Tag: M.W=250-300

Aihara, Kazuhiro; Kano, Yuko; Shiokawa, Sohjiro; Sasaki, Toshiro; Setsu, Fumihito; Sambongi, Yumiko; Ishii, Miyuki; Tohyama, Kazuyo; Ida, Takashi; Tamura, Atsushi; Atsumi, Kunio; Iwamatsu, Katsuyoshi published the artcile< CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure-Activity Relationships>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is methylcarbapenem antimicrobial activity.

A series of 1β-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogs showed potent antibacterial activities against Gram-pos. bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-neg. bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, i.e., imipenem (IPM), panipenem (PAPM), and meropenem (MEPM).

Bioorganic & Medicinal Chemistry published new progress about Antimicrobial agents. 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

Wahyudi, Hendra; Tantisantisom, Worawan; Liu, Xuechao; Ramsey, Deborah M.; Singh, Erinprit K.; McAlpine, Shelli R. published the artcile< Synthesis, structure-activity analysis, and biological evaluation of sanguinamide B analogues>, Quality Control of 96929-05-4, the main research area is sanguinamide B analog synthesis antibacterial structure activity twitching motility; natural product antibiotic sanguinamide conformation conformer; peptide coupling Hantzsch cyclocondensation macrocyclization.

We report the first synthesis of sanguinamide B analogs. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogs all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogs showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a ‘pseudoequatorial’ position, and all other energy considerations are secondary.

Journal of Organic Chemistry published new progress about Antibacterial agents. 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

Ren, Yiqian; Qiang, Yao; Zhu, Beibei; Tang, Wei; Duan, Xinrui; Li, Zhengping published the artcile< General strategy for bioluminescence sensing of peptidase activity in vivo based on tumor-targeting probiotic>, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid, the main research area is human leucine aminopeptidase bioluminescence sensing tumor targeting probiotic mouse; dipeptidyl peptidase IV human bioluminescence sensing tumor targeting probiotic.

The abnormally expressed peptidases in human tissues are associated with many kinds of cancers. Monitoring of endogenous peptidase activity could allow us for pathophysiol. elucidation and early clin. diagnosis. Herein, we developed a general strategy for bioluminescence (BL) sensing of peptidase activity in vivo based on tumor-targeting probiotics. The probiotic that harbored a luciferase-encoding plasmid was used to target and colonize tumor and provide luciferase for BL imaging. The peptide-based probes Lc and GPc were applied to track leucine aminopeptidase (LAP) and dipeptidyl peptidase IV (DPPIV) activity, resp., by simply adding L-leucine and Gly-Pro dipeptides at the N-terminus of D-cysteine, which were specifically controlled by peptidase cleavage and released free D-cysteine to conduct a subsequent click condensation reaction with 2-cyano-6-hydroxybenzothiazole (HCBT) to produce firefly luciferin in situ, giving rise to a strong BL signal. Neither gene modification of cells of interest nor complicated synthesis was required in this BL system. Encouraged by these advantages, we successfully used our probes to monitor LAP and DPPIV activities in vitro and in vivo, resp. A good linearity between BL and peptidase was obtained in the concentration range of 2.5-40.0 mU/mL with a limit of detection (LOD) of 1.1 mU/mL (55 ng/mL) for LAP and 2.0-40.0 mU/mL with a LOD of 0.78 mU/mL (1.15 ng/mL) for DPPIV, resp. Addnl., approx. 5-fold (LAP) and 10-fold (DPPIV) differences in the BL signal before and after treatment with a specific inhibitor were also obtained for in vivo BL imaging. All these results reflected the potential application value of our probes in BL sensing of peptidase activity. We envision that our strategy may be a useful approach for monitoring a wide range of peptidases in tumors, especially in primary tumors.

Analytical Chemistry (Washington, DC, United States) published new progress about Animal tissue (human). 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

Sun, Shuang; Oliveira, Bruno L.; Jimenez-Oses, Gonzalo; Bernardes, Goncalo J. L. published the artcile< Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells>, Name: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is photoactivation thiol containing drug cancer; cage compounds; cancer; photochemistry; radicals; thiol-ene.

Photoactivated drugs provide an opportunity to improve efficacy alongside reducing side-effects in the treatment of severe diseases such as cancer. Described herein is a photoactivation decaging method of isobutylene-caged thiols through a UV-initiated thiol-ene reaction. The method was demonstrated with an isobutylene-caged cysteine, cyclic disulfide-peptide, and thiol-containing drug, all of which were rapidly and efficiently released under mild UV irradiation in the presence of thiol sources and a photoinitiator. Importantly, it is shown that the activity of histone deacetylase inhibitor largazole can be switched off when stapled, but selectively switched on within cancer cells when irradiated with non-phototoxic light.

Angewandte Chemie, International Edition published new progress about Antitumor agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Name: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

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

Wang, Anni; Li, Xuewei; Ju, Yong; Chen, Dongying; Lu, Jianzhong published the artcile< Bioluminescence imaging of carbon monoxide in living cells based on a selective deiodination reaction>, Application In Synthesis of 2591-17-5, the main research area is bioluminescence imaging carbon monoxide deiodination.

D-Luciferin is a popular bioluminescent substrate of luciferase in the presence of ATP. It was used in luciferase-based bioluminescence imaging and cell-based high-throughput screening applications. Herein, the iodination of D-luciferin was undertaken and explored as a bioluminescence probe without the need for light excitation to sensitively trace and image carbon monoxide (CO) in liver cancer cells. The bioluminescent probe (7′-iodo-luciferin) exhibited excellent selectivity for CO detection in vitro. This new probe could image exogenous and endogenous CO in the luciferase-transfected cancer cells. This new probe might be used for evaluating the roles of CO in various biol. processes.

Analyst (Cambridge, United Kingdom) published new progress about Bioluminescent imaging. 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

Kim, Jun Hyeok; Bell, Laura J.; Wang, Xiao; Wimalasekera, Rinuckshi; Bastos, Hugo P.; Kelly, Krystyna A.; Hannah, Matthew A.; Webb, Alex A. R. published the artcile< Arabidopsis sirtuins and poly(ADP-ribose) polymerases regulate gene expression in the day but do not affect circadian rhythms>, SDS of cas: 2591-17-5, the main research area is Arabidopsis sirtuin PARP gene expression circadian oscillaton; Arabidopsis thaliana; Nicotinamide-adenine dinucleotide; circadian clock; poly(ADP-ribose) glycohydrolase; poly(ADP-ribose) polymerases; sirtuins.

Nicotinamide-adenine dinucleotide (NAD) is involved in redox homeostasis and acts as a substrate for NADases, including poly(ADP-ribose) polymerases (PARPs) that add poly(ADP-ribose) polymers to proteins and DNA, and sirtuins that deacetylate proteins. Nicotinamide, a byproduct of NADases increases circadian period in both plants and animals. In mammals, the effect of nicotinamide on circadian period might be mediated by the PARPs and sirtuins because they directly bind to core circadian oscillator genes. We have investigated whether PARPs and sirtuins contribute to the regulation of the circadian oscillator in Arabidopsis. We found no evidence that PARPs and sirtuins regulate the circadian oscillator of Arabidopsis or are involved in the response to nicotinamide. RNA-seq anal. indicated that PARPs regulate the expression of only a few genes, including FLOWERING LOCUS C. However, we found profound effects of reduced sirtuin 1 expression on gene expression during the day but not at night, and an embryo lethal phenotype in knockouts. Our results demonstrate that PARPs and sirtuins are not associated with NAD regulation of the circadian oscillator and that sirtuin 1 is associated with daytime regulation of gene expression.

Plant, Cell & Environment published new progress about Arabidopsis. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, SDS of cas: 2591-17-5.

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

Ingram, Nicola; McVeigh, Laura E.; Abou-Saleh, Radwa H.; Maynard, Juliana; Peyman, Sally A.; McLaughlan, James R.; Fairclough, Michael; Marston, Gemma; Valleley, Elizabeth M. A.; Jimenez-Macias, Jorge L.; Charalambous, Antonia; Townley, William; Haddrick, Malcolm; Wierzbicki, Antonia; Wright, Alexander; Volpato, Milene; Simpson, Peter B.; Treanor, Darren E.; Thomson, Neil H.; Loadman, Paul M.; Bushby, Richard J.; Johnson, Benjamin R. G.; Jones, Pamela F.; Evans, J. Anthony; Freear, Steven; Markham, Alexander F.; Evans, Stephen D.; Coletta, P. Louise published the artcile< Ultrasound-triggered therapeutic microbubbles enhance the efficacy of cytotoxic drugs by increasing circulation and tumor drug accumulation and limiting bioavailability and toxicity in normal tissues>, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid, the main research area is VEGFR2 SN38 liposome drug delivery circulation bioavailability colorectal cancer; Microbubble; VEGFR2; colorectal cancer; nanoformulation; ultrasound.

Most cancer patients receive chemotherapy at some stage of their treatment which makes improving the efficacy of cytotoxic drugs an ongoing and important goal. Despite large numbers of potent anti-cancer agents being developed, a major obstacle to clin. translation remains the inability to deliver therapeutic doses to a tumor without causing intolerable side effects. To address this problem, there has been intense interest in nanoformulations and targeted delivery to improve cancer outcomes. The aim of this work was to demonstrate how vascular endothelial growth factor receptor 2 (VEGFR2)-targeted, ultrasound-triggered delivery with therapeutic microbubbles (thMBs) could improve the therapeutic range of cytotoxic drugs. Methods: Using a microfluidic microbubble production platform, we generated thMBs comprising VEGFR2-targeted microbubbles with attached liposomal payloads for localised ultrasound-triggered delivery of irinotecan and SN38 in mouse models of colorectal cancer. I.v. injection into tumor-bearing mice was used to examine targeting efficiency and tumor pharmacodynamics. High-frequency ultrasound and bioluminescent imaging were used to visualise microbubbles in real-time. Tandem mass spectrometry (LC-MS/MS) was used to quantitate intratumoral drug delivery and tissue biodistribution. Finally, 89Zr PET radiotracing was used to compare biodistribution and tumor accumulation of ultrasound-triggered SN38 thMBs with VEGFR2-targeted SN38 liposomes alone. Results: ThMBs specifically bound VEGFR2 in vitro and significantly improved tumor responses to low dose irinotecan and SN38 in human colorectal cancer xenografts. An ultrasound trigger was essential to achieve the selective effects of thMBs as without it, thMBs failed to extend intratumoral drug delivery or demonstrate enhanced tumor responses. Sensitive LC-MS/MS quantification of drugs and their metabolites demonstrated that thMBs extended drug exposure in tumors but limited exposure in healthy tissues, not exposed to ultrasound, by persistent encapsulation of drug prior to elimination. 89Zr PET radiotracing showed that the percentage injected dose in tumors achieved with thMBs was twice that of VEGFR2-targeted SN38 liposomes alone. Conclusions: thMBs provide a generic platform for the targeted, ultrasound-triggered delivery of cytotoxic drugs by enhancing tumor responses to low dose drug delivery via combined effects on circulation, tumor drug accumulation and exposure and altered metabolism in normal tissues.

Theranostics published new progress about Bioavailability. 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

Yu, Mohan; Liu, Ya-Jun published the artcile< Same Luciferin in Different Luciferases Emitting Different-Color Light. A Theoretical Study on Beetle Bioluminescence>, Electric Literature of 2591-17-5, the main research area is luciferase bioluminescence luciferin Phrixotrix.

Bioluminescent beetles, firefly, click beetle, and railroad worm, naturally emit different-color light via the identical luciferin and bioluminescence (BL) mechanisms. Railroad worm especially emits two colors of light in its dorsal-lateral and cephalic lanterns. Four computational models of bioluminophore (oLu) in luciferases of red-emitting, yellow-green-emitting, red-emitting with addnl. loop, and red-emitting without C-terminal were built in this paper. To unveil the details of this luciferase effect at the mol. and electronic-state levels, second-order multiconfigurational perturbation calculations were performed following mol. dynamic simulations and time-dependent d. functional calculations for the above four oLu-luciferase systems. Via a systematic anal. on properties of oLu at the first singlet state (S1-oLu) in different luciferases, one clearly see the details of the microenvironment and secondary structure of luciferase affecting the excited-state property of S1-oLu, which ultimately result in the variant color of light emission. Typically, the increase in charge transfer of S1-oLu leads to the longer wavelength BL.

Journal of Chemical Theory and Computation published new progress about Bioluminescence. 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

Saito-Moriya, Ryohei; Nakayama, Jun; Kamiya, Genta; Nobuo Kitada; Obata, Rika; Maki, Shojiro A.; Aoyama, Hiroshi published the artcile< How to select firefly luciferin analogues for in vivo imaging>, Application of C11H8N2O3S2, the main research area is review bioluminescence firefly luciferin analog imaging; bioluminescence imaging; high sensitivity; luciferase; luciferin analogue; multicolor; near-infrared light.

A review. Bioluminescence reactions are widely applied in optical in vivo imaging in the life science and medical fields. Such reactions produce light upon the oxidation of a luciferin (substrate) catalyzed by a luciferase (enzyme), and this bioluminescence enables the quantification of tumor cells and gene expression in animal models. Many researchers have developed single-color or multicolor bioluminescence systems based on artificial luciferin analogs and/or luciferase mutants, for application in vivo bioluminescence imaging (BLI). In the current review, we focus on the characteristics of firefly BLI technol. and discuss the development of luciferin analogs for high-resolution in vivo BLI. In addition, we discuss the novel luciferin analogs TokeOni and seMpai, which show potential as high-sensitivity in vivo BLI reagents.

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

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

Bazhin, Arkadiy A.; Sinisi, Riccardo; De Marchi, Umberto; Hermant, Aurelie; Sambiagio, Nicolas; Maric, Tamara; Budin, Ghyslain; Goun, Elena A. published the artcile< A bioluminescent probe for longitudinal monitoring of mitochondrial membrane potential>, Reference of 2591-17-5, the main research area is bioluminescent probe mitochondria membrane potential.

Mitochondrial membrane potential (ΔΨm) is a universal selective indicator of mitochondrial function and is known to play a central role in many human pathologies, such as diabetes mellitus, cancer and Alzheimer′s and Parkinson′s diseases. Here, the authors report the design, synthesis and several applications of mitochondria-activatable luciferin (MAL), a bioluminescent probe sensitive to ΔΨm, and partially to plasma membrane potential (ΔΨp), for non-invasive, longitudinal monitoring of ΔΨm in vitro and in vivo. The authors applied this new technol. to evaluate the aging-related change of ΔΨm in mice and showed that nicotinamide riboside (NR) reverts aging-related mitochondrial depolarization, revealing another important aspect of the mechanism of action of this potent biomol. In addition, the authors demonstrated application of the MAL probe for studies of brown adipose tissue (BAT) activation and non-invasive in vivo assessment of ΔΨm in animal cancer models, opening exciting opportunities for understanding the underlying mechanisms and for discovery of effective treatments for many human pathologies.

Nature Chemical Biology published new progress about Aging, animal. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Reference of 2591-17-5.

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