Tag: M.W=0-100

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2,4-Dimethyl-1H-pyrrole, is researched, Molecular C6H9N, CAS is 625-82-1, about A near-infrared and lysosomal targeting thiophene-BODIPY photosensitizer: Synthesis and its imaging guided photodynamic therapy of cancer cells, the main research direction is lysosome thiophene BODIPY photosensitizer preparation imaging cancer photodynamic therapy; Lysosomal targeting; NIR photosensitizer; Photodynamic therapy; Singlet oxygen; Thiophene-BODIPY.Recommanded Product: 2,4-Dimethyl-1H-pyrrole.

In this study, a novel NIR and lysosomal targeting thiophene-BODIPY photosensitizer SBOP-Lyso was synthesized to explore its potential applications in photodynamic therapy of A549 cells. In the strategy of designing SBOP-Lyso, S atom in thiophene as well as heavy atom I were introduced to promote ISC efficiency to ensure high singlet oxygen yield. A common lysosome targeted group (M1: 1-(2-morpholinoethyl)-1H-indole-3-carbaldehyde) was linked to SBOP to extend its wavelength to the NIR region. Its absorption peak was at 660 nm (εmax = 5.2 x 104 cm-1 M-1) and its corresponding emission peak was located at 705 nm. Singlet oxygen could be quickly generated by SBOP-Lyso in the presence of 660 nm LED irradiation and the singlet oxygen yield was up to 44.1%. In addition, it also had good biocompatibility and could enter cells or zebrafish in a short time. SBOP-Lyso had negligible dark cytotoxicity (cell survival rate > 80%) and excellent phototoxicity (IC50 = 0.2 μM). DCFH-DA (ROS indicator) proved that SBOP-Lyso could generate singlet oxygen with 660 nm LED irradiation Singlet oxygen produced by SBOP-Lyso could kill cancer cells in PDT process and it had the ability to effectively inhibit A549 cells migration. Besides that, lysosomal colocalization assay showed that it had good lysosomal localization ability (Pearson colocation coefficient, R = 0.93). Considering the above results, SBOP-Lyso as a unique lysosome-targeted photosensitizer with excellent properties would exhibit pos. results in PDT process of cancer cells.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Discovery of a potent glutathione peroxidase 4 inhibitor as a selective ferroptosis inducer, published in 2021-09-23, which mentions a compound: 948552-36-1, mainly applied to chloroacetyl anilino arylacetamide ferroptosis inducer preparation antitumor activity; glutathione peroxidase inhibitor structure activity relationship, Name: 1H-Pyrazole-5-carbaldehyde.

Potent and selective ferroptosis regulators promote an intensive understanding of the regulation and mechanisms underlying ferroptosis, which is highly associated with various diseases. In this study, through a stepwise structure optimization, a potent and selective ferroptosis inducer was developed targeting to inhibit glutathione peroxidase 4 (GPX4), and the structure-activity relationship (SAR) of these compounds I [R1 = allyl, cyclohexyl, allyl, etc.; n = 0 and 1], II [wherein, Het = 1H-pyrazol-3-yl, 2-methylpyrazol-3-yl, 1H-indol-4-yl, etc.] and III [X = N and S; R2 = fluoro, methoxy, 5-methyloxazolyl, etc.] was uncovered. Compound III [X = S; R2 = 5-methyloxazolyl] exhibited outstanding GPX4 inhibitory activity with a percent inhibition up to 71.7% at 1.0 μM compared to 45.9% of RSL-3. At the cellular level, III [X = S; R2 = 5-methyloxazolyl] could significantly induce lipid peroxide (LPO) increase and effectively induce ferroptosis with satisfactory selectivity (the value of 31.5). The morphol. anal. confirmed the ferroptosis induced by III [X = S; R2 = 5-methyloxazolyl]. Furthermore, III [X = S; R2 = 5-methyloxazolyl] significantly restrained tumor growth in a mouse 4T1 xenograft model without obvious toxicity.

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Pyridine – Wikipedia,
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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Chemical Communications (Cambridge, United Kingdom) called Alignment of supramolecular J-aggregates based on uracil-functionalized BODIPY dye for polarized photoluminescence, Author is Zhang, Yongjie; Liu, Ping; Pan, Hongfei; Dai, Haitao; Ren, Xiang-Kui; Chen, Zhijian, which mentions a compound: 625-82-1, SMILESS is CC1=CNC(C)=C1, Molecular C6H9N, Reference of 2,4-Dimethyl-1H-pyrrole.

A BODIPY dye functionalized with uracil-ethynyl groups at the 2,6-positions supramolecularly polymerized into J-aggregates directed by intermol. H-bonds and featured intense absorption and resonant fluorescence. The alignment of J-aggregated chromophores in a thin film was achieved by a rubbing method and polarized luminescence with a dichroic ratio up to 14.3 was obtained.

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Pyridine – Wikipedia,
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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 625-82-1, is researched, SMILESS is CC1=CNC(C)=C1, Molecular C6H9NJournal, Article, Research Support, Non-U.S. Gov’t, Organic & Biomolecular Chemistry called Red fluorescent pyrazoline-BODIPY nanoparticles for ultrafast and long-term bioimaging, Author is Zhang, Yuandong; Zheng, Xiaohua; Zhang, Liping; Yang, Zhiyu; Chen, Li; Wang, Lei; Liu, Shi; Xie, Zhigang, the main research direction is red fluorescent pyrazoline BODIPY nanoparticle bioimaging.Safety of 2,4-Dimethyl-1H-pyrrole.

Fluorescence bioimaging is very significant in studying biol. processes. Fluorescent nanoparticles (NPs) manufactured from aggregation-induced emission (AIE) materials, as promising candidates, have attracted more attention. However, it is still a challenge to explore suitable AIE NPs for bioimaging. Herein, the authors synthesized pyrazoline-BODIPY (PZL-BDP) with a donor and acceptor (D-A) structure by a condensation reaction, cultured its single crystal, and studied its twisted intramol. charge transfer (TICT) and AIE effects. PZL-BDP could self-assemble to form red fluorescent nanoparticles (PZL-BDP NPs) which showed a good fluorescence quantum yield of 15.8% in water. PZL-BDP NPs with excellent stability and biocompatibility exhibited a large Stokes shift (Δλ = 111 nm) which resulted in the reduction of external interference and enhancement of the fluorescence contrast. Furthermore, these nanoparticles could be readily internalized by HeLa cells and they stain the cells in just five seconds, indicating an ultrafast bioimaging protocol. Moreover, long-term tracking fluorescence signals in vivo for ∼12 days were obtained. The bright red fluorescence, ultrafast cell staining ability, and long-term in vivo tracking competence outline the great potential of rational design nanomaterials with AIE characteristics for monitoring biol. processes.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Recommanded Product: 2,4-Dimethyl-1H-pyrrole. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2,4-Dimethyl-1H-pyrrole, is researched, Molecular C6H9N, CAS is 625-82-1, about Synthesis and application of water-soluble reaction-based boron-dipyrromethene (BODIPY) probes for fluorescent detection of peroxynitrite with high selectivity. Author is Zhao, Xiaolong; Li, Na; Liu, Fayu; Gao, Chao; Feng, Jiubiao; Liu, Leping; Guan, Xiaolin; Yan, Na.

Two reaction-based water-soluble boron-dipyrromethene (BODIPY) fluorescent probes, Ac-Phe-BODIPY and Ac-BODIPY, were developed for peroxynitrite (ONOO-) measurement. High sensitivity, low detection limit and excellent selectivity toward ONOO- were obtained for determining reactive oxygen species (ROS) and reactive nitrogen species (RNS). The reaction-based probe Ac-Phe-BODIPY was hydrolyzed into BODIPY-1 which was isolated by column chromatog. and proved by 1H NMR and ESI-MS. The characterization results revealed the photoinduced electron transfer (PET) mechanism which was simultaneously in agreement with d. functional theory (DFT) calculation

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Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Deters, Ria; Kramer, Roland published an article about the compound: 1H-Pyrazole-5-carbaldehyde( cas:948552-36-1,SMILESS:O=CC1=CC=NN1 ).Quality Control of 1H-Pyrazole-5-carbaldehyde. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:948552-36-1) through the article.

The new ligand N,N ‘-bis(pyrazol-3-ylmethyl)-1,2-ethanediamine (L) was prepared Reaction with Cu(II) salts afforded [(L)Cu(NO3)]Cl (1) and {[(L)Cu(ClO4)]2[(pzen-H)2Cu2(ClO4)2]}(ClO4)2 (3) which were characterized by x-ray crystallog. The latter complex was obtained in low yield from a crude sample of L which contained N-(pyrazol-3-ylmethyl)-1,2-ethanediamine (pzen) as an impurity. In the [(L)Cu(X)]+ cations square-pyramidal Cu(II) is in-plane coordinated by tetradentate L, with the anion X in the apical position. The Cu ions in dinuclear [(pzen-H)2Cu2(ClO4)2] are bis(pyrazolate) bridged. In aqueous solution [(L)Cu]2+ is in pH-dependent equilibrium with a dimeric species. By precipitation with NaClO4 both monomeric [(L)Cu(ClO4)2] (2) and dimeric [(L-H)2Cu2(ClO4)2] (4) were isolable at pH 4.5 and pH 8.5, resp. Based on spectroscopic and anal. data probably 4 is a bis(pyrazolate) bridged complex in solution and in the solid state.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2,4-Dimethyl-1H-pyrrole( cas:625-82-1 ) is researched.Reference of 2,4-Dimethyl-1H-pyrrole.Hou, Yuqi; Kurganskii, Ivan; Elmali, Ayhan; Zhang, Huimin; Gao, Yuting; Lv, Lingling; Zhao, Jianzhang; Karatay, Ahmet; Luo, Liang; Fedin, Matvey published the article 《Electronic coupling and spin-orbit charge transfer intersystem crossing (SOCT-ISC) in compact BDP-carbazole dyads with different mutual orientations of the electron donor and acceptor》 about this compound( cas:625-82-1 ) in Journal of Chemical Physics. Keywords: triplet annihilation upconversion delayed fluorescence BOPIDY photoinduced charge transfer. Let’s learn more about this compound (cas:625-82-1).

In order to study the spin-orbit charge transfer induced intersystem crossing (SOCT-ISC), Bodipy (BDP)-carbazole (Cz) compact electron donor/acceptor dyads were prepared Charge transfer (CT) emission bands were observed for dyads showing strong electronic coupling between the donor and the acceptor (coupling matrix elements VDA, 0.06 eV-0.18 eV). Depending on the coupling magnitude, the CT state of the dyads can be either dark or emissive. Equilibrium between the 1LE (locally excited) state and the 1CT state was confirmed by temperature-dependent fluorescence studies. Efficient ISC was observed for the dyads with Cz connected at the meso-position of the BDP. Interestingly, the dyad with non-orthogonal geometry shows the highest ISC efficiency (ΦΔ = 58%), which is different from the previous conclusion. The photo-induced charge separation (CS, time constant: 0.7 ps) and charge recombination (CR, ∼3.9 ns) were studied by femtosecond transient absorption spectroscopy. Nanosecond transient absorption spectroscopy indicated that the BDP-localized triplet state was exceptionally long-lived (602μs). Using pulsed laser excited time-resolved ESR spectroscopy, the SOCT-ISC mechanism was confirmed, and we show that the electron spin polarization of the triplet state is highly dependent on the mutual orientation of the donor and acceptor. The dyads were used as triplet photosensitizers for triplet-triplet-annihilation (TTA) upconversion, and the quantum yield is up to 6.7%. TTA-based delayed fluorescence was observed for the dyads (τDF = 41.5μs). The dyads were also used as potent photodynamic therapy reagents (light toxicity of IC50 = 0.1μM and dark toxicity of IC50 = 70.8μM). (c) 2020 American Institute of Physics.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Barut, Burak; Coban, Ozlem; Yalcin, Can Ozgur; Bas, Huseyin; Sari, Suat; Biyiklioglu, Zekeriya; Demirbas, Umit; Ozel, Arzu published an article about the compound: 2,4-Dimethyl-1H-pyrrole( cas:625-82-1,SMILESS:CC1=CNC(C)=C1 ).Category: pyridine-derivatives. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:625-82-1) through the article.

A new series of BODIPY 3 and 6 with two dimethylamino and diethylamino moieties at their 3,5-positions were prepared via Knoevenagel condensation of BODIPY 2 and 5 with 3,4-bis{3-[3-(dimethylamino)phenoxy]propoxy}benzaldehyde and 4-{3-[3-(dimethylamino)phenoxy]propoxy}benzaldehyde. Water soluble BODIPY-3a and BODIPY-6a were synthesized by treating BODIPY 3 and 6 with an excess of CH3-I in DMF. Singlet oxygen quantum yields, DNA binding and cleavage, topoisomerase II inhibition and photodynamic therapy activities of two cationic BODIPY derivatives (BODIPY-3a and BODIPY-6a) were examined utilizing different methods. The singlet oxygen quantum yield values of compounds were found to be 0.07 and 0.13 in TBS. BODIPY-3a and BODIPY-6a interacted with CT-DNA with Kb values of 5.18±(0.15) × 103 and 2.88±(0.05) × 103 M-1, resp. The agarose gel electrophoresis experiments indicated that BODIPY-3a and BODIPY-6a had marked photocleavage activities on supercoiled plasmid DNA. The topoisomerase II inhibition studies showed that BODIPY-6a had higher inhibitory effect than BODIPY-3a, which was in line with the theor. DNA-topoisomerase complex binding studies via mol. docking method. Based on MTT assay results, the IC50 values of BODIPY-3a and BODIPY-6a ranged from > 100μM to 27.20μM for 24, 48 and 72 h without and with light irradiation Finally, LpBODIPY-6a and NpBODIPY-6a were prepared and their cytotoxic and phototoxic properties were determined using MTT assay. The IC50 values of LpBODIPY-6a were found > 100μM and 33.63μM, while the IC50 values of NpBODIPY-6a were 26.01μM and 5.66μM without/with irradiation The presented studies suggested that nanoparticle formulation was found the most promising delivery vehicle for BODIPY-6a.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: 2,4-Dimethyl-1H-pyrrole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2,4-Dimethyl-1H-pyrrole, is researched, Molecular C6H9N, CAS is 625-82-1, about Radiative lifetime of a BODIPY dye as calculated by TDDFT and EOM-CCSD methods: solvent and vibronic effects. Author is Sia, Rengel Cane E.; Arellano-Reyes, Ruben Arturo; Keyes, Tia E.; Guthmuller, Julien.

The radiative emission lifetime and associated S1 excited state properties of a BODIPY dye are investigated with TDDFT and EOM-CCSD calculations The effects of a solvent are described with the polarizable continuum model using the linear response (LR) approach as well as state-specific methods. The Franck-Condon (FC), Herzberg-Teller (HT) and Duschinsky vibronic effects are evaluated for the absorption and emission spectra, and for the radiative lifetime. The transition energies, spectra shapes and radiative lifetime are assessed with respect to exptl. results. It is found that the TDDFT transition energies are overestimated by about 0.4-0.5 eV, whereas EOM-CCSD improves the vertical emission energy by about 0.1 eV in comparison to TDDFT. The solvatochromic and Stokes shifts are better reproduced by the state-specific solvation methods, which show that these methods are more suited than the LR model to describe the solvent effects on the BODIPY dye. The vibronic effects lead to an increase of the radiative lifetime of about 0.4 to 1.0 ns depending on the theor. approach, which highlights the importance of such effects. Moreover, the HT effects are negligible on both the spectra and lifetime, which demonstrates that the FC approximation is accurate for the BODIPY dye. Finally, the comparison with exptl. data shows that the radiative lifetimes predicted by EOM-CCSD and TDDFT have comparable accuracy.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Name: 2,4-Dimethyl-1H-pyrrole. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2,4-Dimethyl-1H-pyrrole, is researched, Molecular C6H9N, CAS is 625-82-1, about A Nano-BODIPY Encapsulated Zeolitic Imidazolate Framework As Photoresponsive Integrating Antibacterial Agent.

Drug-resistant bacteria challenge the antimicrobial agents and antibacterial strategy. To develop environmental friendly smart technol. for treating pathogens, we report a kind of photoactivated nano-BODIPY (BCNBA@ZIF). First BODIPY compound (BC) was synthesized by coupling phenethyl caffeate (CAPE) with brominated BODIPY through B-O bonds. Next, BC was encapsulated in ZIF-8 together with 2-nitrobenzaldehyde (o-NBA) to form photoactivated BCNBA@ZIF nanoparticles. TEM confirm the structural change of BCNBA@ZIF after illumination. BCNBA@ZIF is less toxic to cells without illumination. Under illumination of blue LED light, the BCNBA@ZIF worked as a photoacid generator initiating the damage of ZIF shell with the release of BC, metal ions, and the production of singlet oxygen for achieving multifunctional antibacterial uses. Therefore, BCNBA@ZIF is a kind of photodriven smart “”Domino”” agent for bacterial inhibition.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem