59221-35-1

Usage

InChI:InChI=1/C14H19NO5/c16-12(13(17)18)8-4-5-9-15-14(19)20-10-11-6-2-1-3-7-11/h1-3,6-7,12,16H,4-5,8-10H2,(H,15,19)(H,17,18)/t12-/m0/s1

Upstream product

• 102390-88-5 6-benzyloxycarbonylamino-2-oxo-hexanoic acid 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 42491-84-9 (S)-6-Amino-2-hydroxyhexanoic acid 
• 501-53-1 benzyl chloroformate 
• 657-27-2 L-Lysine hydrochloride 

Downstream Products

• 126110-92-7 (2S,3aS,7aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-indole-2-carboxylic acid ethyl ester 
• 126110-93-8 (2S,3aS,6aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 126110-91-6 <1(R^*),2α,4α>-4-cyclohexyl-1-<2-hydroxy-1-oxo-6-<<(phenylmethoxy)carbonyl>amino>hexyl>-L-proline phenylmethyl ester 
• 126110-91-6 (2S,4S)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-4-cyclohexyl-pyrrolidine-2-carboxylic acid benzyl ester 
• 126187-84-6 {4-[(S)-2,5-Dioxo-2-(4-phenyl-butyl)-2λ⁵-[1,3,2]dioxaphospholan-4-yl]-butyl}-carbamic acid benzyl ester 
• 126111-16-8 (S)-6-Benzyloxycarbonylamino-2-(2,2-dimethyl-propionyloxy)-hexanoic acid 
• 126111-17-9 (S)-2-(acetyloxy)-6-<<(phenylmethoxy)carbonyl>amino>hexanoic acid 
• 110931-32-3 1-<(S)-2-hydroxy-1-oxo-6-<<(phenylmethoxy)carbonyl>amino>hexyl>-L-proline phenylmethyl ester 
• 64803-24-3 [(S)-6-(2,5-Dioxo-pyrrolidin-1-yl)-5-hydroxy-6-oxo-hexyl]-carbamic acid benzyl ester 
• 250383-35-8 6-benzyloxycarbonylamino-(2S)-hydroxyhexanoic acid benzyl ester 
• 107492-32-0 (S)-2-hydroxy-6<<(phenylmethoxy)carbonyl>amino>hexanoic acid methyl ester 
• 959919-04-1 (S)-6-amino-2-benzyloxy-N-benzyloxycarbonylhexanoic acid 
• 126187-65-3 (2S,4R)-1-{(S)-6-Amino-2-[hydroxy-(4-phenyl-butyl)-phosphinoyloxy]-hexanoyl}-4-cyclohexyl-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Biodegradable polyester, poly[α-(4-Aminobutyl)-L-glycolic acid], as a non-toxic gene carrier

Purpose. The aim of this study was to develop a non-toxic polymeric gene carrier. For this purpose, biodegradable cationic polymer, poly[α-(4-aminobutyl)-L-glycolic acid] (PAGA) was synthesized. PAGA was designed to have ester linkage because polyesters usually show biodegradability. Methods. Degradation of PAGA in an aqueous solution was followed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). PAGA/DNA complexes were characterized by gel electrophoresis, atomic force microscopy (AFM), dynamic light scattering (DLS). The transfection was measured by using the β-galactosidase reporter gene. Results. PAGA was degraded in aqueous solution very quickly and the final degradation product was a monomer (L-oxylysine). Formation of self-assembling biodegradable complexes between PAGA and DNA at a charge ratio 1:1 (+/-) was confirmed by gel band shift assay and AFM. In these studies, controlled release of DNA from the complexes could be seen. The complexes showed about 2-fold higher transfection efficiency than DNA complexes of poly-L-lysine (PLL), a structural analogue of PAGA, which is the most commonly used poly-cation for gene delivery. The polymer did not show cytotoxicity, possibly because of its degradability and the biocompatibility of the monomer. Conclusions. The use of the biodegradable poly-cation, PAGA, as a DNA condensing agent will be useful in safe gene delivery.

Pluronic-poly[α-(4-aminobutyl)-l-glycolic acid] polymeric micelle-like nanoparticles as carrier for drug delivery

Pluronic-poly[α-(4-aminobutyl)-l-glycolic acid] (Pluronic-PAGA) with different types of Pluronic, the different molecule weight of PAGA, and the different molar ratios of Pluronic to PAGA were synthesized. These materials were bio-degradable, amphiphilic, could be degraded into non-toxic small molecules and could be used to carry drugs. 5-Fluorouracil (5-Fu) loaded Pluronic-PAGA micellelike nanoparticles (5-Fu loaded P-PAGA NPs) were prepared by a simple self-assembly method, and characterized by dynamic light scattering, transmission electron microscope. The degradation and release characteristics have also been studied in this paper. With the time passing, the 5-Fu loaded P-PAGA NPs degraded into smaller ones with the similar characteristics of the original NPs. Both the types of Pluronic and the molecule weight of the PAGA affected the releasing progresses. It was found that 5-Fu loaded P-PAGA NPs exhibited high growth inhibitory effect on human gastric cancer cells by MTT assay. The cellular uptake of Rhodamine B loaded P-PAGA NPs was higher than free Rhodamine B. This study suggested that the Pluronic-PAGA with acceptable drug entrapment efficiencies, drug loading efficiencies and tunable release profiles could offer an alternative carrier for 5-Fu delivery and have the potential for the delivery of other anti-tumour drug. Copyright

Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein

Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.

Conformational studies on peptides of α-aminoxy acids with functionalized side-chains

Peptides of homochiral α- aminoxy acids of nonpolar side chains can form a 1.88-helix. In this paper, we report the conformational studies of α- aminoxy peptides 1-3, which have functionalized side chains, in both non- polar and polar solvents.

POLYBIOTIN COMPOUNDS FOR MAGNETIC RESONANCE IMAGINING AND DRUG DELIVERY

The invention relates generally to biotin-containing compounds that are useful as imaging agents and drug-delivery agents. Another aspect of the invention relates to the aforementioned compounds chelated to a metal atom. In a preferred embodiment, the metal atom is a gadolinium. Another aspect of the invention relates to a compound comprising three biotin moieties and a pharmaceutical agent covalently bound to a heterocyclic core. In certain embodiments, the pharmaceutical agent is an antibiotic, antiviral, or radionuclide. Another aspect of the present invention relates to a method of treating disease involving administering the compounds of the invention to a mammal. Another aspect of the present invention relates to a method of acquiring a magnetic resonance image using the compounds of the invention.

Biocatalytic synthesis of some chiral drug intermediates by oxidoreductases

Chiral intermediates were prepared by biocatalytic processes with oxidoreductases for the chemical synthesis of some pharmaceutical drug candidates. These include: (i) the microbial reduction of 1-(4-fluorophenyl)-4-[4-(5-fluoro-2-pyrimidinyl)-1 -piperazi

ORALLY ACTIVE PHOSPHONYL HYDROXYACYL PROLINES

This invention is directed to orally active antihypertensive agents of the formula STR1 wherein R 1 is certain alkyl or aralkyl groups.