Person: YALÇIN, BAHATTİN
Loading...
Email Address
Birth Date
Research Projects
Organizational Units
Job Title
Last Name
YALÇIN
First Name
BAHATTİN
Name
16 results
Search Results
Now showing 1 - 10 of 16
Publication Metadata only Yeni metil (7-Hidroksi-8-Metil-2-Okso-2HBenzopiran-4-Yl) asetat kumarin içeren ftalosiyaninin kimyasal özelliklerinin incelenmesi(2022-09-28) DİCLE, CANSU; GÖRGÜLÜ, AHMET ORHAN; YALÇIN, BAHATTİN; ÖZDEMİR, MÜCAHİT; DOĞAN Y., DİCLE C., GÖRGÜLÜ A. O., YALÇIN B., BULUT M., ÖZDEMİR M.Halkasında karbon dışında atomlar olan ve oksijen bileşiklerinden meydana gelen büyük heterosiklik aromatik yapılar Kumarin (Coumarine) olarak tanımlar. Kumarin, adını 1820 yılında August Vogel tarafından izole edildiği tonka fasulyesinin (Dipteryx odorata Willd, Fabaceae) sınıf adı olan “coumarou” kelimesinden almıştır. IUPAC adı, 2H-kromen-2-on veya 2H-1-benzopiron-2-on’dur [1,2]. Kumarin ve türevleri doğada yaygın olarak; lavanta, tatlı yonca otu ve meyan kökü gibi bitkilerde; çilek, kiraz, kayısı ve tarçın gibi yiyeceklerde bulunmaktadır [3]. Kapalı formülü C9H6O2’dir. Mol kütlesi 146,14 g/mol, erime noktası 69- 71 °C ve kaynama noktası 301 °C’dir [4]. Kumarinler, absorbsiyon spektrumu ile iyi tanımlanırlar ve ultraviyole ışıkla uyarılınca karakteristik bir floresans gösterir. Ayrıca geniş bir fizyolojik aktiviteye sahiptirler [5]. Kumarin türevleri; yüksek floresans kuantum verimi, büyük kayma, mükemmel ışık stabilitesi ve düşük toksisite gibi birçok avantaja sahiptir [6]. Kumarin sentezlemede kullanılan metodlardan en yaygın olanları; Perkin, Pechmann, Knoevenagel, Reformatsky ve Witting Kondenzasyon reaksiyonlarıdır [7]. Yüksek simetriye sahip dört iminoizoindol ünitesi içeren 18 π elektronlu aromatik makrosiklik yapılar olan ftalosiyaninler, sahip oldukları bu π-elektron delokalizasyonu özelliği nedeni ile olağanüstü optik ve elektriksel davranışlar gösteren kimyasal ve termal olarak dayanıklı bileşiklerdir. İlk sentezlenen bakır ftalosiyanin molekülü merkez metale bağlı klor atomu sayısının arttırılması ile maviden yeşile doğru giden bir renk değişimi göstermiştir. Çoğu ftalosiyanin bileşiği yüksek vakumda buharlaştırılabilip, süblimleştirilebilen bileşiklerdir. Öte yandan termal kararlılıkları sebebiyle çoğunun erime noktası yoktur [8]. Bugüne kadar ftalosiyaninlerde merkez atom olarak 70‘den fazla farklı element kullanılmıştır. Ftalosiyanin ligandı metallerin hemen hepsiyle koordine edilebilir.Publication Metadata only Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties(ELSEVIER SCIENCE SA, 2021) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Koksoy, Baybars; Yalcin, Bahattin; Taskin, Turgut; Selcuki, Nursel Acar; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted lutetium(III) phthalocyanine compounds were synthesized, characterized and their photochemical, theoretical, and antioxidant properties were examined. All complexes were characterized by common spectroscopic methods such as FT-IR, UV?vis, 1H NMR, MALDI-TOF-MS and elemental analysis as well. Geometry optimization of phthalocyanine compounds was calculated in the B3LYP functional using 6-31G (d, p) + SDD basis set of the Density Functional Theory. Aggregation, singlet oxygen generation, and photodegradation behavior under light irradiation of the complexes (1?4) were investigated in dimethylformamide. The three phthalocyanine compounds (1, 2, and 4) showed a high level of singlet oxygen efficiency were compared with the unsubstituted zinc(II) and lutetium(III) phthalocyanine compounds because their quantum yield values were found to be over 0.80. The radical cation scavenging activities of the compounds 3 (120.344 mM trolox/mg) and 4 (188.733 mM trolox/mg) are quite remarkable in 2,2?-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid analysis according to butylated hydroxyanisole (52.63 mM trolox/mg).Publication Metadata only Sars-cov-2 omicron varyantinin spi̇ke protei̇ni̇ne karşı doğal kumari̇nleri̇n taranması: in silico bi̇r hesaplama yaklaşımı(2022-02-27) ÖZDEMİR, MÜCAHİT; YALÇIN, BAHATTİN; Özdemir M., Yalçın B., Öztürkkan F. E., Akbaba G. B., Sertçelik M., Necefoğlu H.In this study, the interactions of coumarin derivatives with the spike protein of the coronavirus Omicron variant were investigated with the help of Molecular Docking studies. When the substrate effects of the compounds against the SARS-CoV-2 Omicron variant Spike protein are examined in silico, it has been determined that the compounds exhibit moderate antagonistic effect. There are some interactions such as hydrogen bonding, carbon-hydrogen bonding, π-π stacking, π-anion, π cation, π-alkyl and alkyl interactions between coumarin derivatives and against Omicron variant’s spike protein of Sars-CoV-2.Publication Metadata only 1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties(ELSEVIER SCIENCE SA, 2020) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Abliatipova, Aziza; Benian, Sueda; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, the preparation of two novel phthalonitrile compounds, 7-(propargyloxy)-3-(3,4-dicyanophenoxyphenyl)coumarin (1), and 7-(propargyloxy)-3-(2,3-dicyanophenoxy-phenyl)coumarin (2) were performed. Two new coumarinyl-1,2,3-triazole hybrids, (1-phenethy1-1H41,2,A-triazole 4 yl) 7 methyleneoxy 3 [F. (3,4 dicya nophenoxy)phenyl]-coumarin (3), and (1-phenethy1-1H-[1,2,3]-triazole 4 yl) 7 methyleneoxy 3 [F. (2,3 dicya nophenoxy)phenyl]-coumarin (4), were synthesized by the copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of 2-(azidoethyl)benzene with terminal ethynyl bearing coumarin derivatives (1 or 2). These novel phthalonitrile derivatives (3 and 4) were converted into their peripheral (5-7) and non-peripheral (8-10) metal-free, zinc(II) and magnesium(II) phthalocyanine counterparts. The synthesized phthalocyanine derivatives are first examples on the phthalocyanine-coumarin derivatives bearing triazole ring. The structures of all these novel compounds were characterized by variety of spectroscopic techniques including FT-IR, UV-vis, H-1 NMR, MALDI-TOF MS and elemental analysis. The photophysicochemical properties of all studied Pcs (5-10) were determined in dimethyl sulfoxide. The zinc(II) and magnesium(II) phthalocyanines bearing triazole containing coumarin substituents appear to be useful as Type II photosensitizers because the singlet oxygen quantum yields ranged in acceptable values from 0.17 to 0.49 confirmed that these phthalocyanines can be suggested as photosensitizers in Photodynamic Therapy applications. Geometry optimization, frequency analysis and molecular orbital energy values of coumarin/triazole substituted phthalocyanine were performed in Density Functional Theory method using the B3LYP/LANL2DZ level of theory.Publication Metadata only LC-ESI-tandem MS and in silico ADMET analysis of polyphenols from Rhus coriaria L. and Micromeria fruticosa (L.) Druce ssp. brachycalyx P. H. Davis(SPRINGER, 2021) YALÇIN, BAHATTİN; Taskin, Duygu; Ozdemir, Mucahit; Yalcin, BahattinBackground: Micromeria fruticosa (L.) Druce ssp. brachycalyx P. H. Davis and Rhus coriaria L., which are Lamiaceae species, are used both as spices in food and medicinally. Lamiaceae species are known to contain high amounts of polyphenols. In this study, liquid chromatography-quadrupole time-of-flight-tandem mass spectrometry (LC-QTOF-MS/MS) was used for analysis of polyphenols in the plants. Under gradient elution with using 0.1% aqueous acetic acid solution and acetonitrile mobile phases, an Agilent Poroshell C18 reversed phase column was used for the simultaneous determination of 18 polyphenols, and separation was performed in 30 min. Pharmacokinetic properties of these polyphenols such as drug-like and toxicity were estimated using open-source software, pkCSM and SwissADME. Results: These compounds were determined to represent different classes of polyphenols, including phenolic acids, flavonoids, coumarin and tannins. ADMET predictions of polyphenols indicated that these compounds are easily absorbed and do not have toxic effects. Conclusion: While the Rhus coriaria L. includes anthocyanidins, tannins, phenolic acid and flavonoids, the Micromeria fruticosa (L.) Druce ssp. brachycalyx P. H. Davis has phenolic acid, coumarin and flavonoids, according to these results. In silico ADME/Tox predictions revealed that these bioactive components are to be drug-like and non-mutagenic. These data are supportive for future analysis that can lead to their therapeutic use of the plants, suggesting that this species may be used as a natural medicinal source in the future after detailed analysis tests.Publication Metadata only Synthesis and characterization of novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted metallo phthalocyanines and investigation of their photophysical and photochemical properties(ROYAL SOC CHEMISTRY, 2019) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Karapinar, Begumhan; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, MustafaIn this study, the synthesis of novel 7-hydroxy-3-ethyl-6-hexyl-4-methylcoumarin (1), four respective phthalonitriles; 4-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (2), 3-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (3), 4-chloro-5-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (4), and 4,5-bis(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin)phthalonitrile (5) and their corresponding alpha tetra, beta tetra and beta octa 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin and beta octa 4-chloro-5-(7-oxy-3-ethyl-6-hexyl-4-methylcoumarin) substituted Zn(ii) (6a-9a) and In(iii) Cl (6b-9b) phthalocyanines has been performed. The novel purified compounds were characterized by standard characterization techniques such as elemental analysis, thermal analysis, FT-IR, UV-vis, H-1-NMR and MALDI-TOF mass spectrometry. All of the obtained phthalocyanines showed lipophilic behaviour with excellent solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine and ethyl acetate. The fluorescence quenching behaviour was investigated using 1,4-benzoquinone and potassium iodide as quenchers. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of these novel phthalocyanines (6a-9a and 6b-9b) were studied in DMF. They produced high singlet oxygen (for example phi(Delta) = 0.99 for 7b) and showed appropriate photodegradation (in the order of 10(-5)) which is very important for photodynamic therapy (PDT), and thus these phthalocyanines can be used as Type II photosensitizers in PDT applications.Publication Metadata only Anticancer effect of phthalocyanine derivatives on colorectal cancer: in vitro and in vivo model(2022-08-28) ÖZDEMİR, MÜCAHİT; YALÇIN, BAHATTİN; GÜLER E. M., ÖZDEMİR M., YALÇIN B., KOÇYİĞİT A.Colorectal cancer (CRC), also known as bowel cancer, colon cancer, or rectal cancer, develops cancer from the colon or rectum. Although 5-Fluorouracil (5-FU) is the primary antineoplastic used in treatment, its low treatment efficiency has led to the search for new agents. Phthalocyanines are aromatic macrocycles that contain four iso-indoline units connected by four nitrogen atoms. Phthalocyanines Derivatives (PD) gradually started to gain importance as anticancer agents. Our study aims to investigate the in vitro and in vivo anticancer effects of PD and 5-FU combinations on CRC. Cytotoxicity, genotoxicity, apoptosis, i-ROS, glutathione, calcium, and mitochondrial membrane potential were measured in LoVo and CCD18Co cells. Cells were given to nude mice by the xenograft method. After four weeks of single and combination therapy, tumor size was measured by in vivo imaging system (IVIS) and caliper. It was examined biochemically and histopathologically in related serum, tissues, and tumors. Combination treatment in vitro dose-dependently increased cytotoxicity, iROS, genotoxicity, apoptosis, and calcium significantly compared to a single treatment (p<0.001). DNA damage and apoptosis were induced higher in combined treatment than single treatment and increased statistically significantly (p<0.001). It was found that it decreased glutathione and MMP levels statistically (p<0.01; p<0.001). In all results of in vitro studies, PD affected cancer cells more than healthy cells. Combination treatment in vivo was found to reduce tumor size and density by a minimum of 66% at 30 days compared to a single treatment. Our results showed that PD has different anticancer properties in vivo and in vitro. The combined use of PD and 5-FU may be an option for routine colorectal cancer treatment.Publication Metadata only Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc(ii) phthalocyanines(ROYAL SOC CHEMISTRY, 2021) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Artuc, Gamze Ozgul; Akkurt, Barbaros; Yalcin, Bahattin; Satan, Umit; Durmus, Mahmut; Bulut, MustafaIn this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the presence of zinc acetate to yield 2,9(10),16(17),23(24)-tetrakis[2-phenoxy-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid] substituted zinc(ii) phthalocyanine. Some thiols, namely n-butanethiol (R-1), n-hexanethiol (R-2), 3-sulfanylpropionic acid (R-3), and 7-sulfanyl-2H-1-benzopyran-2-one (R-4), were reacted with this zinc(ii) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study.Publication Metadata only Synthesis, spectroscopic characterization, crystal structure, density functional theory studies and biological properties of coordination complex Ni(II) 2-fluorobenzoate with 3-hydroxypyridine(WILEY, 2020) YALÇIN, BAHATTİN; Sertcelik, Mustafa; Ozbek, Fureya Elif; Taslimi, Parham; Durman, Murat; Ozdemir, Mucahit; Yalcin, Bahattin; Necefoglu, Hacali; Hokelek, TuncerA novel Ni(II) complex containing 2-fluorobenzoate and 3-hydroxypyridine ligands was synthesized and characterized using elemental analysis, Fourier transform infrared (FT-IR) spectroscopy and single-crystal X-ray diffraction. FT-IR peaks show that the carboxylate group from 2-fluorobenzoate has a monodentate coordination mode. The coordination environment around the Ni2+ ion is of distorted octahedral geometry. The octahedral geometry consists of a total of four oxygen atoms from two carboxylate groups of two fluorobenzoate anions, two water molecules and two nitrogen atoms from two 3-hydroxypyridine ligands. The complex shows excellent inhibitory effects against some metabolic enzymes. K-i values for the complex were found as 108.17 +/- 25.63, 124.88 +/- 36.20, 28.11 +/- 2.87, 20.95 +/- 5.65 and 32.63 +/- 9.67 mu M against human carbonic anhydrase I, human carbonic anhydrase II, alpha-glycosidase, acetylcholinesterase and butyrylcholinesterase, respectively. In addition, geometry optimization and vibration frequencies were calculated, and single point energy was studied based on optimization. Experimental and theoretical data were compared. The B3LYP/6-31G(d,p) basis set was used for all calculations.Publication Metadata only Synthesis and photovoltaic properties of novel ferrocene-substituted metallophthalocyanines(ROYAL SOC CHEMISTRY) YALÇIN, BAHATTİN; ozdemir, Mucahit; Koksoy, Baybars; Kuruca, Halid; Altindal, Ahmet; Durmus, Mahmut; Koyuncu, Sermet; Yalcin, Bahattin; Bulut, MustafaIn this paper, a series of new metallophthalocyanines, including ferrocene groups, were designed, synthesized and, characterized, and their photovoltaic properties were investigated as alternative electron-donor materials in bulk heterojunction (BHJ) solar cells. These products were synthesized by a Sonogashira cross-coupling reaction between tetraiodophthalocyanine and ethynyl ferrocene. The newly synthesized phthalocyanines (4-6) were characterized by FT-IR, UV-Vis, H-1 NMR, and MALDI-TOF spectroscopic methods and elemental analysis. The electrochemical characterizations were carried out by cyclic voltammetry as well as differential pulse voltammetry. Density functional theory calculations were realized to prove the charge separation between ferrocene as an electron-donor and the phthalocyanine ring as an acceptor. According to UV-Vis measurements, a 25 nm red-shift was observed for complex 4 compared with complexes 5 and 6. Finally, the photovoltaic performance of these compounds used as an electron-donor moiety in a BHJ device were investigated. A function of different blend ratios was tested by fabricating a series of BHJ devices with the architecture of FTO/PEDOT:PSS/4-6: PCBM blend/Ag with an identical thickness of the active layer. The results indicated that the photovoltaic conversion efficiency of BHJ devices exhibited a strong blend-ratio dependence. The maximum power conversion efficiency was obtained by 5-based devices, as 3.65%, with a blend ratio of 1.5 : 1.0 under standard AM 1.5 illumination.