Benzophenone Derivatives Research Articles

Maternal exposure to benzophenone derivatives and their impacts on offspring's birth outcomes in a Middle Eastern population

Widespread use of benzophenones (BPs), a group of environmental phenolic compounds, is suspected of interfering with human health. The association of prenatal exposure to benzophenone derivatives with birth outcomes including birth weight and length, head, arm and thoracic circumference, abnormalities, corpulence index and anterior fontanelle diameter (AFD) was investigated. Mother-infant pairs of 166 within PERSIAN cohort population in Isfahan, Iran, in the 1st and 3rd trimesters of pregnancy were assessed. Four common benzophenone metabolites including 2,4-dihydroxy benzophenone (BP-1), 2-hydroxy-4-methoxy benzophenone (BP-3), 4-hydroxy benzophenone (4-OH-BP) and 2,2′-dihydroxy-4-methoxy benzophenone (BP-8) were measured in maternal urine samples. The median concentration of 4-OH-BP, BP-3, BP-1 and BP-8 were 3.15, 16.98, 9.95 and 1.04 µg/g Cr, respectively. In the 1st trimester, 4-OH-BP showed a significant correlation with AFD in total infants, decreasing 0.034 cm AFD per a log unit increase of 4-OH-BP. Within the male neonates, 4-OH-BP in the 1st and BP-8 in the 3rd trimester were significantly associated with head circumference and AFD increase, respectively. Among female neonates in the 3rd trimester, increasing 4-OH-BP and BP-3 concentration was correlated with a decrease in birth weight and AFD, respectively. This study demonstrated that all the target BP derivatives can influence normal fetal growth at any age of the pregnancy, nevertheless, to support these findings further studies are needed in a large and different group population.

Three New Benzophenone Derivatives from Selaginella tamariscina.

Six compounds including three new benzophenones, selagibenzophenones D-F (1-3), two known selaginellins (4-5) and one known flavonoid (6), were isolated from Selaginella tamariscina. The structures of new compounds were established by 1D-, 2D-NMR and HR-ESI-MS spectral analyses. Compound 1 represents the second example of diarylbenzophenone from natural sources. Compound 2 possesses an unusual biphenyl-bisbenzophenone structure. Their cytotoxicity against human hepatocellular carcinoma HepG2 and SMCC-7721 cells and inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production in RAW264.7 cells were evaluated. Compound 2 showed moderate inhibitory activity against HepG2 and SMCC-7721 cells, and compounds 4 and 5 showed moderate inhibitory activity to HepG2 cells. Compounds 2 and 5 also exhibited inhibitory activities on lipopolysaccharide-induced nitric oxide (NO) production.

Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities

Ten undescribed benzophenones, schomburginones A−J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their absolute configurations were determined using ECD and single-crystal X-ray diffraction analysis. The isolated metabolites represent benzophenone derivatives containing a modified monoterpene unit, including tri- and tetracyclic skeletons, which are rarely found in genus Garcinia. The cytotoxic evaluation on three cancerous cell lines demonstrated that schomburginone G, schomburginone H, and 3-geranyl-2,4,6-trihydroxybenzophenone were active against HeLa cells with IC50 values in the range of 12.2–15.7 μM, respectively, and selective compared to the non-cancerous L929 cells (SI > 3.5). In addition, the three cytotoxic compounds together with clusiacyclol A showed significant NO inhibitory activity in RAW 264.7 macrophage cells over 85% inhibition without obvious cytotoxicity at a final concentration of 100 μM. The promising activities of these compounds in cytotoxic and anti-inflammatory assays make them attractive for further study in the development of anticancer drugs.

Trust your sunscreen with caution: A literature review on the side effects of sunscreen

Sunscreen use has grown significantly in recent years due to its ability to block harmful ultraviolet (UV) rays and reduce skin problems such as sunburn, aging skin, and immunosuppression. This review examines the ingredients in sunscreen and the effects they have. Substances including oxybenzone, avobenzone, homosalate, octisalate, enzacamene, and benzophenone enter the systemic circulation. The discovery of these substances in plasma and urine sparked concerns about their safety and the requirement for additional study into the long-term consequences they produce. The adverse effects of benzophenone, ecamsule, zinc oxide, titanium oxide, methylisothiazolinone, homosalate, octinoxate, aluminum oxide, and cinnamate derivatives such as octyl methoxycinnamate and octocrylene are also covered in this research. The mechanism of action of UV filters, as well as methods for assessing the effectiveness of sunscreens such as the sun protection factor, persistent pigment darkening, and immune protection factor, is elaborated. This literature review will also discuss the safety and effectiveness of the compounds used in sunscreen formulation as well as any potential health risks and toxicities.

Antioxidative Indenone and Benzophenone Derivatives from the Mangrove-Derived Fungus Cytospora heveae NSHSJ-2.

Seven new polyketides, including four indenone derivatives, cytoindenones A-C (1, 3-4), 3'-methoxycytoindenone A (2), a benzophenone derivative, cytorhizophin J (6), and a pair of tetralone enantiomers, (±)-4,6-dihydroxy-5-methoxy-α-tetralone (7), together with a known compound (5) were obtained from the endophytic fungus Cytospora heveae NSHSJ-2 isolated from the fresh stem of the mangrove plant Sonneratia caseolaris. Compound 3 represented the first natural indenone monomer substituted by two benzene moieties at C-2 and C-3. Their structures were determined by the analysis of 1D and 2D NMR, as well as mass spectroscopic data, and the absolute configurations of (±)-7 were determined on the basis of the observed specific rotation value compared with those of the tetralone derivatives previously reported. In bioactivity assays, compounds 1, 4-6 showed potent DPPH· scavenging activities, with EC50 values ranging from 9.5 to 16.6 µM, better than the positive control ascorbic acid (21.9 µM); compounds 2-3 also exhibited DPPH· scavenging activities comparable to ascorbic acid.

Apoptotic effects of phenols from the twigs and leaves of Garcinia nujiangensis

In order to find potential agents for treating cancer disease in naturally occurring compounds, we conducted a systematic phytochemical investigation on the endemic species of Garcinia nujiangensis. Three new biphenyl derivatives (1–3) and one new polycyclic polyprenylated benzophenone (4), together with four known benzophenone analogues (5–8), have been isolated from the CH2Cl2 extract of the twigs and leaves of G. nujiangensis. Their structures were determined by detailed spectroscopic analyses and comparison with structurally related known analogues. Experimental and calculated ECD method was used to determine the absolute configuration of 1 and 4. Moreover, compounds 5–7 were isolated for the first time from this species. The cytotoxicities of the new compounds were evaluated using HL-60, HepG2, and A549 human cancer cell lines. Compound 4 showed more significant antiproliferative effects against HepG2 cells with an IC50 value of 11.38 ± 0.79 μM than that of three biphenyl derivatives. The morphological features of apoptosis were evaluated in 4-treated HepG2 cells. Compound 4 effectively prevented the cell cycle progression of HepG2 cells in G2 phase. Additionally, western blot analysis indicated that treatment of 4 on HepG2 cells led to decreased expression of anti-apoptotic Bcl-2 and pro-Caspase-3, and increased protein expression of both pro-apoptotic Bax and cleaved PARP with reference to β-actin. Overall, our results suggested that the active polycyclic polyprenylated benzophenone derivatives in the twigs and leaves of G. nujiangensis can be used as a valuable source of bioactive compounds for the pharmaceutical industry.

Light-Assisted Synthesis of Silver and Gold Nanoparticles by New Benzophenone Derivatives.

Benzophenone derivatives were evaluated as new photoinitiators in combination with triethylamine (TEA) and iodonium salt (Iod) for very rapid and efficient formation of metal nanoparticles in an organic solvent, by which silver and gold ions were reduced under light at 419 nm (photoreactor) with an irradiation intensity of 250 microwatts/cm2. The new benzophenone derivatives combined with TEA/Iod salt showed good production of metal nanoparticles (Au0 and Ag0) and a small size of nanoparticles of around 4-13 nm. The photochemical mechanisms for the production of initiating radicals were studied using cyclic voltammetry, where a negative ΔG of around -1.96 eV was obtained, which made the process favorable. The obtained results proved the formation of amine and phenyl radicals, which led to the reduction of gold III chloride or silver ions to the gold and silver NPs. The UV-vis spectroscopy technique was used as a very beneficial tool for the surface plasmon resonance band detection of metal nanoparticles. To sum up the results, we have observed that nanoparticles (NPs) were distributed differently in different photoinitiator systems and the particle size also changed by changing the system of initiation. In comparison to the system alone, not only were the nanoparticles smaller but they were also generated within a shorter period of irradiation time for the system BP\Iod\TEA. Finally, the quenching process of benzophenone fluorescence by the gold and silver nanoparticles was investigated.

Garcinol protects SH-SY5Y cells against MPP+-induced cell death by activating DJ-1/SIRT1 and PGC-1α mediated antioxidant pathway in sequential stimulation of p-AMPK mediated autophagy.

Parkinson's disease (PD), a chronic and progressive neurodegenerative disease, can reduce the population of dopaminergic neurons in the substantia nigra. The cause of this neuronal death remains unclear. 1-Methyl-4-phenylpyridinium ion (MPP+) is a potent neurotoxin that can destroy dopaminergic (DA) neurons and promote PD. Garcinol, a polyisoprenylated benzophenone derivative, was extracted from Garcinia indica and is an important active compound it has been used as an anticancer, antioxidant, and anti-inflammatory, agent and it can suppress reactive oxygen species (ROS) mediated cell death in a PD model. Human neuroblastoma (SH-SY5Y) cells (1 × 105 cells) were treated with MPP+ (1 mM) for 24 h to induce cellular ROS production. The formation of ROS was suppressed by pretreatment with different concentrations of garcinol (0.5 and 1.0μM) for 3h in SH-SY5Y cells. The present study found that MPP+ treatment increased the formation of reactive oxygen species (ROS), and the increased ROS began to promote cell death in SH-SY5Y cells. However, our natural compound garcinol effectively blocked MPP+-mediated ROS formation by activating the DJ-1/SIRT1 and PGC-1α mediated antioxidant pathway. Further findings indicate that the activated SIRT1 can also regulate p-AMPK-mediated autophagy to protect the neurons from the damage it concludes that garcinol sub-sequential regulates intracellular autophagy in this model, and the productive efficacy of garcinol was confirmed by western blot analysis and MitoSOX DCFDA and MTT assays. The results showed garcinol increased protection due to the prevention of MPP+-induced ROS and the promotion of cell survival.

Two new benzophenones from the moss Pogonatum spinulosum

Two new benzophenone derivatives (1 and 2), named Pogonatone C and pogonatone D, were isolated from the moss Pogonatum spinulosum. Their structures were elucidated by spectroscopic data analyses. The cytotoxicity of compounds for HepG2, HCT-116, A-549 and PANC-1 cells line was also evaluated by using the MTT method. Pogonatone C (1) displays high cytotoxicity on PANC-1 cell with IC50 value of 9.2 μM.

Structural Perspective of Benzophenones Targeting Tubulin as Anticancer Agents.

Cancer is the leading cause of death and the most significant determinant of life expectancy in almost every country in this twenty-first century. According to the World Health Organization (WHO), cancer is responsible for the leading cause of death globally. Benzophenone derivatives are found in a variety of naturally occurring compounds which are known to be pharmacologically efficacious against a variety of diseases, including cancer. Microtubules are thought to be a good target for cancer chemotherapies. Microtubule polymerization and depolymerization are induced by a variety of natural, synthetic, and semisynthetic chemicals having a benzophenone nucleus, affecting tubulin dynamics. Several medications that affect microtubule dynamics are in various stages of clinical trials, including Combretastatins (phase II), Vincristine (clinically approved), Paclitaxel (in clinical usage), and epothilone (phase III), and only a few have been patented. Benzophenone derivatives target the colchicine binding site of microtubules, damage them and cause cell cycle arrest in the G2-M phase. Belonging to this class of molecules, phenstatin, a potent inhibitor of tubulin polymerization, has shown strongly inhibit cancer cell growth and arrest the G2/M phase of the cell cycle by targeting the colchicine binding site of microtubules. In the present manuscript, we described the benzophenone as tubulin polymerization inhibitors, their Structure-Activity Relationships (SARs) and molecular docking studies that reveal its binding affinity with the colchicine binding site.

Dihydrolevoglucosenone (Cyrene™), a new possibility of an environmentally compatible solvent in synthetic organic electrochemistry.

Dihydrolevoglucosenone (DLG or Cyrene™) solvent is a green dipolar solvent produced from cellulose waste. Different studies have demonstrated that it can successfully replace dipolar solvents, such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and N-methylpyrrolidinone (NMP), in a variety of chemical reactions. In this paper, the first application of DLG in organic electrosynthesis is described, with results of its use in the electrochemical reduction of benzophenone derivatives (ca. E = -1.75 V vs. Ag/AgCl), as a greener alternative to other dipolar solvents with environmental concerns. Conductivity measurements show that the solvent presents conductivity and viscosity limitations that can be overcome by using EtOH as a cosolvent. The DLG/EtOH mixture resulted in a convenient solvent to carry out galvanostatic electroreductions of starting materials that exhibit high potential value. Furthermore, the reaction pathway (1e- or 2e-) was found to be dependent on the supporting electrolyte used; TBABF4 favored 2e- reduction to the corresponding alcohol (52-85%), whereas LiClO4 promoted C-C pinacolic coupling (47-70%).

Benzophenone Derivatives with Histamine H3 Receptor Affinity and Cholinesterase Inhibitory Potency as Multitarget-Directed Ligands for Possible Therapy of Alzheimer's Disease.

The multitarget-directed ligands demonstrating affinity to histamine H3 receptor and additional cholinesterase inhibitory potency represent a promising strategy for research into the effective treatment of Alzheimer's disease. In this study, a novel series of benzophenone derivatives was designed and synthesized. Among these derivatives, we identified compound 6 with a high affinity for H3R (Ki = 8 nM) and significant inhibitory activity toward BuChE (IC50 = 172 nM and 1.16 µM for eqBuChE and hBuChE, respectively). Further in vitro studies revealed that compound 6 (4-fluorophenyl) (4-((5-(piperidin-1-yl)pentyl)oxy)phenyl)methanone) displays moderate metabolic stability in mouse liver microsomes, good permeability with a permeability coefficient value (Pe) of 6.3 × 10-6 cm/s, and its safety was confirmed in terms of hepatotoxicity in the HepG2 cell line. Therefore, we investigated the in vivo activity of compound 6 in the Passive Avoidance Test and the Formalin Test. While compound 6 did not show a statistically significant influence on memory and learning, it showed analgesic properties in both acute (ED50 = 20.9 mg/kg) and inflammatory (ED50 = 17.5 mg/kg) pain.

Host-guest doping induced excited state energy transfer for efficient room temperature phosphorescence emission

The 1,8-naphthalimide derivatives as the guest and the benzophenone (BP) analogues bis(4-chlorophenyl)methanone (BP2C) and bis(4-fluorophenyl)methanone (BP2F) benzophenone derivatives as the host, we constructed a series of novel doping systems with fluorescence and room temperature phosphorescence (RTP) dual emission. The steady-state spectroscopy, ultrafast spectroscopy techniques, and theoretical calculations indicate that Förster resonance energy transfer (FRET) between singlet states between host and guest components enables energy redistribution in doped systems. At the same time, the Dexter energy transfer (DET) between the triplet states realizes the obvious absorption of the excited triplet state of the guest, resulting in the long-lived room temperature phosphorescence of the doped system. Doping materials have unlimited potential for information storage and anti-counterfeiting by exploiting the properties of photo activation.

Polarity- and Pressure-Induced Emission from a Benzophenone-Based Luminophore.

Since strong polarity usually causes emission quenching, materials with polarity-induced emission (PIE) are rarely reported despite their important applications in polar environments. Herein, an N-phenylcarbazole-substituted benzophenone derivative (BP-3-Cz) with a twisted electron donor-acceptor (D-A) structure is synthesized. The incorporation of heteroatoms into the twisted π-conjugated D-A backbone simultaneously endows BP-3-Cz with obvious polarity- and pressure-induced emission. Spectral analysis, X-ray diffraction, differential scanning calorimetry, and quantum chemical calculation results confirm that BP-3-Cz has special optical features related to the molecular conformation change and excited state turning to planarized intramolecular charge transfer with an increase in polarity or applied pressure. These findings contribute to the understanding of the PIE mechanism and the design of new PIE materials.

Excitation‐Dependent and Efficient Phosphorescence Based on Benzophenone Derivatives

AbstractThe design of organic molecules with high photoluminescence quantum efficiency and adjustable emission colors has led to the development of high‐performance optoelectronic devices. However, the task of generating color‐tunable luminescence originating from different excited states has achieved limited success. Here, a design strategy is presented for improving phosphorescence quantum efficiency and extending emission spectral range by introducing high luminous acenes in benzophenone derivatives. The experimental data reveal that the maximum phosphorescence efficiency of the designed molecule can reach 84% in solution and 61% in crystals, which is the most efficient benzophenone phosphor so far. Importantly, the excited states can be selectively expressed by varying the excitation wavelengths, including thermally activated delayed fluorescence (TADF) from T2 to S1 excited state, and dual phosphorescence from T2 and T1 excited states. The design strategy of using rigid acenes to suppress nonradiative transition provides an opportunity to improve phosphorescence efficiency comparable with fluorescence efficiency, presenting great potential in high‐performance optoelectronic devices.

Nearest-Neighbour and Non-Nearest-Neighbour Non-Covalent Interactions between Substituents in the Aromatic Systems: Experimental and Theoretical Investigation of Functionally Substituted Benzophenones

Benzophenone derivatives exhibit not only biological activity but also act as photo initiator and UV blocker. We carried out experimental and theoretical thermochemical studies of hydroxy- and methoxy-substituted benzophenones. Standard molar enthalpies of vaporisation were obtained from the temperature dependence of vapour pressures measured by the transpiration method. The thermodynamic data on phase transitions available in the literature (crystal-gas, crystal-liquid, and liquid-gas) were also collected and evaluated. High-level quantum chemical methods G3MP2 and G4 were used to estimate the standard molar enthalpies of formation of substituted benzophenones in the gas phase and establish agreement between experimental and theoretical results. The application of the "centrepiece" group-contribution approach to hydroxy- and methoxy-substituted benzophenones was demonstrated. A quantitative assessment of the hydrogen bond was carried out using various approaches based on experimental data and quantum chemical calculations.

Study on Synthesis, Optical properties and Application of Benzophenone derivatives

AbstractIn this study, the mono‐substituted and di‐substituted benzophenone derivatives containing the ester group were synthesized by the reaction of dihydroxy benzophenone with acyl chloride. Their structures were characterized by 1H NMR and 13C NMR and their optical properties and application in ultraviolet curable coatings were studied. The mono‐substituted compounds can be used as UV absorbers and do not participate in the curing of the free radical system during UV‐curing, enhancing the light stability of coatings and cured coatings and facilitating the storage of UV‐curable coatings. The di‐substituted compounds can be used as photoinitiators for ultraviolet curable coatings and show good film morphology.

Chemical Constituents of the Roots of Polygala tenuifolia and Their Anti-Inflammatory Effects

Increasing scientific evidence has demonstrated that the roots of Polygala tenuifolia Willd. have pharmacological effects related to anti-inflammation. Therefore, the aim of this study is to investigate the chemical constituents from P. tenuifolia roots as anti-inflammatory drug candidates. In the present work, twenty-three compounds were isolated from P. tenuifolia roots, including three saponins (1-3), ten phenylpropanoid sucrose esters (4-12), one benzoic acid sugar ester derivative (13), four xanthones (14-17), two hydroxy benzophenone derivatives (18 and 19), two phenolic derivatives (20 and 21), and two ionones (22 and 23). All isolates were tested for their inhibitory effects of LPS-stimulated NO and PGE2 production in RAW 264.7 macrophages. Among these, 3-O-(3,4,5-trimethoxy-cinnamoyl),6'-O-(p-methoxybenzoyl) sucrose ester (TCMB; 11) together with compounds 3 and 21 exhibited significant inhibitory effects on NO production, while TCMB and compounds 17, 19, and 21 showed strong inhibitory effects on PGE2 production. Specifically, TCMB (11) downregulated the protein levels of iNOS and COX-2 in LPS-induced RAW 264.7 macrophages. In addition, TCMB (11) dose-dependently diminished the relative mRNA expression levels of iNOS, PGE2, and proinflammatory cytokines (TNF-α, IL-1β, and IL-6). A molecular docking study showed that TCMB (11) has strong binding affinities with iNOS and COX-2.

Recent Advances in Organic Room-Temperature Phosphorescence of Heteroatom (B/S/P)-Containing Chromophores

Recent Advances in Organic Room-Temperature Phosphorescence of Heteroatom (B/S/P)-Containing Chromophores

The Use of Factorial Planning in the Investigation of Structural Electronics Property for the Rational Design of Benzophenone Derivatives

Human exposure to ultraviolet (UV) radiation leads photochemical excitation processes in the skin, causing problems to human health. The use of photoprotectors helps to minimize these intrinsic hazards. Benzophenone molecules stand out for the absorption of energy in the UVA and UVB range and structural changes in these, it is an area of ​​interest to obtain safer and more effective molecules. This work applied the full factorial design methodology 24 in an investigation by molecular modeling using semi-empirical method PM7, in order to evaluate the impact generated on the decrease of the energy GAP with the insertion of OH (level +) and H (level –-). The results showed unfavorable and favorable contributions between interactions and in the main effect, and the compounds disubstituted in ortho and para position for the same aromatic ring showed a better percentage of contribution, indicating that these conditions are relevant for greater reactivity compared to the others. Thus, we conclude that the use of the experimental planning methodology is an ally in obtaining information for planning new protective filtersmore stable and safe.