13095-73-3

Usage

Uses

Used in Chemical Synthesis:
4-Mercaptobutyric Acid is used as a synthetic intermediate for the production of a wide range of organic compounds. Its reactivity and functional groups make it a useful building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Acyclic Compounds:
4-Mercaptobutyric Acid is used as a precursor in the synthesis of acyclic compounds, which are characterized by their open chain structure. These compounds have various applications in different industries, including the production of solvents, detergents, and other industrial chemicals.
Used in Alkanes:
4-Mercaptobutyric Acid can be used in the synthesis of alkanes, which are saturated hydrocarbons with single bonds between carbon atoms. Alkanes are widely used as fuels, solvents, and raw materials for the production of various chemical products.
Used in Building Blocks:
As an organic building block, 4-Mercaptobutyric Acid is employed in the construction of more complex organic molecules. Its presence in these molecules can impart unique properties, such as increased reactivity or the ability to form stable complexes with metal ions.
Used in the Production of Thiols:
4-Mercaptobutyric Acid can be used as a starting material for the synthesis of other thiols, which are important in various applications, including the production of rubber, pharmaceuticals, and agrochemicals. Thiols are known for their strong, characteristic odor and their ability to react with a wide range of compounds.

InChI:InChI=1/C4H8O2S/c5-4(6)2-1-3-7/h7H,1-3H2,(H,5,6)

Upstream product

• 96-48-0 4-butanolide 
• 17356-08-0 thiourea 
• 70124-54-8 ethyl 4-mercaptobutanoate 
• 101421-82-3 S-acetyl-4-mercaptobutyric acid 
• 2906-60-7 5,6-dithia-decanedioic acid 
• 1003-10-7 Thiobutyrolactone 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 2623-87-2 bromobutyric acid 
• 2969-81-5 Ethyl 4-bromobutyrate 

Downstream Products

• 1003-10-7 Thiobutyrolactone 
• 2906-60-7 5,6-dithia-decanedioic acid 
• 29982-03-4 2-(γ-Mercaptopropyl)-benzimidazol 
• 250266-79-6 4-(pyridin-2-yldisulfanyl)butanoic acid 
• 377733-71-6 4-[(triphenylmethyl)thio]butanoic acid 
• 107-92-6 butyric acid 
• 1160162-67-3 (RS)-2-amino-4-[(3-carboxypropyl)disulfanyl]butanoic acid 
• 32391-97-2 4-(methylthio)butanoic acid 

Relevant academic research and scientific papers

A self-assembled, ROS-responsive Janus-prodrug for targeted therapy of inflammatory bowel disease

A self-assembled and oxidation-degradable Janus-prodrug, termed as Bud-ATK-Tem (B-ATK-T), was fabricated by ROS-responsive aromatized thioketal (ATK) linked anti-inflammatory drug budesonide (Bud) and antioxidant tempol (Tem). Benefiting from the hydrophobic interactions and π-π stacking interactions of ATK, prodrug B-ATK-T could self-assemble into nanoparticles (NP) in water containing lecithin and DSPE-PEG2K. The morphology of B-ATK-T NP (approximate 100–120 nm) was confirmed to be regular spherical by transmission electron microscope. B-ATK-T NP was endowed high drug loading content with 41.23% for Bud and 15.55% for Tem. The rapid drug release from B-ATK-T NP proceeded in an extensive reactive oxygen species (ROS)-dependent manner. More than 98% of Bud and Tem in B-ATK-T NP could release in the mimic inflammation microenvironment or phorbol-12-myristate-13-acetate (PMA)-stimulated macrophages within short time. The release of drugs in a simultaneous and proportional manner ensures that B-ATK-T NP can increase the combined efficacy of anti-inflammation and anti-oxidation. It is worth noting that B-ATK-T NP could be passively accumulated and dramatically increasing the maximum drugs concentration in the inflamed colon of mice with inflammatory bowel disease (IBD) by oral route, and avoiding potential systemic side effects. B-ATK-T NP could not only relieve colitis via inhibiting the expression of oxidative and proinflammatory mediators more than combination of free drugs, but also significantly reduce colitis-caused death. Taken together, the self-assembled, Janus-prodrug B-ATK-T NP is a promising candidate therapies for IBD, even for other inflammatory diseases.

FILAMENTOUS NANOSTRUCTURES AND THEIR USE FOR TREATMENT OF PULMONARY DISEASE

The present invention provides supramolecular filament and/or sphere compositions and their use as inhalable drug carriers within aerosols. The invention provides insights into peptide designs and supramolecular stability and its crucial role in the interfacial stability and aerosolization properties of the supramolecular filament and/or sphere compositions. The compositions and their properties show that molecular enrichment at the air-liquid interface during nebulization is the primary factor to deplete the monomeric peptide amphiphiles in solution, accounting for the observed morphological disruption/transitions. Importantly, encapsulation of drugs and dyes within the inventive filament and/or sphere compositions notably stabilize their supramolecular structure during nebulization, and the loaded filaments exhibit a linear release profile from a nebulizer device. The compositions disclosed herein can be used as an effective platform for the inhalation-based treatment of many lung and sinusoidal diseases.

Her2 targeted polypeptide drug conjugate as well as a preparation method and application thereof

The invention relates to an Her2 targeted polypeptide drug conjugate as well as a preparation method and application thereof. The Her2 targeted polypeptide drug conjugate has a molecular structural formula shown in a formula I, wherein Aaa1 is L or D type Lys or Arg; Aaa2 is L or D type Lys or Arg; X is CH2, NH or O; ROH is a hydrophobic antitumor drug; and n is 1 or 2. The Her2 targeted polypeptide drug conjugate provided by the invention can realize targeted drug delivery, the targeted polypeptide can transport the antitumor drug to specific tumor cells, the drug enters the tumor cells and then exerts the characteristic of specific degradation of disulfide bonds at tumor sites, and the antitumor drug is rapidly released. Compared with conventional joint arms such as 2,2'-dithiodiglycolicacid and 3,3'-dithiodipropionic acid, the Her2 targeted polypeptide drug conjugate provided by the invention has the advantages that an anticancer drug in the form of an original drug molecule can beobtained without further hydrolysis, the drug efficacy is improved, and the toxic and side effects on normal cells are reduced.

Supramolecular Design of Unsymmetric Reverse Bolaamphiphiles for Cell-Sensitive Hydrogel Degradation and Drug Release

Self-assembly of peptide-based building units into supramolecular nanostructures creates an important class of biomaterials with robust mechanical properties and improved resistance to premature degradation. Yet, upon aggregation, substrate–enzyme interactions are often compromised because of the limited access of macromolecular proteins to the peptide substrate, leading to either a reduction or loss of responsiveness to biomolecular cues. Reported here is the supramolecular design of unsymmetric reverse bolaamphiphiles (RBA) capable of exposing a matrix metalloproteinase (MMP) substrate on the surface of their filamentous assemblies. Upon addition of MMP-2, these filaments rapidly break into fragments prior to reassembling into spherical micelles. Using 3D cell culture, it is shown that drug release is commensurate with cell density, revealing more effective cell killing when more cancer cells are present. This design platform could serve as a cell-responsive therapeutic depot for local chemotherapy.

Based on molecular glue of the fluorescence-labeled nucleotide and its use in DNA sequencing

The invention discloses a fluorescence labelled nucleotide based on a molecular glue and a use thereof in DNA sequencing. The structure formula of the fluorescence labelled nucleotide is shown in a formula (I) in the specification, wherein R1 is shown in the specification, R2 is fluorescein or shown in the specification, and dNTP is ribonucleoside triphosphote which contains four different base groups; the fluorescein is selected from one of the BODIPY, rhodamine, coumarin, xanthene, cyanin, pyrene, phthalocyanine, alexa, a squarene dye, a composition for generating energy transfer dye and the derivatives thereof. The fluorescence labelled nucleotide can be used for DNA sequencing; simultaneously the raw materials for synthesizing the fluorescence labelled nucleotide are simple and easy to obtain and the fluorescence labelled nucleotide can be used for large-scale popularization. The biological assessment result shows that all the requirements of the high-throughput sequencing biochemical reaction can be satisfied by the reversible terminal, and the reversible terminal has good practical prospect.

Structure-activity relationships of small molecule autotaxin inhibitors with a discrete binding mode

Autotaxin (ATX) is a secreted enzyme responsible for the hydrolysis of lysophosphatidylcholine (LPC) to the bioactive lysophosphatidic acid (LPA) and choline. The ATX-LPA signaling pathway is implicated in cell survival, migration, and proliferation; thus, the inhibition of ATX is a recognized therapeutic target for a number of diseases including fibrotic diseases, cancer, and inflammation, among others. Many of the developed synthetic inhibitors for ATX have resembled the lipid chemotype of the native ligand; however, a small number of inhibitors have been described that deviate from this common scaffold. Herein, we report the structure-activity relationships (SAR) of a previously reported small molecule ATX inhibitor. We show through enzyme kinetics studies that analogues of this chemotype are noncompetitive inhibitors, and by using a crystal structure with ATX we confirm the discrete binding mode.

Molecular design and synthesis of self-assembling camptothecin drug amphiphiles

The conjugation of small molecular hydrophobic anticancer drugs onto a short peptide with overall hydrophilicity to create self-assembling drug amphiphiles offers a new prodrug strategy, producing well-defined, discrete nanostructures with a high and quantitative drug loading. Here we show the detailed synthesis procedure and how the molecular structure can influence the synthesis of the self-assembling prodrugs and the physicochemical properties of their assemblies. A series of camptothecin-based drug amphiphiles were synthesized via combined solid- and solution-phase synthetic techniques, and the physicochemical properties of their self-assembled nanostructures were probed using a number of imaging and spectroscopic techniques. We found that the number of incorporated drug molecules strongly influences the rate at which the drug amphiphiles are formed, exerting a steric hindrance toward any additional drugs to be conjugated and necessitating extended reaction time. The choice of peptide sequence was found to affect the solubility of the conjugates and, by extension, the critical aggregation concentration and contour length of the filamentous nanostructures formed. In the design of self-assembling drug amphiphiles, the number of conjugated drug molecules and the choice of peptide sequence have significant effects on the nanostructures formed. These observations may allow the fine-tuning of the physicochemical properties for specific drug delivery applications, ie systemic vs local delivery.

Redox-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-lactic acid) for intracellular drug delivery

Redox-responsive micelles self-assembled from triblock copolymers of poly(l-lactic acid)-poly(ethylene glycol)-poly(l-lactic acid) (PLA-PEG-PLA) with double-disulfide linkage in the backbone were synthesized and characterized by proton nuclear magnetic resonance (1H NMR) and size exclusion chromatography (SEC), in which both PEG (Mn = 1000, 2000 and 4000 g mol-1) and PLA (Mn = 1600 g mol-1) have different molecular weights respectively. The triblock copolymers PLA3000-PEG2000-PLA3000 and PLA3000-PEG4000-PLA3000 can self-assemble into flower-like micelles in aqueous media with average diameters 110 nm and 43 nm and lower critical micelle concentrations (CMC) 0.017 and 0.014 mg mL-1 respectively compared with that of diblock copolymers. Moreover, in vitro drug release analyses indicated that reductive environment can result in triggered drug release profiles. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl- 2-H-tetrazolium bromide (MTT) assay in vitro showed no significant cytotoxicity as NIH 3T3 cells incubated in the micelles even when the concentrations up to 1000 μg/mL. Additionally fluorescence microscopy measurements and MTT assay demonstrated that the micelles exhibited a faster drug release and higher cellular proliferation inhibition due to the effect of intracellular reduction responsiveness compared with that of diblock copolymers. The above results suggest that the reduction-responsive, biodegradable and biocompatibility micelles could provide a platform to construct potential drug delivery systems for cancer therapy.

Dynamic covalent diblock copolymers: Instructed coupling, micellation and redox responsiveness

Instructed by association units that allow reversible and unsymmetrical disulfide bond formation, hydrophilic (PEG) and hydrophobic (PLA) polymer chains are efficiently coupled into amphiphilic diblock copolymers. The desymmetrization of otherwise symmetrical reversible disulfide bond formation is achieved with amide association units that integrate both directional H-bonding and reversible disulfide bond formation, which ensure the connection of different polymer blocks while minimizing self-coupling. The resultant amphiphilic block copolymers self-assemble into long-lasting spherical micelles that are responsive to free thiols.

NOVEL SELF-ASSEMBLING DRUG AMPHIPHILES AND METHODS FOR SYNTHESIS AND USE

The present invention provides herein the design of monodisperse, amphiphilic anticancer drugs—which are now termed “drug amphiphiles” (DAs)—that can spontaneously associate into discrete, stable supramolecular nanostructures with the potential for self-delivery (no additional carriers are needed). The quantitative drug loading in the resulting nanostructures is ensured by the very nature of the molecular design. The DA is a composition comprising: D-L-PEP; wherein D is 1 to 4 hydrophobic drug molecules which can be the same or different; L is 1 to 4 biodegradable linkers which can be the same or different; and PEP is a peptide that can spontaneously associate into discrete, stable supramolecular nanostructures. In an alternate embodiment, the DA composition also comprises a targeting ligand (T). Methods of making DA molecules, as well as their use in treatment of disease are also provided.