293490


References

1: Li L, Shi W, Wu X, Gong Q, Li X, Ma H. Monitoring γ-glutamyl transpeptidase activity and evaluating its inhibitors by a water-soluble near-infrared fluorescent probe. Biosens Bioelectron. 2016 Jul 15;81:395-400. doi: 10.1016/j.bios.2016.03.021. Epub 2016 Mar 12. PubMed PMID: 26995285.

2: Pinto A, Tamborini L, Cullia G, Conti P, De Micheli C. Inspired by Nature: The 3-Halo-4,5-dihydroisoxazole Moiety as a Novel Molecular Warhead for the Design of Covalent Inhibitors. ChemMedChem. 2016 Jan;11(1):10-4. doi: 10.1002/cmdc.201500496. Epub 2015 Nov 26. PubMed PMID: 26607551.

3: Shalom G, Zisman D, Bitterman H, Harman-Boehm I, Greenberg-Dotan S, Dreiher J, Feldhamer I, Moser H, Hammerman A, Cohen Y, Cohen AD. Systemic Therapy for Psoriasis and the Risk of Herpes Zoster: A 500,000 Person-year Study. JAMA Dermatol. 2015 May;151(5):533-8. doi: 10.1001/jamadermatol.2014.4956. PubMed PMID: 25797026.

4: Kreuzer J, Bach NC, Forler D, Sieber SA. Target discovery of acivicin in cancer cells elucidates its mechanism of growth inhibition†Electronic supplementary information (ESI) available: Synthesis, cloning, protein expression, purification and biochemical assays. See DOI: 10.1039/c4sc02339k. Chem Sci. 2014 Dec 1;6(1):237-245. Epub 2014 Sep 26. PubMed PMID: 25580214; PubMed Central PMCID: PMC4285139.

5: Sinha S, Ahire D, Wagh S, Mullick D, Sistla R, Selvakumar K, Cortes JC, Putlur SP, Mandlekar S, Johnson BM. Electrophilicity of pyridazine-3-carbonitrile, pyrimidine-2-carbonitrile, and pyridine-carbonitrile derivatives: a chemical model to describe the formation of thiazoline derivatives in human liver microsomes. Chem Res Toxicol. 2014 Dec 15;27(12):2052-61. doi: 10.1021/tx500256j. Epub 2014 Dec 2. PubMed PMID: 25372409.

6: Tuzova M, Jean JC, Hughey RP, Brown LA, Cruikshank WW, Hiratake J, Joyce-Brady M. Inhibiting lung lining fluid glutathione metabolism with GGsTop as a novel treatment for asthma. Front Pharmacol. 2014 Jul 31;5:179. doi: 10.3389/fphar.2014.00179. eCollection 2014. PubMed PMID: 25132819; PubMed Central PMCID: PMC4116799.

7: Mathieu C, González Salgado A, Wirdnam C, Meier S, Grotemeyer MS, Inbar E, Mäser P, Zilberstein D, Sigel E, Bütikofer P, Rentsch D. Trypanosoma brucei eflornithine transporter AAT6 is a low-affinity low-selective transporter for neutral amino acids. Biochem J. 2014 Oct 1;463(1):9-18. doi: 10.1042/BJ20140719. PubMed PMID: 24988048.

8: Maeda K, Nakajima Y, Motoyama T, Kitou Y, Kosaki T, Saito T, Nishiuchi T, Kanamaru K, Osada H, Kobayashi T, Kimura M. Effects of acivicin on growth, mycotoxin production and virulence of phytopathogenic fungi. Lett Appl Microbiol. 2014 Oct;59(4):377-83. doi: 10.1111/lam.12289. Epub 2014 Jun 19. PubMed PMID: 24863673.

9: Scicinski J, Oronsky B, Cooper V, Taylor M, Alexander M, Hadar R, Cosford R, Fleischmann T, Fitch WL. Development of methods for the bioanalysis of RRx-001 and metabolites. Bioanalysis. 2014 Apr;6(7):947-56. doi: 10.4155/bio.13.331. PubMed PMID: 24806903.

10: Ida T, Suzuki H, Fukuyama K, Hiratake J, Wada K. Structure of Bacillus subtilis γ-glutamyltranspeptidase in complex with acivicin: diversity of the binding mode of a classical and electrophilic active-site-directed glutamate analogue. Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):607-14. doi: 10.1107/S1399004713031222. Epub 2014 Jan 31. PubMed PMID: 24531494; PubMed Central PMCID: PMC3940202.

11: Rosa JM, Dafre AL, Rodrigues AL. Antidepressant-like responses in the forced swimming test elicited by glutathione and redox modulation. Behav Brain Res. 2013 Sep 15;253:165-72. doi: 10.1016/j.bbr.2013.07.009. Epub 2013 Jul 11. PubMed PMID: 23850355.

12: Ki MR, Yun NR, Hwang SY. Glutamine-induced production and secretion of Helicobacter pylori gamma-glutamyltranspeptidase at low pH and its putative role in glutathione transport. J Microbiol Biotechnol. 2013 Apr;23(4):467-72. PubMed PMID: 23568200.

13: Stephan J, Franke J, Ehrenhofer-Murray AE. Chemical genetic screen in fission yeast reveals roles for vacuolar acidification, mitochondrial fission, and cellular GMP levels in lifespan extension. Aging Cell. 2013 Aug;12(4):574-83. doi: 10.1111/acel.12077. Epub 2013 Apr 23. PubMed PMID: 23521895.

14: Geier EG, Schlessinger A, Fan H, Gable JE, Irwin JJ, Sali A, Giacomini KM. Structure-based ligand discovery for the Large-neutral Amino Acid Transporter 1, LAT-1. Proc Natl Acad Sci U S A. 2013 Apr 2;110(14):5480-5. doi: 10.1073/pnas.1218165110. Epub 2013 Mar 18. PubMed PMID: 23509259; PubMed Central PMCID: PMC3619328.

15: Willoughby LF, Schlosser T, Manning SA, Parisot JP, Street IP, Richardson HE, Humbert PO, Brumby AM. An in vivo large-scale chemical screening platform using Drosophila for anti-cancer drug discovery. Dis Model Mech. 2013 Mar;6(2):521-9. doi: 10.1242/dmm.009985. Epub 2012 Sep 20. PubMed PMID: 22996645; PubMed Central PMCID: PMC3597034.

16: Dahboul F, Leroy P, Maguin Gate K, Boudier A, Gaucher C, Liminana P, Lartaud I, Pompella A, Perrin-Sarrado C. Endothelial γ-glutamyltransferase contributes to the vasorelaxant effect of S-nitrosoglutathione in rat aorta. PLoS One. 2012;7(9):e43190. doi: 10.1371/journal.pone.0043190. Epub 2012 Sep 11. PubMed PMID: 22984412; PubMed Central PMCID: PMC3439434.

17: Tamborini L, Pinto A, Smith TK, Major LL, Iannuzzi MC, Cosconati S, Marinelli L, Novellino E, Lo Presti L, Wong PE, Barrett MP, De Micheli C, Conti P. Synthesis and biological evaluation of CTP synthetase inhibitors as potential agents for the treatment of African trypanosomiasis. ChemMedChem. 2012 Sep;7(9):1623-34. doi: 10.1002/cmdc.201200304. Epub 2012 Aug 2. PubMed PMID: 22865834; PubMed Central PMCID: PMC3744939.

18: Wang Y, Zalups RK, Barfuss DW. Luminal transport of thiol S-conjugates of methylmercury in isolated perfused rabbit renal proximal tubules. Toxicol Lett. 2012 Sep 3;213(2):203-10. doi: 10.1016/j.toxlet.2012.07.003. Epub 2012 Jul 16. PubMed PMID: 22800651; PubMed Central PMCID: PMC3423585.

19: Yoshida T, Nasu H, Namba E, Ubukata O, Yamashita M. Discovery of a compound that acts as a bacterial PyrG (CTP synthase) inhibitor. J Med Microbiol. 2012 Sep;61(Pt 9):1280-5. doi: 10.1099/jmm.0.046052-0. Epub 2012 Jun 14. PubMed PMID: 22700553.

20: Kwiecień I, Iciek M, Włodek L. Acceleration of anaerobic cysteine transformations to sulfane sulfur consequent to γ-glutamyl transpeptidase inhibition. ScientificWorldJournal. 2012;2012:253724. doi: 10.1100/2012/253724. Epub 2012 Apr 30. PubMed PMID: 22629124; PubMed Central PMCID: PMC3353287.