Current routes for synthesizing antibody-drug conjugates commonly rely on maleimide linkers to react with cysteine thiols. However, thioether exchange with metabolites and serum proteins can compromise conjugate stability and diminish in vivo efficacy. We report the application of a phenyloxadiazole sulfone linker for the preparation of trastuzumab conjugates. This sulfone linker site-specifica...

An octapeptide from Escherichia coli thioredoxin reductase has been isolated and sequenced; it contains the cystine previously shown to take part in electron transfer. The peptide was isolated from a peptic digest of a derivative in which the free sulfhydryls of the enzyme had been reacted with the colored maleimide, N-(4-dimethylamino-3 ,S-dinitrophenyl)maleimide. The sequence of this peptide ...

Reaction of the novel thiopropyl-closo-1,2-carborane ligand bearing a pendant glycerol group HS(CH(2))(3)CB(10)H(10)CCH(2)OCH(CH(2)OH)(2)(L) with the labile platinum(ii) precursor [Pt(MeCN)(terpy)](OTf)(2)(terpy = 2,2':6',2''-terpyridine; OTf = trifluoromethanesulfonate) affords the highly water-soluble platinum(ii) complex [PtL(terpy)]OTf, the first example of a metal-carborane complex functio...

A novel thiol-reactive bifunctional agent, an analogue of fluorobenzaldehyde-O-[6-(2,5-dioxo-2,5dihydro-pyrrol-1-yl)-hexyl]oxime, (FBAM) has been synthesized. The new prosthetic group, [18F]FBAMPy, replaces the 4-fluorophenyl moiety with a 2-fluoropyridinyl moiety leading to increased polarity (FBAM analytical HPLC Rf = 6.4 min; FBAMPy Rf = 4.8 min) while retaining the sulfurreactive pendant. B...

Excimer-forming cysteines in tubulin are detected by the presence of excimer fluorescence in N-(1-pyrenyl)maleimide-labeled tubulin. The ratio of excimer/monomer fluorescence of labeled protein remained unchanged upon its dilution. These results indicating that both partner of each pair(s) of cysteine are located in the same subunit. The excimer fluorescence is insensitive to prior treatment of...

Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione a...

A new compound maleimide-5-oxime was isolated, together with 3,4-dihydroxybenzoic acid, tetillapyrone, from the ethyl acetate extract of the marine sponge Haliclona baeri while tetillapyrone, nortetillapyrone, p-hydroxybenzaldehyde and phenylacetic acid were isolated from the ethyl acetate extract of Haliclona cymaeformis, collected from the Gulf of Thailand. The structures of tetillapyrone and...

A fluorescent compound 3,4-bis(2,4-difluorophenyl)-maleimide from the 3,4-diaryl-substituted maleimides was synthesized and determined to have a Stokes shift of 140 nm (λ(abs) 341 nm, λ(em) 481 nm), a high fluorescent quantum yield (Φ(fl) 0.61) and an extinction coefficient ε((340)) of 48 400 M(-1) cm(-1) in dichloromethane. For the first time we demonstrated the successful implementation of a...

The intramolecular ruthenium(II)-catalyzed radical addition of the trichloroacetyl pendant group to the 2-oxazolone skeleton is greatly enhanced in the presence of catalytic Lewis acids including rare earth metal triflates, thus providing a convenient route to a highly potential chiral synthon for vic-amino alcohols.

The concept of splayed, hyperthin polyelectrolyte multilayers (PEMs) is introduced in which a bulky, hydrophilic and charged pendant group is used to increase the gas permeability of a PEM without reducing its permeation selectivity. Proof of principle studies are reported using nm-thick PEMs made from poly(sodium 4-styrene sulfonate) () and poly(allylamine hydrochloride) () bearing bulky cobal...