90-65-3 Usage
Description
Penicillic acid is a mycotoxin produced from Penicillium species identified in molds on corn and other grains. It is a white to light beige crystalline compound or powder that has the ability to inhibit bacterial quorum sensing communication, making it a potential alternative to conventional methods of fighting bacterial infections.
Uses
Used in Medical Applications:
Penicillic acid is used as a quorum sensing inhibitor for disrupting virulence expression in gram-negative bacteria. At 80 μM, it inhibits bacterial quorum sensing communication in P. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes. Additionally, it has been shown to inhibit Fas-mediated apoptosis at 100-200 μM by targeting caspase-8 activity in Burkitt’s lymphoma Raji cells.
Used in Agricultural Applications:
Penicillic acid can be isolated from the seed-borne fungus Aspergillus persii EML-HPB1-11 and exhibits antibacterial activity against various plant pathogenic bacteria. PENICILLIC ACID can be a potential lead molecule for developing synthetic agrochemicals to protect crops from bacterial infections.
Safety Profile
Poison by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
in vitro
the compound was active primarily against gram-negative bacteria, and it was also active against some gram-positive species. it showed limited antihelminthic properties but did affect the growth of oat seed coleoptiles by interference with the respiratory process. penicillic acid has proven to be too toxic for use in therapy [1]. penicillic acid (80 μm) inhibited bacterial quorum sensing communication in p. aeruginosa by selectively repressing various virulence factor and other quorum sensing-regulated genes [2]. in burkitt’s lymphoma raji cells, penicillic acid exihibited an inhibitory effect on fas-mediated apoptosis at 100-200 μm by targeting caspase-8 activity [3].
in vivo
the ldso (subcutaneous injection) for mice is 100 mg/kg. subcutaneous injection of 1.0 mg/dose twice weekly produced transplantable tumors after 64 weeks in all rats surviving treatment. in addition, a dose at 0.1 mg initiated tumor development [1].
Purification Methods
The lactone (furanone, anhydrous) hydrolyses to the acid (3-methoxy-4-oxo-hexa-2,5-dienoic acid, hydrate). It crystallises from water as the monohydrate (acid), or from pet ether as the anhydrous (lactone) compound. The free acid is in equilibrium with the lactone. UV: max 221nm ( 12,500) in 0.02M KOH; 228nm ( 11,500) in 0.02M HCl [Raphael J Chem Soc 1508 1948]. [Beilstein 3 II 519, 3 III 1467.] It is a possible antineoplastic.
references
[1] ciegler a, detroy r w, lillehoj e b. patulin, penicillic acid, and other carcinogenic lactones[j]. microbial toxins, 1971, 6: 409-434.[2] rasmussen t b, skindersoe m e, bjarnsholt t, et al. identity and effects of quorum-sensing inhibitors produced by penicillium species[j]. microbiology, 2005, 151(5): 1325-1340.[3] bando m, hasegawa m, tsuboi y, et al. the mycotoxin penicillic acid inhibits fas ligand-induced apoptosis by blocking self-processing of caspase-8 in death-inducing signaling complex[j]. journal of biological chemistry, 2003, 278(8): 5786-5793.
Check Digit Verification of cas no
The CAS Registry Mumber 90-65-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 90-65:
(4*9)+(3*0)+(2*6)+(1*5)=53
53 % 10 = 3
So 90-65-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/p-1