Tag: M.W=250-300

Chen, Qi-Yin; Chaturvedi, Pravin R.; Luesch, Hendrik published the artcile< Process development and scale-up total synthesis of largazole, a potent class I histone deacetylase inhibitor>, COA of Formula: C12H18N2O4S, the main research area is macrocyclic depsipeptide natural product largazole total enantioselective synthesis; largazole anticancer agent histone deacetylase inhibitor drug design; hydrolysis fragment condensation Seebach procedure formylation methylation safety; Aldol condensation enzymic resolution peptide coupling macrocyclization cross metathesis.

Herein we describe the research and development of the process for the scale-up total synthesis of largazole, a potent class I selective histone deacetylase (HDAC) inhibitor, a potential anticancer agent and also useful for the treatment of other disorders where transcriptional reprogramming might be beneficial. The synthetic route and conditions for each fragment and final product were modified and optimized to make them suitable for larger-scale synthesis. With the process we developed, hundreds of grams of each fragment and decagrams of final product largazole were synthesized in good to excellent yields. The final target largazole was obtained in 21% overall yield over eight steps based on the longest sequence with over 95% HPLC purity.

Organic Process Research & Development published new progress about Aldol condensation. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, COA of Formula: C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Lin, Xuexiang; Liu, Xiao-Yu; Zhang, Bo; Qin, Ai-Qing; Hui, Kwok-Min; Shi, Kevin; Liu, Yang; Gabriel, Don; Li, X. James published the artcile< A rapid influenza diagnostic test based on detection of viral neuraminidase activity>, Electric Literature of 2591-17-5, the main research area is neuraminidase enzyme assay influenza diagnosis.

Current methods used for diagnosis of acute infection of pathogens rely on detection of nucleic acids, antigens, or certain classes of antibodies such as IgM. Here we report a virus enzyme assay as an alternative to these methods for detection of acute viral infection. In this method, we used a luciferin derivative as the substrate for detection of the enzyme activity of influenza viral neuraminidase as a means for diagnosis of influenza. The resulting com. test, the qFLU Dx Test, uses a different supply chain that does not compete with those for the current tests. The assay reagents were formulated as a master mix that accommodated both the neuraminidase and luciferase reactions, thereby enabling rapid and prolonged production of stable light signal in the presence of influenza virus in the sample. The assay was evaluated using depository throat swab specimens. As expected, the assay exhibited similar detection rates for all influenza types and subtypes except for A(H7N9), which exhibited lower detection rate due to lower viral titer in the specimens. When throat swab specimens were diluted with the sample buffer of the test kit and tested with the qFLU Dx Test. The sensitivity and specificity were 82.41% (95% confidence interval: 79.66-85.84%) and 95.39% (95% confidence interval: 94.32-96.46%), resp., for these diluted specimens in comparison to a real-time polymerase chain reaction assay. The uniqueness of the qFLU Dx Test as an enzymic assay makes it highly complementary with currently available methods.

Scientific Reports published new progress about Diagnosis. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Electric Literature of 2591-17-5.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Ikeda, Yuma; Nomoto, Takahiro; Hiruta, Yuki; Nishiyama, Nobuhiro; Citterio, Daniel published the artcile< Ring-Fused Firefly Luciferins: Expanded Palette of Near-Infrared Emitting Bioluminescent Substrates>, Computed Properties of 2591-17-5, the main research area is ring fused firefly luciferin near IR emitting bioluminescence substrate.

Firefly bioluminescence is broadly applied as a noninvasive imaging modality in the biomedical research field. One limitation in firefly bioluminescence imaging is the limited variety of luciferins emitting in the near-IR (NIR) region (650-900 nm), where tissue penetration is high. Herein, we describe a series of structure-inherent NIR emitting firefly luciferin analogs, NIRLucs, designed through a ring fusion strategy. This strategy resulted in pH-independent structure-inherent NIR emission with a native firefly luciferase, which was theor. supported by quantum chem. calculations of the oxidized form of each luciferin. When applied to cells, NIRLucs displayed dose-independent improved NIR emission even at low concentrations where the native D-luciferin substrate does not emit. Addnl., excellent blood retention and brighter photon flux (7-fold overall, 16-fold in the NIR spectral range) than in the case of D-luciferin have been observed with one of the NIRLucs in mice bearing s.c. tumors. We believe that these synthetic luciferins provide a solution to the longstanding limitation in the variety of NIR emitting luciferins and pave the way to the further development of NIR bioluminescence imaging platforms.

Analytical Chemistry (Washington, DC, United States) published new progress about Bioluminescence. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Computed Properties of 2591-17-5.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Yu, Xiaoling; Zhang, Bingbing; Shan, Guangsheng; Wu, Yue; Yang, Feng-Ling; Lei, Xinsheng published the artcile< Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A>, Product Details of C12H18N2O4S, the main research area is macrocyclic depsipeptide hybrid thiol synthesis HDAC inhibitor antitumor agent; natural product largazole psammaplin A drug design; methylcysteine acylation cyclocondensation thiazole thiazoline hydrolysis; malic acid cyclocondensation trichloro ethanediol esterification amidation; macrolactamization protective group.

One important class of HDAC (histone deacetylation enzymes) inhibitors is the sulfur-containing marine natural products with structural diversity. Inspired by two structurally distinguishing examples, Largazole and Psammaplin A, which possess macrocyclic depsipeptide and simple linear amide scaffold resp., we designed one novel mol. hybrid by replacing the alkene moiety in Largazole with a semirigid amide bond. This hybrid compound has been synthesized from L-malic acid in 10 steps with an overall yield of 7%. The preliminary biol. assays suggest that the replacement of trans olefin moiety with amide bond will lead to an unbeneficial effect on the inhibition against HDACs.

Tetrahedron published new progress about (Fluorenylmethoxy)carbonyl group. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Product Details of C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Pena, Stella; Scarone, Laura; Manta, Eduardo; Serra, Gloria published the artcile< First total synthesis of aerucyclamide B>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is cyclic peptide aerucyclamide B total synthesis antimalarial agent fluorous; oxathiozole hydroxyamide cyclodehydration Deoxo Fluor peptide coupling fragment condensation; natural product Microcystis aeruginosa cyanobacteria.

The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-l-allo-Thr-l-Ile-Thz-d-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the β-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%).

Tetrahedron Letters published new progress about Antimalarials. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Stress, Cedric J.; Sauter, Basilius; Schneider, Lukas A.; Sharpe, Timothy; Gillingham, Dennis published the artcile< A DNA-Encoded Chemical Library Incorporating Elements of Natural Macrocycles>, Quality Control of 96929-05-4, the main research area is DNA encoded library macrocycle compound; DNA chemistry; DNA-encoded libraries; Lipinski rules; chemical libraries; macrocycles.

Here the authors show a seven-step chem. synthesis of a DNA-encoded macrocycle library (DEML) on DNA. Inspired by polyketide and mixed peptide-polyketide natural products, the library was designed to incorporate rich backbone diversity. Achieving this diversity, however, comes at the cost of the custom synthesis of bifunctional building block libraries. This study outlines the importance of careful retrosynthetic design in DNA-encoded libraries, while revealing areas where new DNA synthetic methods are needed.

Angewandte Chemie, International Edition published new progress about Combinatorial library (DNA-encoded). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Quality Control of 96929-05-4.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Yu, Mohan; Liu, Yajun published the artcile< A QM/MM Study on the Initiation Reaction of Firefly Bioluminescence-Enzymatic Oxidation of Luciferin>, Application In Synthesis of 2591-17-5, the main research area is luciferin bioluminescence enzymic oxidation quantum mol mechanic study; QM/MM; firefly bioluminescence; luciferin oxidation; mechanism; single electron transfer.

Among all bioluminescent organisms, the firefly is the most famous, with a high luminescent efficiency of 41%, which is widely used in the fields of biotechnol., biomedicine and so on. The entire bioluminescence (BL) process involves a series of complicated in-vivo chem. reactions. The BL is initiated by the enzymic oxidation of luciferin (LH2). However, the mechanism of the efficient spin-forbidden oxygenation is far from being totally understood. Via MD simulation and QM/MM calculations, this article describes the complete process of oxygenation in real protein. The oxygenation of luciferin is initiated by a single electron transfer from the trivalent anionic LH2 (L3-) to O2 to form 1[L•2-…O2•-]; the entire reaction is carried out along the ground-state potential energy surface to produce the dioxetanone (FDO-) via three transition states and two intermediates. The low energy barriers of the oxygenation reaction and biradical annihilation involved in the reaction explain this spin-forbidden reaction with high efficiency. This study is helpful for understanding the BL initiation of fireflies and the other oxygen-dependent bioluminescent organisms.

Molecules published new progress about Annihilation radiation. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Application In Synthesis of 2591-17-5.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Zhang, Ru; He, Jinwu; Dong, Zhiwei; Liu, Guichun; Yin, Yuan; Zhang, Xinying; Li, Qi; Ren, Yandong; Yang, Yongzhi; Liu, Wei; Chen, Xianqing; Xia, Wenhao; Duan, Kang; Hao, Fei; Lin, Zeshan; Yang, Jie; Chang, Zhou; Zhao, Ruoping; Wan, Wenting; Lu, Sihan; Peng, Yanqiong; Ge, Siqin; Wang, Wen; Li, Xueyan published the artcile< Genomic and experimental data provide new insights into luciferin biosynthesis and bioluminescence evolution in fireflies>, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid, the main research area is Lamprigera luciferin bioluminescence evolution.

Abstract: Fireflies are among the most charismatic insects for their spectacular bioluminescence, but the origin and evolution of bioluminescence remain elusive. Especially, the genic basis of luciferin (D-luciferin) biosynthesis and light patterns is largely unknown. Here, we present the high-quality reference genomes of two fireflies Lamprigera yunnana (1053 Mb) and Abscondita terminalis (501 Mb) with great differences in both morphol. and luminous behavior. We sequenced the transcriptomes and proteomes of luminous organs of two species. We created the CRISPR/Cas9-induced mutants of Abdominal B gene without luminous organs in the larvae of A. terminalis and sequenced the transcriptomes of mutants and wild-types. Combining gene expression analyses with comparative genomics, we propose a more complete luciferin synthesis pathway, and confirm the convergent evolution of bioluminescence in insects. Using experiments, the function of the firefly acyl-CoA thioesterase (ACOT1) to convert L-luciferin to D-luciferin was validated for the first time. Comparisons of three-dimension reconstruction of luminous organs and their differentially expressed genes among two species suggest that two pos. genes in the calcium signaling pathway and structural difference of luminous organs may play an important role in the evolution of flash pattern. Altogether, our results provide important resources for further exploring bioluminescence in insects.

Scientific Reports published new progress about Aquatica lateralis. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Cheng, Gang; Pan, Jing; Podsiadly, Radoslaw; Zielonka, Jacek; Garces, Alexander M.; Dias Duarte Machado, Luiz Gabriel; Bennett, Brian; McAllister, Donna; Dwinell, Michael B.; You, Ming; Kalyanaraman, Balaraman published the artcile< Increased formation of reactive oxygen species during tumor growth: Ex vivo low-temperature EPR and in vivo bioluminescence analyses>, Computed Properties of 2591-17-5, the main research area is ROS tumor growth bioluminescence analysis boronate proluciferin probe ESR; Bioluminescence; EPR; Mitochondria; Oxidants; Tumor growth.

Previous studies have shown that reactive oxygen species (ROS) such as superoxide or hydrogen peroxide generated at low levels can exert a tumor-promoting role via a redox-signaling mechanism. Reports also suggest that both tumorigenesis and tumor growth are associated with enhanced ROS formation. However, whether ROS levels or ROS-derived oxidative marker levels increase during tumor growth remains unknown. In this study, in vivo bioluminescence imaging with a boronate-based pro-luciferin probe was used to assess ROS formation. Addnl., probe-free cryogenic ESR was used to quantify a characteristic aconitase [3Fe4S]+ center that arises in the tumor tissue of mouse xenografts from the reaction of the native [4Fe4S]2+ cluster with superoxide. Results indicated that tumor growth is accompanied by increased ROS formation, and revealed differences in oxidant formation in the inner and outer sections of tumor tissue, resp., demonstrating redox heterogeneity. Studies using luciferin and pro-luciferin probes enabled the assessment of tumor size, ROS formation, and bioenergetic status (e.g., ATP) in luciferase-transfected mice tumor xenografts. Probe-free ex vivo low-temperature ESR can also be translated to clin. studies.

Free Radical Biology & Medicine published new progress about Animal cell line (H2030). 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Computed Properties of 2591-17-5.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Tohidnezhad, Mersedeh; Kubo, Yusuke; Lichte, Philipp; Heigl, Tobias; Roch, Diana; Pour, Nazanin Barahmand; Bergmann, Christian; Soenmez, Tolga Taha; Hock, Jennifer Vanessa Phi; Fragoulis, Athanassios; Gremse, Felix; Rosenhain, Stefanie; Slowik, Alexander; Bienert, Michaela; Kweider, Nisreen; Wruck, Christoph Jan; Jahr, Holger; Hildebrand, Frank; Pape, Hans Christoph; Neu, Sabine; Fischer, Horst; Pufe, Thomas published the artcile< Effects of strontium-doped β-tricalcium scaffold on longitudinal nuclear factor-kappa beta and vascular endothelial growth factor receptor-2 promoter activities during healing in a murine critical-size bone defect model>, Formula: C11H8N2O3S2, the main research area is strontium doped tricalcium scaffold nuclear factor kappa beta; vascular endothelial growth factor receptor healing murine bone defect; NF-κB; VEGFR-2; bioluminescence; large bone defects; strontium; β-tricalcium phosphate.

It was hypothesized that strontium (Sr)-doped β-tricalcium phosphate (TCP)-based scaffolds have a pos. effect on the regeneration of large bone defects (LBD). Readouts in our mice models were nuclear factor-kappa beta (NF-κB) activity and vascular endothelial growth factor receptor-2 (VEGFR-2) promoter activity during the healing process. A 2-mm critical-size femoral fracture was performed in transgenic NF-κB- and VEGFR-2-luciferase reporter mice. The fracture was filled with a 3D-printed β-TCP scaffold with or without Sr. A bioluminescence in-vivo imaging system was used to sequentially investigate NF-κB and VEGFR-2 expression for two months. After sacrifice, soft and osseous tissue formation in the fracture sites was histol. examined NF-κB activity increased in the β-TCP + Sr group in the latter stage (day 40-60). VEGFR-2 activity increased in the + Sr group from days 0-15 but decreased and showed significantly less activity than the β-TCP and non-scaffold groups from days 40-60. The new bone formation and soft tissue formation in the + Sr group were significantly higher than in the β-TCP group, whereas the percentage of osseous tissue formation in the β-TCP group was significantly higher than in the β-TCP + Sr group. We analyzed longitudinal VEGFR-2 promoter activity and NF-κB activity profiles, as resp. agents of angiogenesis and inflammation, during LBD healing. The extended inflammation phase and eventually more rapid resorption of scaffold caused by the addition of strontium accelerates temporary bridging of the fracture gaps. This finding has the potential to inform an improved treatment strategy for patients who suffer from osteoporosis.

International Journal of Molecular Sciences published new progress about Angiogenesis. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Formula: C11H8N2O3S2.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica