Flashcards: Diketopiperazines

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin.

Rhodotorulic acid is the smallest of the 2,5-diketopiperazine family of hydroxamate siderophores which are high-affinity chelating agents for ferric iron, produced by bacterial and fungal phytopathogens for scavenging iron from the environment.

Epelsiban (INN, USAN, code name GSK-557,296-B) is an orally bioavailable drug which acts as a selective, sub-nanomolar (Ki = 0.13 nM) oxytocin receptor antagonist with >31,000-fold selectivity over the related vasopressin receptors and is being developed by GlaxoSmithKline for the treatment of premature ejaculation in men and as an agent to enhance embryo or blastocyst implantation in women undergoing embryo or blastocyst transfer associated with in vitro fertilization (IVF).

Plinabulin (NPI-2358) is a 2,5-diketopiperazine derivative that is being developed as an experimental cancer drug.

Dideoxyverticillin A (+)-11,11’-dideoxyverticillin A is a complex epipolythiodioxopiperazine initially isolated from the marine fungus Penicillium sp.

2,5-Diketopiperazine, also known as piperazine-2,5-dione and as the cyclodipeptide cyclo(Gly-Gly), is an organic compound and the smallest cyclic dipeptide that consists of a six-membered ring containing two amide linkages where the two nitrogen atoms and the two carbonyls are at opposite positions in the ring.

Roquefortine C is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from the Penicillium genus.

Dexrazoxane hydrochloride (Zinecard by Pfizer in USA and Canada; Cardioxane by Clinigen Group for EU and other countries) is a cardioprotective agent.

Spirotryprostatin B is an indolic alkaloid found in the Aspergillus fumigatus fungus that belongs to a class of naturally occurring 2,5-diketopiperazines.

Spirotryprostatin A is an indolic alkaloid from the 2,5-Diketopiperazine class of natural products found in the Aspergillus fumigatus fungus.

ICRF 193 is a topoisomerase inhibitor.

Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteusn that was isolated from Streptomyces sapporonesis and Streptomyces aizumenses in 1972.

Tadalafil is a PDE5 inhibitor marketed in pill form for treating erectile dysfunction (ED) under the name Cialis, and under the name Adcirca for the treatment of pulmonary arterial hypertension.

Aplaviroc (INN, codenamed AK602 and GSK-873140) is a CCR5 entry inhibitor that belongs to a class of 2,5-diketopiperazines developed for the treatment of HIV infection.

Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class.

Brevianamides are indole alkaloids that belong to a class of naturally occurring 2,5-diketopiperazines produced as secondary metabolites of fungi in the genus Penicillium and Aspergillus.

Retosiban (GSK-221,149-A) is an oral drug which acts as a selective, sub-nanomolar (Ki = 0.65 nM) oxytocin receptor antagonist with >1400-fold selectivity over the related vasopressin receptors and is being developed by GlaxoSmithKline for the treatment of preterm labour.

Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines.

(−)-Aurantiamine is a blue fluorescence metabolite produced by the fungus Penicillium aurantiogriseum, the most common fungi found in cereals.

Phenylahistin is a metabolite produced by the fungus Aspergillus ustus that belongs to a class of naturally occurring 2,5-diketopiperazines featuring a dehydrohistidine residue that exhibit important biological activities, such as anti-cancer or neurotoxic effects.

Brevianamide F , also known as cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines.