Acivicin - CAS 42228-92-2
Not Intended for Therapeutic Use. For research use only.
Product Name:
Catalog Number:
CAS Number:
Acivicin is a glutamine analog that irreversibly inhibits glutamine-dependent amidotransferases involved in nucleotide and amino acid biosynthesis (Kis = 10 and 560 μM for anthranilate synthase and glutamate synthase, respectively) as a potent antitumor antibiotic that induces apoptosis in human lymphoblastoid cells.
Molecular Weight:
Molecular Formula:
Quality Standard:
Enterprise standard
Canonical SMILES:
Current Developer:
Chemical Structure
CAS 42228-92-2 Acivicin

Related Products

(CAS: 172430-48-7)

CVT-3369, a piperazineacetic acid derivative, is probably effective in some of biological studies.

CAS 220201-34-3 Talaporfin sodium

Talaporfin sodium
(CAS: 220201-34-3)

Talaporfin sodium is a natural chlorophyll-based, and water soluble PDT photosensitizer consisting of chlorin e6, derived from chlorophyll, and L-aspartic acid...

(CAS: 1311982-88-3)

MIR96-IN-1, a benzimidazole derivative, could restrain microRNA-96 biogenesis and also be probable to lead to the apoptosis of cancer cells.

CAS 67416-61-9 AKBA

(CAS: 67416-61-9)

AKBA is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator.

CAS 135383-60-7 (S)-Dolaphenine hydrochloride

(S)-Dolaphenine hydrochloride
(CAS: 135383-60-7)

(S)-Dolaphenine hydrochloride is a useful componet for compound synthesis.

CAS 471-66-9 Boswellic acid

Boswellic acid
(CAS: 471-66-9)

α-Boswellic acid is the principal constitutents of frankincense (olibanum). It is a specific, nonredox inhibitor of 5-lipoxygenase used to treat inflammation.

CAS 26833-87-4 Homoharringtonine

(CAS: 26833-87-4)

Protein synthesis inhibitor. Selective 60S ribosome inhibitor. Prevents substrate binding to the acceptor site on the 60S ribosome subunit. Inhibits elongation ...

(CAS: 1338545-07-5)

OTS-964, a thienoquinolin derivative, is a TOPK inhibitor and prabably be useful in studying anticancer agent as an analogue of OTS-514. It is still under precl...

CAS 58186-27-9 Idebenone

(CAS: 58186-27-9)

Idebenone is a synthetic analog of coenzyme Q10 (CoQ10) and a brain stimulant.

CAS 122555-91-3 DO3A tert-Butyl ester

DO3A tert-Butyl ester
(CAS: 122555-91-3)

DOTA tert-Butyl ester is a benxyl derivative of the cyclic tosamide; can be nitrated directly; is more convenient to incorporate the nitro group after deprotect...

CAS 76494-51-4 Ligustrazine Hydrochloride

Ligustrazine Hydrochloride
(CAS: 76494-51-4)

Ligustrazine Hydrochloride is a natural product extracted from the rhizomes of Ligusticum chuanxiong Hort. It displayed a protection effect on injured ECV304 ce...

CBR 5884
(CAS: 681159-27-3)

CBR 5884 is a 3-Phosphoglycerate dehydrogenase (PHGDH) inhibitor (IC50 = 33 μM), does not affect other NAD+-dependent dehydrogenases.

CAS 406-90-6 Flurossene

(CAS: 406-90-6)

Fluroxene is a volatile, inhalational anesthetic, and was the first halogenated hydrocarbon anesthetic to be introduced.

CAS 587-63-3 Dihydrokavain

(CAS: 587-63-3)

Dihydrokavain is a kavalactone source from kava beverages used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

(CAS: 391920-32-4)

Lubabegron is a β3-adrenoreceptor agonist.

CAS 4350-09-8 L-5-Hydroxytryptophan

(CAS: 4350-09-8)

L-5-Hydroxytryptophan is an intermediate in the biosynthesis of serotonin from tryptophan.

Bethanidine Sulfate
(CAS: 114-85-2)

This active molecular is a guanidinium antihypertensive agent through adrenergic neuron-blocking.

(CAS: 1262414-04-9)

Cenerimod is an active Lysosphingolipid receptor agonist originated by Actelion Pharmaceuticals and EC50 value is 2.7 nM. It is a S1P1/EDG1 receptor agonist and...

CAS 452-35-7 Ethoxzolamide

(CAS: 452-35-7)

Ethoxzolamide is used in the treatment of glaucoma, and is also used as a diuretic, acting as a carbonic anhydrase inhibitor.

CAS 39011-90-0 Albiflorin

(CAS: 39011-90-0)

Albiflorin is a major constituent presents in peony root, which possesses therapeutic potential for neurodegenerative diseases.

Reference Reading

1.Target discovery of acivicin in cancer cells elucidates its mechanism of growth inhibition†Electronic supplementary information (ESI) available: Synthesis, cloning, protein expression, purification
Kreuzer J1, Bach NC1, Forler D2, Sieber SA1. Chem Sci. 2014 Dec 1;6(1):237-245. Epub 2014 Sep 26.
Acivicin is a natural product with diverse biological activities. Several decades ago its clinical application in cancer treatment was explored but failed due to unacceptable toxicity. The causes behind the desired and undesired biological effects have never been elucidated and only limited information about acivicin-specific targets is available. In order to elucidate the target spectrum of acivicin in more detail we prepared functionalized derivatives and applied them for activity based proteomic profiling (ABPP) in intact cancer cells. Target deconvolution by quantitative mass spectrometry (MS) revealed a preference for specific aldehyde dehydrogenases. Further in depth target validation confirmed that acivicin inhibits ALDH4A1 activity by binding to the catalytic site. In accordance with this, downregulation of ALDH4A1 by siRNA resulted in a severe inhibition of cell growth and might thus provide an explanation for the cytotoxic effects of acivicin.
2.Inhibiting lung lining fluid glutathione metabolism with GGsTop as a novel treatment for asthma.
Tuzova M1, Jean JC1, Hughey RP2, Brown LA3, Cruikshank WW1, Hiratake J4, Joyce-Brady M1. Front Pharmacol. 2014 Jul 31;5:179. doi: 10.3389/fphar.2014.00179. eCollection 2014.
Asthma is characterized by airway inflammation. Inflammation is associated with oxidant stress. Airway epithelial cells are shielded from this stress by a thin layer of lung lining fluid (LLF) which contains an abundance of the antioxidant glutathione. LLF glutathione metabolism is regulated by γ-glutamyl transferase (GGT). Loss of LLF GGT activity in the mutant GGT(enu1) mouse causes an increase in baseline LLF glutathione content which is magnified in an IL-13 model of allergic airway inflammation and protective against asthma. Normal mice are susceptible to asthma in this model but can be protected with acivicin, a GGT inhibitor. GGT is a target to treat asthma but acivicin toxicity limits clinical use. GGsTop is a novel GGT inhibitor. GGsTop inhibits LLF GGT activity only when delivered through the airway. In the IL-13 model, mice treated with IL-13 and GGsTop exhibit a lung inflammatory response similar to that of mice treated with IL-13 alone.
3.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.
Ida T1, Suzuki H2, Fukuyama K1, Hiratake J3, Wada K4. Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):607-14. doi: 10.1107/S1399004713031222. Epub 2014 Jan 31.
γ-Glutamyltranspeptidase (GGT) is an enzyme that plays a central role in glutathione metabolism, and acivicin is a classical inhibitor of GGT. Here, the structure of acivicin bound to Bacillus subtilis GGT determined by X-ray crystallography to 1.8 Å resolution is presented, in which it binds to the active site in a similar manner to that in Helicobacter pylori GGT, but in a different binding mode to that in Escherichia coli GGT. In B. subtilis GGT, acivicin is bound covalently through its C3 atom with sp2 hybridization to Thr403 Oγ, the catalytic nucleophile of the enzyme. The results show that acivicin-binding sites are common, but the binding manners and orientations of its five-membered dihydroisoxazole ring are diverse in the binding pockets of GGTs.
4.Monitoring γ-glutamyl transpeptidase activity and evaluating its inhibitors by a water-soluble near-infrared fluorescent probe.
Li L1, Shi W2, Wu X1, Gong Q1, Li X1, Ma H1. Biosens Bioelectron. 2016 Jul 15;81:395-400. doi: 10.1016/j.bios.2016.03.021. Epub 2016 Mar 12.
The first near-infrared fluorescent probe with excellent water-solubility for γ-glutamyl transpeptidase (GGT) has been developed by combining glutathione (GSH) as a recognition unit with a near-infrared hemicyanine fluorophore through an acrylyl linker. The probe exhibits a highly selective and sensitive fluorescent off-on response to GGT with a detection limit of 0.50U/L, and the response mechanism is based on the enzyme-catalyzed cleavage of the γ-glutamyl bond of GSH, followed by the spontaneous intramolecular cyclization and the release of the fluorophore. Notably, the probe has been used to image GGT in zebrafish and evaluate the inhibition ability of three common inhibitors of GGT both in vitro and in vivo, revealing that their inhibition efficiencies are acivicin >6-diazo-5-oxo-L-norleucine >L-serine-borate complex, and their corresponding IC50 values are 0.11±0.01mM, 0.34±0.04mM and 2.06±0.24mM, respectively. The proposed probe is simple, and may have great potential for screening GGT inhibitors.