Antiproliferative, apoptotic, and antimutagenic properties of stem bark and seed fractions of Polyalthia cerasoides (Roxb.).

AIMS: The aim was to compare the anticancer and antimutagenic potency of Polyalthia cerasoides seeds and stem bark. AIM OF THE STUDY: The aim of this study was to investigate the antiproliferative, apoptotic, antioxidation to DNA, and antimutagenic activity of alcoholic (PS-1 and PS-3) and petroleum ether (PS-2 and PS-4) stem bark and seed fractions of P. cerasoides. METHODS: P. cerasoides stem bark and seeds were extracted with ethanol: water mixture (9:1 ratio v: v) and fractionated with petroleum ether. Fractions were investigated for antiproliferative effect using cell by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide, a tetrazole assay (cell line used liver [HepG2] and cervical [HeLa] cancer cell lines), DNA damage protection using hydroxyl radical and antimutagenic effect using chromosome aberration test. RESULTS: PS-1 (IC50 10 µg/ml) and PS-3 (IC50 11 µg/ml) showed maximum antiproliferative activity against HepG2 cell lines, whereas, PS-1 (IC50 10 µg/ml), PS-2 (IC50 24 µg/ml), and PS-3 (IC50 11 µg/ml) showed better antiproliferative activity against HeLa cell lines. PS-3 and PS-4 were protective against oxidation to the supercoiled DNA molecule. Further, petroleum ether extract of both seed (PS-2) and stem bark (PS-4) showed good antimutagenicity as revealed by the less chromosomal aberrations compared to PS-1 and PS-3 fractions. CONCLUSIONS: This study demonstrated the beneficial effect of fractions against oxidation of DNA, antiproliferative, apoptotic, and antimutagenic activity. Probably, this property would be attributable by their phenolic and steroid constituents. Therefore, this plant could be used as a potential source of nutraceutical agents.

Aggregation induced emission based active conjugated imidazole luminogens for visualization of latent fingerprints and multiple anticounterfeiting applications.

Aggregation-induced emission based organic heterocyclic luminogens bearing conjugated electronic structures showed much attention due to its excellent fluorescence in aggregation state. In this communication, a novel conjugated blue light emitting imidazole molecule is synthesized by one pot multicomponent reaction route is reported for the first time. The prepared molecule exhibits a strong fluorescence in aggregation state with exceptional properties, such as high purity, inexpensive, eco-friendly, large scale production, high photostability, etc. By considering these advantages, a new fluorescence based platform has been setup for in-situ visualization of latent fingerprints and its preservation by spray method followed by Poly(vinyl alcohol) masking. A clear and well defined fluorescence fingerprint images are noticed on variety of surfaces by revealing level 1-3 ridge features upon ultraviolet 365 nm light exposure. The dual nature of binding specificity as well as excellent fluorescence properties permits the visualization of latent fingerprints for longer durations (up to 365 days) with superior contrast, high sensitivity, efficiency, selectivity and minimal background hindrance. We further fabricated unclonable invisible security ink for various printing modes on valuable goods for protection against forging. The developed labels are displaying uniform distribution of ink and exceptional stability under various atmospheric environments. The development of long preservative information using aggregation-induced emission based luminogen opens up a new avenue in advanced forensic and data security applications.

Sensing and sensitive visualization of latent fingerprints on various surfaces using a versatile fluorescent aggregation-induced emission-based coumarin derivative.

The marked rise in criminal activity in society has made a difficult task for forensic scientists who aim to track any crime scene effectively, therefore visualization of latent fingerprints (LFPs) plays an increasingly vital role in forensics. In the present report, a highly sensitive solvatochromism, aggregation-induced emission-based 2-(4-nitrophenyl)-3H-benzocoumarin fluorescent dye (CFD) was fabricated using an ultrasonication protocol. The fluorescence properties of the CFD were analyzed using fluorescence spectrophotometer. The CFD produced a greenish yellow emission in solid and fluid states. An in-depth visualization of LFPs showed detailed ridge patterns under normal and ultraviolet light sources (254 and 365 nm) due to the excellent chemisorption of CFD onto the ridge patterns on the finger. All three types of ridge details were visualized without any background interference when using a simple and quick powder dusting method. Results revealed that, the present fluorescent dye can be used successfully for detection of latent fingerprints (LFPs) on various nonporous substrates surfaces, in organic light-emitting diodes applications (OLEDs), and for electrochemical sensing.

Crystal structure and photoluminescent properties of bis-(4'-chloro-2,2':6',2''-terpyrid-yl)cobalt(II) dichloride tetra-hydrate.

In the title hydrated complex, [Co(C15H10ClN3)2]Cl2·4H2O, the complete dication is generated by symmetry. The CoN6 moiety shows distortion from regular octa-hedral geometry with the trans bond angles of two N-Co-N units being 160.62 (9)°. In the crystal, O-H⋯Cl and C-H⋯O inter-actions link the components into (001) sheets. The title compound exhibits blue-light emission, as indicated by photoluminescence data, and a HOMO-LUMO energy separation of 2.23 eV was obtained from its diffuse reflectance spectrum.

New design of highly sensitive AIE based fluorescent imidazole derivatives: Probing of sweat pores and anti-counterfeiting applications.

A novel aggregation induced emission based 2-(1-(3, 5-bis(trifluoromethyl)phenyl)-4,5-diphenyl-1H-imidazol-2-yl) phenol (4) (IMD) fluorescent tags (FTs) was designed by simple acid catalyzed five-member N-heterocyclic ring forming reaction process. Powder X-ray diffraction results showed mechanofluorochromic properties of IMD FTs are easily reversible under external force due to the decrease in crystallinity. These IMD FTs also exhibits strong cyan-blue luminescence in solid state with high quantum efficiency. Detailed investigation of latent fingerprints (LFPs) showed permanent, immutable and unique pores that are distributed on the ridges. The visualization of such sweat pores opens new avenue in the field of forensic science. Hence, the prepared IMD FTs exhibit excellent Lipophicity (LP) properties, which endorse its possible applications for the visualization of sweat pores present in the LFPs. The LFPs visualized by IMD FTs exhibit excellent efficiency, sensitivity, selectivity, low background hindrance and less toxicity. The obtained result evident that the prepared FT and followed technique opens possible applications for the visualization of LFPs on various porous/semi-porous/non-porous surfaces under UV 365 nm light.

Crystal structure of 8-eth-oxy-3-(4-nitro-phen-yl)-2H-chromen-2-one.

In the title compound, C17H13NO5, the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitro-phenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihedral angle of 4.3 (3)°. The eth-oxy group is inclined to the coumarin ring plane by 4.1 (2)°. Electron delocalization was found at the short bridging C-C bond with a bond length of 1.354 (2) Å. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming sheets in the bc plane. The sheets are linked via π-π stacking [centroid-centroid distances = 3.5688 (13) and 3.7514 (13) Å], forming a three-dimensional structure.

Crystal structure of ethyl 2-(2,4,5-tri-meth-oxy-phen-yl)quinoline-4-carboxyl-ate.

In the title compound, C21H21NO5, the dihedral angle between the quinoline ring system (r.m.s. deviation = 0.028 Å) and the tri-meth-oxy-benzene ring is 43.38 (5)°. The C atoms of the meth-oxy groups deviate from their attached benzene ring by -0.396 (2), -0.049 (2) and 0.192 (2) Šfor the ortho-, meta- and para-substituents, respectively. The pendant ethyl chain is disordered over two orientations in a 0.527 (5):0.473 (5) ratio. A short intra-molecular C-H⋯O contact closes an S(6) ring. In the crystal, inversion dimers linked by pairs of weak C-H⋯O inter-actions generate R 2 (2)(6) loops. The dimers are linked by further C-H⋯O inter-actions to generate [1-10] chains.

Synthesis, growth and characterization of a new promising organic nonlinear optical crystal: 4-Nitrophenyl hydrazone.

4-Nitrophenyl hydrazone single crystals were grown by slow evaporation of solvent method using acetone as a solvent. The grown crystals were subjected to various characterizations such as X-ray diffraction studies, UV-visible studies, thermogravimetric analysis and differential thermal analysis (TGA/DTA) and second harmonic generation (SHG). The cell parameters were calculated by using single crystal XRD measurement and the crystal system was found as orthorhombic with non-centro-symmetric space group Pca21. The crystallinity of the grown crystal was confirmed by powder X-ray diffraction analysis. The Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) studies confirmed the presence of functional groups in the sample. The optical transmittance spectrum shows that the crystal is transparent in the visible wavelength range. The scanning electron microscopy (SEM) was used to study the surface morphology of the grown crystal. The chemical composition of the grown crystal was confirmed by energy dispersive X-ray (EDX) analysis. The TGA/DTA results showed that the material is stable up to 146°C. The NLO property of the crystal was confirmed by Kurtz and Perry method and SHG conversion efficiency is 15.39 times when compared to KDP crystal.

Crystal structure of ethyl 6-bromo-2-[(E)-2-phenyl-ethen-yl]quinoline-4-carboxyl-ate.

In the title compound, C20H16BrNO2, the dihedral angle between the quinolone ring system mean plane (r.m.s. deviation = 0.018 Å) and the phenyl ring bridged by the ethynyl group, is 25.44 (14)°. There is an intra-molecular C-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds forming chains propagating along the b-axis direction.

Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one.

In the title compound, C14H17FN2O, the 1,2,3,4-tetra-hydro-pyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methyl-ene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N-C bond distance [1.349 (3) Å] is substanti-ally shorter than the sum of the covalent radii (d cov: C-N = 1.47 Šand C=N = 1.27 Å), which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming sheets lying parallel to (10-1). These two-dimensional networks are linked via C-H⋯F hydrogen bonds and C-H⋯π inter-actions, forming a three-dimensional structure.

Crystal structure of cis-1-(2-methyl-1,2,3,4-tetra-hydro-quinolin-4-yl)azepan-2-one.

In the title compound, C16H22N2O, the azepan-2-one ring adopts a chair conformation, while the 1,2,3,4-tetra-hydro-pyridine ring adopts a half-chair conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming supra-molecular chains propagated along [10-1], with weak C-H⋯O inter-actions occurring between the chains.

Ethyl 5-bromo-naphtho-[2,1-b]furan-2-carboxyl-ate.

In the title compound, C(15)H(11)BrO(3), the dihedral angle between the naphtho-furan ring system (r.m.s. deviation = 0.022 Å) and the side chain is 4.50 (2)°. In the crystal, short Br⋯Br [3.4435 (7) Å] contacts propagating along [010] in a zigzag manner and weak π-π inter-actions [shortest centroid-centroid separation = 3.573 (2) Å] directedalong [100] are observed.

An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines.

4,5-Dihydroisoxazoles continue to attract considerable interest due to their wide spread biological activities. Here, we identify an efficient protocol for the preparation of 4,5-dihydroisoxazoles (2-isaxazolines) (4a-g) from quinolinyl chalcones. The nucleolytic activities of synthesized compounds were investigated by agarose gel electrophoresis. All these compounds were showed the remarkable DNA cleavage activity (concentration dependent) with pUC19 DNA at 365nm UV light. The DNA cleavage activity was significantly enhanced by the presence of iminyl and carboxy radicals of DIQ.

Synthesis and DNA cleavage studies of novel quinoline oxime esters.

New 2-chloro-3-formyl quinoline oxime esters were synthesized by the reaction of 2-chloro-3-formyl quinoline oximes with various benzoyl chlorides in the presence of triethyl amine and dichloromethane at 0°C. The DNA photo cleavage studies of some new oxime esters were investigated by neutral agarose gel electrophoresis at different concentrations (40µM and 80µM). Analysis of the cleavage products in agarose gel indicated that few of quinoline oxime esters (3d-i) converted into supercoiled pUC19 plasmid DNA to its nicked or linear form.

Analgesic, Antibacterial and Antiviral Activities of 2-(5-Alkyl-1,3,4-oxadiazol-2-yl)-3H-benzo[f]chromen-3-ones.

A novel series of 2-(5-alkyl-1,3,4-oxadiazol-2-yl)-3H-benzo[f]chromen-3-ones (4a-e) have been evaluated for analgesic, antibacterial and antiviral activities. Analgesic activity was carried out using acetic acid-induced writhing method in Swiss albino male mice. The antibacterial activity was performed against Gram-positive and Gram-negative clinical strains by agar well diffusion method. The in vitro antiviral activity was carried out against camelpox and buffalopox viruses. The analgesic activity exhibited by the compounds 4a, 4c and 4d were found to be more significant compared to the standard. The bacterial activity was determined by the inhibition of growth of the organism by the drugs at different concentrations. All the compounds showed significant activity when compared with the drug ciprofloxacin. The in vitro antiviral activity of the compound 4b tested against camelpox and buffalopox viruses revealed no activity when tested at concentrations of 250 µg. The compound 4b did not alter the titres of both the viruses and the titres remain, respectively, 10(6.5) TCID50 and 10(6.74) TCID50 per ml for camelpox vaccine virus and buffalopox vaccine virus. However, the compounds 4a-e showed significant analgesic and antibacterial activities.

N-(Phenyl-sulfon-yl)naphtho-[2,1-b]furan-1-carboxamide.

In the title compound, C(19)H(13)NO(4)S, the mol-ecule is twisted at the S atom with a C-S-N-C torsion angle of -65.2 (2)° between the benzene ring and the -SO(2)-NH-C=O segment. The dihedral angle between the benzene and the naphtho-furan ring system is 83.3 (1)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains running along the c axis. An intra-molecular N-H⋯O(furan) inter-action is also observed.

Adaptogenic and in vitro antioxidant activity of flavanoids and other fractions of Argyreia speciosa (Burm.f) Boj. in acute and chronic stress paradigms in rodents.

Argyreia speciosa (sweet) (Burm.f.) Boj. is an Ayurvedic rasayana plant used as an adaptogen. The present study reports the investigations done on the adaptogenic property of ethanol (EtAS; 100 and 200 mg/kg; po), ethyl acetate (EAAS; 100 and 200 mg/kg; po) fraction and flavanoids such as quercetin and kaempferol (25 mg/kg; po) of the root. Immobilization induced acute stress (AS; 3 days) and chronic stress (CS; 7 days) and swimming induced stress models were used to screen the anti-stress effect of the plant fractions and isolated flavanoids. The tested doses of EtAS and isolated flavanoids were able to produce significant effects in normalizing altered serum biochemical parameters and the severity of ulcer in both AS and CS models. Higher dose of EtAS, quercetin and kaempferol (25 mg/kg; po) were found to be significant in restoring the hypertrophy of adrenal gland and atrophy of spleen and thymus gland only in CS model. Greater swimming time was noted in the mice pretreated with tested doses of flavanoids and EtAS. In addition, levels of adrenal ascorbic acid and cortisol were restored compared to stress control group. EtAS exhibited significant scavenging effect of DPPH, hydroxyl radical and LPO. Thus, EtAS, quercetin and kaempferol are capable of increasing the capacity to tolerate non-specific stress in experimental animals, as evident from restoration of large number of parameters in the stress models studied. Bioactivity of EtAS may be due to the synergetic action of isolated flavanoids. Improvement in stress markers may be due its prolong effect of resistance to stress and partly due to free radical scavenging activity.

Antiproliferative, apoptotic and antimutagenic activity of isolated compounds from Polyalthia cerasoides seeds.

Phytochemical investigation of the petroleum ether extract fraction of Polyalthia cerasoides seeds led to the isolation of two phytosterols (alpha-spinasterol and spinasterol) and a clerodane di-terpenoid. The structures of these compounds were elucidated using IR, (1)H-NMR, (13)C-NMR and Mass spectral analysis. Further, these compounds were tested for antiproliferative action against CACO-2 cell line and apoptotic action was determined by nuclear staining and DNA fragmentation analysis. The results showed that the compounds exhibited antiproliferative action at various concentrations with an IC(50) value of 28.6+/-4.34nM/ml, 57.7+/-6.81nM/ml and 60.0+/-7.10nM/ml for clerodane diterpenoid, spinasterol and alpha-Spinasterol respectively. Furthermore, the isolated compounds were screened for antimutagenic effect against methylmethane sulfonate (MMS) induced mutation. Phytosterols showed protective effect, whereas clerodane diterpenoid was less effective to MMS induced chromosomal aberrations. Our research contributes to the characterization of phytochemical constituents and to understand the ability of these compounds to antiproliferative and antimutagenic responses from the seed extracts.

Ethyl 3-oxo-3H-benzo[f]chromene-2-carboxyl-ate.

In the title compound, C(16)H(12)O(4), the chromene ring system is almost planar [maximum deviation = 0.026 (1) Å] and makes dihedral angles of 1.24 (9) and 26.5 (2)° with the fused benzene ring and the plane of the ethyl carboxyl-ate group, respectively.

Antimicrobial activity of flavanoid sulphates and other fractions of Argyreia speciosa (Burm.f) Boj.

Antimicrobial activity of flavanoid sulphates and different fractions of A. speciosa root was studied against bacteria, fungi and Mycobacterium tuberculosis H37 Rv sensitive strain by in vitro and in vivo assays. Flavanoid sulphates such as quercetin 3'7 di-O methyl 3- sulphate and kaempferol 7-O methyl 3-sulphate were isolated from the n-butanol fraction of 80% methanolic extract of the plant. The structures of the isolated flavanoids were confirmed by spectral studies. Ethyl acetate (EAAS) fraction and flavanoid sulphates inhibited the growth of M. tuberculosis Rv sensitive strain at MIC values 50 and 25 microg/ml, respectively. Ethanolic fraction (EtAS) showed significant inhibition of gram positive organism with a MIC of 31.25 microg/ml. More inhibition was observed with a less MIC (2 microg/ml) for flavanoid sulphates against Klebsiella pneumoniae, a gram negative organism and it is almost comparable with the standards. Interestingly, chloroform fraction alone exhibited significant antifungal activity with a MIC of 100 microg/ml. A synergistic effect between flavanoids sulphates and commercially available antitubercular drugs was observed with FIC index of 0.443 +/- 0.245, 0.487 +/- 0.247 for isoniazid and 0.468 +/- 0.333, 0.417 +/- 0.345 for rifampicin, whereas EAAS fraction showed partial synergistic effect. A synergistic effect was observed for EAAS fraction and flavanoids sulphates with FIC index < 0.5 with antibiotics. Hemolysis assay on RBCs suggested that EAAS and flavanoids sulphates exhibited least cellular toxicity to erythrocytes as compared to chloramphenicol. In vivo studies in mice infected with K. pneumoniae demonstrated that on day 10 post treatment of different fractions and isolated compounds of A. speciosa, about 60% of the animals treated with EAAS, 70% of animals treated with flavanoids sulphates and 40% of animals treated with EtAS were survived.