Sawsan A. Fouad, S. Hessein, S. Abbas, A. Farrag, Y. Ammar
In an attempt for development of new antimicrobial agents; new series of chromen-2-one, pyrano[3,4-c]chromene and pyridino[3,4c]chromene derivatives bearing a diazo moiety were synthesized. Chromen-2-one derivatives were synthesized via treatment of 5-(aryldiazo) salicylaldehyde with different type of active methylene derivatives. Pyrano[3,4-c]chromene and pyridino[3,4-c]chromene derivatives were synthesized via treatment of chromen-2-one derivatives with another active methylene derivatives. The synthesized compounds were evaluated for their expected antimicrobial activity; where, the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi.
{"title":"Synthesis of Chromen-2-one, Pyrano[3,4-c]chromene and Pyridino[3,4-c]chromene Derivatives as Potent Antimicrobial Agents","authors":"Sawsan A. Fouad, S. Hessein, S. Abbas, A. Farrag, Y. Ammar","doi":"10.5562/CCA3266","DOIUrl":"https://doi.org/10.5562/CCA3266","url":null,"abstract":"In an attempt for development of new antimicrobial agents; new series of chromen-2-one, pyrano[3,4-c]chromene and pyridino[3,4c]chromene derivatives bearing a diazo moiety were synthesized. Chromen-2-one derivatives were synthesized via treatment of 5-(aryldiazo) salicylaldehyde with different type of active methylene derivatives. Pyrano[3,4-c]chromene and pyridino[3,4-c]chromene derivatives were synthesized via treatment of chromen-2-one derivatives with another active methylene derivatives. The synthesized compounds were evaluated for their expected antimicrobial activity; where, the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"91 1","pages":"99-107"},"PeriodicalIF":0.3,"publicationDate":"2018-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.5562/CCA3266","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41390849","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In this study, it was shown that the chemical composition of the essential oil obtained from bitter orange peel (Aurantii amari flavedo, Citrus aurantium L., from Croatia) depends on the method of isolation. The peel essential oil was obtained by hydrodistillation and cold press method, and their chemical compositions were analyzed by gas chromatography-mass spectrometry (GC-MS). Twenty two components were characterized by mass spectra and linear retention indices. Limonene was found as dominant compound in both hydrodistillation and cold press essential oil with 91.1 % and 51.3 %, respectively. When comparing the chemical composition of two oils, a significant difference in percentage composition of three major compounds, limonene, linalool and hexadecanoic acid was observed. The antioxidant activity of the oils was tested using 2,2-diphenyl-1-picrylhydrazyl radical scavenging method (DPPH). Both oils showed very poor antioxidant activity.
{"title":"Chemical Composition and Antioxidant Activity of Essential Oil Obtained from Bitter Orange Peel (Citrus aurantium L.) Using Two Methods","authors":"Mila Radan, Antonija Parčina, F. Burčul","doi":"10.5562/CCA3294","DOIUrl":"https://doi.org/10.5562/CCA3294","url":null,"abstract":"In this study, it was shown that the chemical composition of the essential oil obtained from bitter orange peel (Aurantii amari flavedo, Citrus aurantium L., from Croatia) depends on the method of isolation. The peel essential oil was obtained by hydrodistillation and cold press method, and their chemical compositions were analyzed by gas chromatography-mass spectrometry (GC-MS). Twenty two components were characterized by mass spectra and linear retention indices. Limonene was found as dominant compound in both hydrodistillation and cold press essential oil with 91.1 % and 51.3 %, respectively. When comparing the chemical composition of two oils, a significant difference in percentage composition of three major compounds, limonene, linalool and hexadecanoic acid was observed. The antioxidant activity of the oils was tested using 2,2-diphenyl-1-picrylhydrazyl radical scavenging method (DPPH). Both oils showed very poor antioxidant activity.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"91 1","pages":"125-128"},"PeriodicalIF":0.3,"publicationDate":"2018-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45477565","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stanimir Vuk-Pavlović, Bojan Benko, Vesna Svetličić
SV-P: Kao učenici iz njegova znanstvenog razdoblja u biofizici tvrdimo, možda sebično, da je upravo tada dr. Maričić ostavio najvažniji trag. Izvjesno je da je njegov najvažniji doprinos našoj znanosti upravo onaj koji je trajao najkraće: njegov pionirski doprinos razvoju biofizike, biofizičkog obrazovanja i kvantitativnog pristupa biološkim problemima. Bio nam je učiteljem u svoj punini tih pojmova, a na nas je utjecao i svojom osobnošću. Zato nam nije cilj ovdje nabrajati niti raščlanjivati mnogobojne doprinose dr. Maričića kemijskoj tehnologiji nakon II. svjetskog rata, potom njegovo predvodništvo u biofizici i, na koncu, u znanosti o znanosti[1–4], već podijelimo radije osobne uspomene na nj.
SV-P：作为一名生物物理科学时代的科学家，我们声称，也许是自私的，Maričic博士刚刚留下了最重要的痕迹。他对我们的科学最重要的贡献是对一个持续时间很短的贡献：他对发展生物物理、生物物理教育和定量获取生物问题的先驱贡献。他是我们充满这些思想的老师，他的个性也影响着我们。因此，我们在这里的目标不是起草或解释二战后对Maričic博士化学技术的许多贡献。svjetskog rata，potom njegovo predvdništvo u biofizici i，na koncu，u znanosti o znanosti[1-4]，većpodijelimo radije osobne uspomene na nj。
{"title":"Učenici se sjećaju Siniše Maričića (1926.–2017.): Uspravan do kraja","authors":"Stanimir Vuk-Pavlović, Bojan Benko, Vesna Svetličić","doi":"10.5562/CCA3358HR","DOIUrl":"https://doi.org/10.5562/CCA3358HR","url":null,"abstract":"SV-P: Kao učenici iz njegova znanstvenog razdoblja u biofizici tvrdimo, možda sebično, da je upravo tada dr. Maričić ostavio najvažniji trag. Izvjesno je da je njegov najvažniji doprinos našoj znanosti upravo onaj koji je trajao najkraće: njegov pionirski doprinos razvoju biofizike, biofizičkog obrazovanja i kvantitativnog pristupa biološkim problemima. Bio nam je učiteljem u svoj punini tih pojmova, a na nas je utjecao i svojom osobnošću. Zato nam nije cilj ovdje nabrajati niti raščlanjivati mnogobojne doprinose dr. Maričića kemijskoj tehnologiji nakon II. svjetskog rata, potom njegovo predvodništvo u biofizici i, na koncu, u znanosti o znanosti[1–4], već podijelimo radije osobne uspomene na nj.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"91 1","pages":"133-135"},"PeriodicalIF":0.3,"publicationDate":"2018-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41955693","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sobhi M. Gomha, Zeinab A. Muhammad, Hassan M. Abdel‐aziz, E. E. El-Arab
A new series of morpholinyl-chalcones 2a–d was prepared by reaction of 2-oxo-N,4-diarylbut-3-enehydrazonoyl chlorides 1a–d with morpholine. These chalcones were used as a building block for constructing pyrazoles 3a–d and 3,4-dihydropyrimidine-2(1H)-thione 6 via their reaction with phenylhydrazine and thiourea, respectively. Moreover, a new series of azolopyrimidine derivatives 11a,b, 15, 17, 19, and 21 incorporating morpholine moiety were synthesized by reaction of 1-morpholino-4-phenyl-1-(2-phenylhydrazono)but-3-en-2-one (2a) with a number of heterocyclic amines in the presence of a catalytic amount of acetic acid. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. All the synthesized compounds were tested for in vitro activities against two antitumor cell lines, human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 6, 8c and 17 have promising activities compared with cisplatin.
{"title":"Synthesis of New Azoles and Azolopyrimidines Incorporating Morpholine Moiety as Potent Anti-Tumor Agents","authors":"Sobhi M. Gomha, Zeinab A. Muhammad, Hassan M. Abdel‐aziz, E. E. El-Arab","doi":"10.5562/CCA3279","DOIUrl":"https://doi.org/10.5562/CCA3279","url":null,"abstract":"A new series of morpholinyl-chalcones 2a–d was prepared by reaction of 2-oxo-N,4-diarylbut-3-enehydrazonoyl chlorides 1a–d with morpholine. These chalcones were used as a building block for constructing pyrazoles 3a–d and 3,4-dihydropyrimidine-2(1H)-thione 6 via their reaction with phenylhydrazine and thiourea, respectively. Moreover, a new series of azolopyrimidine derivatives 11a,b, 15, 17, 19, and 21 incorporating morpholine moiety were synthesized by reaction of 1-morpholino-4-phenyl-1-(2-phenylhydrazono)but-3-en-2-one (2a) with a number of heterocyclic amines in the presence of a catalytic amount of acetic acid. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. All the synthesized compounds were tested for in vitro activities against two antitumor cell lines, human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 6, 8c and 17 have promising activities compared with cisplatin.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"91 1","pages":"43-51"},"PeriodicalIF":0.3,"publicationDate":"2018-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.5562/CCA3279","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47351611","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Juraj Nikolić, A. Šantić, L. Pavić, D. Pajić, P. Mošner, L. Koudelka, A. Milanković
Electrical transport in mixed ion-polaron glasses has been investigated in four series of glasses containing transition metal oxides (TMO) namely WO3/MoO3, and Na+/Ag+ ions with the composition xWO3- (30-0.5x)Na2O-(30-0.5x)ZnO-40P2O5, xWO3-(30- 0.5x)Ag2O-(30-0.5x)ZnO-40P2O5, xMoO3-(30-0.5x)Na2O- (30-0.5x)ZnO-40P2O5, and xMoO3-(30-0.5x)Ag2O-(30- 0.5x)ZnO-40P2O5, 0 ≤ x ≤ 60 (mol%). The DC conductivity of Na-glasses up to 30 mol% of WO3 and MoO3 is almost identical due to the dominance of ionic conductivity. In this compositional region, the introduction of tungstate and molybdate units increases the mobility of sodium ions and compensates the decrease in sodium number density. On the other hand, with increasing WO3 and MoO3 content and decreasing Ag+ ion concentration in Ag-glasses the DC conductivity decreases for few orders of magnitude. A significant difference in conductivity is observed for glasses with higher WO3 and MoO3 content. While for glasses containing WO3 the conductivity rapidly increases due to a huge polaronic contribution indicating a turnover from predominantly ionic to polaronic transport, the conductivity for MoO3- glasses decreases in the entire mixed compositional range suggesting dominant ionic transport. The changes in the conduction mechanism with the systematic alternation of the glass composition have been analyzed in correlation with the structural modifications and variations of molybdenum and tungsten in different oxidation states.
{"title":"Mixed Ion-Polaron Glasses as New Cathode Materials","authors":"Juraj Nikolić, A. Šantić, L. Pavić, D. Pajić, P. Mošner, L. Koudelka, A. Milanković","doi":"10.5562/CCA3330","DOIUrl":"https://doi.org/10.5562/CCA3330","url":null,"abstract":"Electrical transport in mixed ion-polaron glasses has been investigated in four series of glasses containing transition metal oxides (TMO) namely WO3/MoO3, and Na+/Ag+ ions with the composition xWO3- (30-0.5x)Na2O-(30-0.5x)ZnO-40P2O5, xWO3-(30- 0.5x)Ag2O-(30-0.5x)ZnO-40P2O5, xMoO3-(30-0.5x)Na2O- (30-0.5x)ZnO-40P2O5, and xMoO3-(30-0.5x)Ag2O-(30- 0.5x)ZnO-40P2O5, 0 ≤ x ≤ 60 (mol%). The DC conductivity of Na-glasses up to 30 mol% of WO3 and MoO3 is almost identical due to the dominance of ionic conductivity. In this compositional region, the introduction of tungstate and molybdate units increases the mobility of sodium ions and compensates the decrease in sodium number density. On the other hand, with increasing WO3 and MoO3 content and decreasing Ag+ ion concentration in Ag-glasses the DC conductivity decreases for few orders of magnitude. A significant difference in conductivity is observed for glasses with higher WO3 and MoO3 content. While for glasses containing WO3 the conductivity rapidly increases due to a huge polaronic contribution indicating a turnover from predominantly ionic to polaronic transport, the conductivity for MoO3- glasses decreases in the entire mixed compositional range suggesting dominant ionic transport. The changes in the conduction mechanism with the systematic alternation of the glass composition have been analyzed in correlation with the structural modifications and variations of molybdenum and tungsten in different oxidation states.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"657-665"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.5562/CCA3330","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44127980","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Bakić, K. Leko, N. Cindro, T. Portada, T. Hrenar, Leo Frkanec, Gordan Horvat, J. Požar, V. Tomišić
Two novel fluorescent calix[4]arenes comprising diphenylanthracene moiety at the lower rim were synthetized and their complexation with alkali metal cations in acetonitrile/dichloromethane and methanol/dichloromethane mixtures (φ = 0.5) was studied experimentally and by classical molecular dynamics and quantum chemical calculations. The monosubstituted calixarene derivative (L1) proved to be a poor cation receptor, whereas the ester-based macrocycle (L2) exhibited rather high affinity towards lithium, sodium and potassium cations, particularly in MeCN/CH2Cl2. All complexation reactions were enthalpically controlled, whereby the overall stability was the largest in the case of sodium complex. The computational investigations provided an additional insight into the complexation properties and structures of complex species. The molecular dynamics simulations indicated the occurrence of inclusion of solvent molecules in the calixarene hydrophobic cavity of the free and complexed ligand, which was found to significantly affect the complexation equilibria.
{"title":"Synthesis of Fluorescent Diphenylanthracene-Based Calix[4]arene Derivatives and their Complexation with Alkali Metal Cations","authors":"M. Bakić, K. Leko, N. Cindro, T. Portada, T. Hrenar, Leo Frkanec, Gordan Horvat, J. Požar, V. Tomišić","doi":"10.5562/CCA3308","DOIUrl":"https://doi.org/10.5562/CCA3308","url":null,"abstract":"Two novel fluorescent calix[4]arenes comprising diphenylanthracene moiety at the lower rim were synthetized and their complexation with alkali metal cations in acetonitrile/dichloromethane and methanol/dichloromethane mixtures (φ = 0.5) was studied experimentally and by classical molecular dynamics and quantum chemical calculations. The monosubstituted calixarene derivative (L1) proved to be a poor cation receptor, whereas the ester-based macrocycle (L2) exhibited rather high affinity towards lithium, sodium and potassium cations, particularly in MeCN/CH2Cl2. All complexation reactions were enthalpically controlled, whereby the overall stability was the largest in the case of sodium complex. The computational investigations provided an additional insight into the complexation properties and structures of complex species. The molecular dynamics simulations indicated the occurrence of inclusion of solvent molecules in the calixarene hydrophobic cavity of the free and complexed ligand, which was found to significantly affect the complexation equilibria.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"711-725"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43737025","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Effect of Methoxy Substitution on Supramolecular Arrangement of Borondifluorides of 2'-Hydroxy Chalcones and their Solid-State NIR Fluorescence","authors":"A. D'Aléo, E. Zaborova, F. Fages","doi":"10.5562/CCA3241","DOIUrl":"https://doi.org/10.5562/CCA3241","url":null,"abstract":"","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"583-588"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45997668","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Marija Alešković, M. Glavaš, Marina Šekutor, K. Mlinarić-Majerski
Two new adamantane anion receptors with amidopyrrole side arms were prepared and their anion binding ability in DMSO solutions with TBA salts (Cl–, AcO– and H2PO4–) was investigated by UV/Vis spectroscopy. After calculating the corresponding association constants of receptor-anion complexes, it became apparent that only one amidopyrrole side arm was engaged in complexation. These experimental findings were rationalized using computational tools and the binding mode was proposed. In addition to the found 1 : 1 stoichiometry, we showed that the studied receptors bind oxo-anions (H2PO4– and AcO–) more strongly than spherical halogenide (Cl–) anions.
{"title":"Synthesis and Anion Binding Assessment of Novel Adamantane Amidopyrroles","authors":"Marija Alešković, M. Glavaš, Marina Šekutor, K. Mlinarić-Majerski","doi":"10.5562/CCA3248","DOIUrl":"https://doi.org/10.5562/CCA3248","url":null,"abstract":"Two new adamantane anion receptors with amidopyrrole side arms were prepared and their anion binding ability in DMSO solutions with TBA salts (Cl–, AcO– and H2PO4–) was investigated by UV/Vis spectroscopy. After calculating the corresponding association constants of receptor-anion complexes, it became apparent that only one amidopyrrole side arm was engaged in complexation. These experimental findings were rationalized using computational tools and the binding mode was proposed. In addition to the found 1 : 1 stoichiometry, we showed that the studied receptors bind oxo-anions (H2PO4– and AcO–) more strongly than spherical halogenide (Cl–) anions.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"637-643"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44324764","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This paper describes the synthesis of an amide based conjugate of ferrocene (Fc), ethylenediamine (eda) and iminodiacetamide (imda), Fc-eda-imda (2). The compound (2) is characterized by various spectroscopic, crystallographic and thermoanalytical techniques in solid state and in solution. By crystallization of the title compound 2 from methanol or chloroform, two different crystalline forms 2a and 2b were obtained, respectively. In their X-ray single crystal structures, 2a and 2b reveal similar 2D hydrogen bonding networks, but differ by supramolecular organization, namely aromatic π – π stacking interactions in the third spatial dimension.
{"title":"A Case Study of Supramolecular Organization: One Ferrocene Substituted Iminodiacetamide and its Chloroform Solvate","authors":"N. P. Juraj, J. Pennec, B. Perić, S. Kirin","doi":"10.5562/CCA3270","DOIUrl":"https://doi.org/10.5562/CCA3270","url":null,"abstract":"This paper describes the synthesis of an amide based conjugate of ferrocene (Fc), ethylenediamine (eda) and iminodiacetamide (imda), Fc-eda-imda (2). The compound (2) is characterized by various spectroscopic, crystallographic and thermoanalytical techniques in solid state and in solution. By crystallization of the title compound 2 from methanol or chloroform, two different crystalline forms 2a and 2b were obtained, respectively. In their X-ray single crystal structures, 2a and 2b reveal similar 2D hydrogen bonding networks, but differ by supramolecular organization, namely aromatic π – π stacking interactions in the third spatial dimension.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"613-623"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46228635","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Iva Orehovec, D. Glavač, I. Dokli, M. Gredičak, I. Piantanida
Two novel pyrene – quinoline conjugates differing in the linker flexibility between aryls were prepared. In comparison with referent pyrene derivative, both conjugates showed intramolecular pyrene – quinoline stacking in aqueous medium, much more efficient for rigid conjugate. Consequently, only rigid conjugate showed excimer fluorescence with exceptionally strong bathochromic shift (+ 55 nm) of emission maximum in respect to referent pyrene analogue and flexible conjugate. All studied compounds showed similar, 10 μmol dm−3 affinity toward ds – DNA, characterised in general by fluorescence quenching. The flexible conjugate showed at large excess of DNA over dye formation of pyrene – quinoline excimer, while rigid conjugate retained excimer emission throughout all DNA concentrations. Lack of significant thermal stabilisation of ds – DNA by studied compounds and minor changes in CD spectrum of DNA supported non – specific agglomeration of both conjugates and referent pyrene analogue within hydrophobic DNA grooves as the dominant binding mode.
{"title":"Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA","authors":"Iva Orehovec, D. Glavač, I. Dokli, M. Gredičak, I. Piantanida","doi":"10.5562/CCA3269","DOIUrl":"https://doi.org/10.5562/CCA3269","url":null,"abstract":"Two novel pyrene – quinoline conjugates differing in the linker flexibility between aryls were prepared. In comparison with referent pyrene derivative, both conjugates showed intramolecular pyrene – quinoline stacking in aqueous medium, much more efficient for rigid conjugate. Consequently, only rigid conjugate showed excimer fluorescence with exceptionally strong bathochromic shift (+ 55 nm) of emission maximum in respect to referent pyrene analogue and flexible conjugate. All studied compounds showed similar, 10 μmol dm−3 affinity toward ds – DNA, characterised in general by fluorescence quenching. The flexible conjugate showed at large excess of DNA over dye formation of pyrene – quinoline excimer, while rigid conjugate retained excimer emission throughout all DNA concentrations. Lack of significant thermal stabilisation of ds – DNA by studied compounds and minor changes in CD spectrum of DNA supported non – specific agglomeration of both conjugates and referent pyrene analogue within hydrophobic DNA grooves as the dominant binding mode.","PeriodicalId":10822,"journal":{"name":"Croatica Chemica Acta","volume":"90 1","pages":"603-611"},"PeriodicalIF":0.3,"publicationDate":"2017-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.5562/CCA3269","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44570423","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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