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Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application

Yıl 2020, Cilt: 10 Sayı: 3, 1767 - 1778, 01.09.2020
https://doi.org/10.21597/jist.679021

Öz

A series of facile optical probe has been easily developed by a one-step Schiff base type reaction of 2,4-dihydroxybenzaldehyde and ortho, meta or para aminophenol. Schiff base compounds as fluorescence sensor were utilized to identify metal ions by spectrophotometric techniques. The data of absorption and emission spectra displayed the extraordinary selective and sensitive sensor properties for Schiff base probe derived from ortho aminophenol (SB-2) toward Al3+ ions. Upon introducing Al3+ ions, an excellent increase in the fluorescence intensity of the probe (SB-2) resulting in color change was observed because of blocking the photoinduced electron transfer (PET) mechanism of azomethine unit. The specific bonding mode of probe (SB-2) with Al3+ was verified by using a series of spectroscopic techniques such as FT-IR, 1H NMR, and UV-vis (Job-plot data). The detection limit of probe (SB-2) toward Al3+was determined around 10−7M. Furthermore, cell imaging studies of probe (SB-2) were also performed and from these experiments, it was seen that the presence of even trace amounts of Al3+ in living cells could be noticeably detected by (SB-2). In this study, antimicrobial properties of Schiff base compounds were also carried out towards some selected bacteria species. This presented work provides a method for design, facile synthesis and application of effective fluorescence probes toward Al3+ ions in biological systems.

Kaynakça

  • Altschuler E, 1999. Aluminum-containing antacids as a cause of idiopathic Parkinson's disease. MedicalHypotheses 53(1):22-23.
  • Baxter NJ, Blackburn GM, Marston JP, Hounslow AM, Cliff MJ, Bermel W, Williams NH, Hollfelder F, Wemmer DE, Waltho JP, 2008. Anionic charge is prioritized over geometry in aluminum and magnesium fluoride transition state analogs of phosphoryl transfer enzymes. Journal of American Chemical Society 130: 3952-3958.
  • Benesi HA, Hildebrand JH, 1949. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of American Chemical Society 71(8):2703–2707.
  • Cicekbilek F., Yilmaz B., Bayrakci M., Gezici O, 2019. An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent. Journal of Fluorescence 29:1349–1358.
  • Dilleen JW, Birch BJ, Haggett BGD, 1999. Electrochemical detection of aluminium using single-use sensors. Analytical Communications 36:363-365.
  • Ding WH, Wang D, Zheng XJ, Ding WJ, Zheng JQ, Mu WH, Cao W, Jin LP, 2015. A turn-on fluorescence chemosensor for Al3+, F− and CN− ions, and its application in cell imaging. Sensors and Actuators B: Chemical209:359-367.
  • Fiebelkorn KR, Crawford SA, McElmeel ML, Jorgensen JH, 2003. Practical disk diffusion method for detection of inducible clindamycin resistance in Staphylococcus aureus and coagulase-negative staphylococci. Journal of Clinical Microbiology41(10):4740-4744.
  • Gupta VK, Ganjali MR, Norouzi P, Khani H, Nayak A, Agarwal S, 2011. Electro-chemical analysis of some toxic metals by ion selective electrodes. Critical Reviews in Analytical Chemistry 41(4):282–313.
  • Gupta VK, Shoora SK, Kumawat LK, Jain AK, 2015. A highly selective colorimetric and turn-on fluorescent chemosensor based on 1-(2-pyridylazo)-2-naphthol for the detection of aluminium(III) ions. Sensors and Actuators B: Chemicals 209:15–24.
  • Gupta VK, Mergu N, Kumawat LK,Singh AK, 2015. A reversible fluorescence “off–on–off” sensor for sequential detection of aluminum and acetate/fluoride ions. Talanta 144(1):80-89.
  • Gupta SD., Revathi B., Mazaira GI., Galigniana MD., Subrahmanyam CVS., Gowrishankar NL., Raghavendra NM, 2015. 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead. Bioorganic Chemistry 59: 97-105.
  • Janakipriya S, Chereddy NR, Korrapati P, Thennarasu S, Mandal AB, 2016. Selective interactions of trivalent cations Fe3+, Al3+ and Cr3+ turn on fluorescence in a naphthalimide based single molecular probe. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 153:465–470.
  • Jeyanthi D, Iniya M,Krishnaveni K,Chellppa D, 2013. A ratiometric fluorescentsensor for selective recognition of Al3+ ions based on a simple benzimidazole platform, RSC Advances 3:20984–20989.
  • Job P, 1928. Formation and stability of ınorganic complexes in solution. Annales de Chimie 9:113–203.
  • Keskin S, Bayrakci M, 2019. A simple and highly sensitive turn-onschiff base type naked-eye fluorescent sensorfor aluminum ion in living cells. Acta Chimica Slovenica 66(4):792–801.
  • Kim HM, Jung C, Kim BR, Jung SY, Hong JH, Ko YG, Lee KJ, Cho BR, 2007. Environment-sensitive two-photon probe for intracellular free magnesium ions in live tissue. Angewandte Chemie 46:3460 –3463.
  • Kim S, Noh JY, Kim KY, Kim JH, Kang HK,Nam SW, Kim SH, Park S, Kim C, Kim J, 2012. Salicylimine-based fluorescent chemosensor for aluminum ions and application to bioimaging. Journal of Inorganic Chemistry 51(6):3597–3602.
  • LakowiczJR, 2002. Topics in fluorescence spectroscopy: probe design and chemical sensing; Kluwer Academic Publishers: New York, 4-11p.
  • Murtaza S., Abbas A., Iftikhar K., Shamim S., Akhtar MS., Razzaq Z., Naseem K., Elgorban AM, 2016. Synthesis, biological activities and docking studies of novel 2,4-dihydroxybenzaldehyde based Schiff base. Medicinal Chemistry Research 25: 2860–2871.
  • Neelakantan MA,Rusalraj F, Dharmaraja J, Johnsonraja S, Jeyakumar T, Sankarayana PM, 2008. Spectral characterization, cyclic voltammetry, morphology, biological activities and DNA cleaving studies of amino acid Schiff base metal(II) complexes. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, 71(4):1599-1609.
  • Santos-Figueroa LE, Moragues ME, Climent E, Agostini A, Martinez-Manez R, Sancenon F, 2013. Chromogenic and fluorogenic chemosensors and reagents for anions A comprehensive review of the years 2010–2011. Chemical Sociecty Review 42(8):3489–3613.
  • Shoora SK, Jain AK, Gupta VK, 2015. A simple Schiff base based novel optical probe for aluminium (III) ions. Sensors and Actuators B: Chemicals 216:86–104.
  • Simona T, Shellaiahb M, Srinivasadesikanc V, Lina CC, Koa FH, Sunb KW, Linc MC, 2016. A simple pyrene based AIEE active schiff base probe for selective naked eye and fluoresence off–on detection of trivalent cations with live cell application. Sens. Actuators B 231:18-29.
  • Soni MG, White SM, Flamm WG, Regul GAB, 2001. Safety evaluation of dietary aluminum. Regulatory Toxicology and Pharmacology 33(1):66-79.
  • Soroka K, Vithanage RS, Phillips DA, Walker B, Dasgupta PK,1987. Fluorescence properties of metal complexes of 8-hydroxyquinoline-5-sulfonic acid and chromatographic applications. Analytical Chemistry 59(4):629–636.
  • Sun X, Liu J, Zhuang C, Yang X, Han Y, Shao B, Song M, Li Y,Zhu Y, 2016. Aluminum trichloride induces bone impairment through TGF-β1/Smad signaling pathway. Toxicology 14:49-57.
  • Sztanke K, Maziarka A, Osinka A, Sztanke M 2013. An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorganic and Medicinal Chemistry 21:3648–3666.
  • Mozhgan T., Mohammad Y., Kheirollah M., Masoumeh T., Mahmood D.A, 2017. Synthesis, Characterization and Antimicrobial Activity of Two Novel Sulfonamide Schiff Base Compounds. Pharmaceutical Chemistry Journal 51:425–428.
  • Tian J, Yan X, Yang H, Tian F, 2015. A novel turn-on Schiff-base fluorescent sensor for aluminum(III) ions in living cells. RSC Advances 5:107012-107019.
  • Zhong Z, Zhang D, Li D, Zheng G, Tian Z, 2016. Turn-on fluorescence sensor based on naphthalene anhydride for Hg2+. Tetrahedron 72(49):8050-8074.
  • Zhou D, Sun C, Chen C, Cui X, Li X, 2015. Research of a highly selective fluorescent chemosensor for aluminum(III) ions based on photoinduced electron transfer. Journal of Molecular Structures 1079:315-320.
  • ZhuJ, Zhang Y, Wang L, Sun T, Wang M, Wang Y, Ma D, Yang Q, Tang Y, 2016. A simple turn-on Schiff base fluorescence sensor for aluminum ion Tetrahedron Letters 57: 3535–3539.
  • Walton JR, 2006. Aluminum in hippocampal neurons from humans with Alzheimer's disease. Neurotoxicology 27:385-394.
  • Wang JT, Wang HD 2011. Preparation of soluble p-aminobenzoyl chitosan ester by Schiff’s base and Antibacterial activity of the derivatives. International Journal of Biological Macromolecules 48:523–529.

Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application

Yıl 2020, Cilt: 10 Sayı: 3, 1767 - 1778, 01.09.2020
https://doi.org/10.21597/jist.679021

Öz

A series of facile optical probe has been easily developed by a one-step Schiff base type reaction of 2,4-dihydroxybenzaldehyde and ortho, meta or para aminophenol. Schiff base compounds as fluorescence sensor were utilized to identify metal ions by spectrophotometric techniques. The data of absorption and emission spectra displayed the extraordinary selective and sensitive sensor properties for Schiff base probe derived from ortho aminophenol (SB-2) toward Al3+ ions. Upon introducing Al3+ ions, an excellent increase in the fluorescence intensity of the probe (SB-2) resulting in color change was observed because of blocking the photoinduced electron transfer (PET) mechanism of azomethine unit. The specific bonding mode of probe (SB-2) with Al3+ was verified by using a series of spectroscopic techniques such as FT-IR, 1H NMR, and UV-vis (Job-plot data). The detection limit of probe (SB-2) toward Al3+was determined around 10−7M. Furthermore, cell imaging studies of probe (SB-2) were also performed and from these experiments, it was seen that the presence of even trace amounts of Al3+ in living cells could be noticeably detected by (SB-2). In this study, antimicrobial properties of Schiff base compounds were also carried out towards some selected bacteria species. This presented work provides a method for design, facile synthesis and application of effective fluorescence probes toward Al3+ ions in biological systems.

Kaynakça

  • Altschuler E, 1999. Aluminum-containing antacids as a cause of idiopathic Parkinson's disease. MedicalHypotheses 53(1):22-23.
  • Baxter NJ, Blackburn GM, Marston JP, Hounslow AM, Cliff MJ, Bermel W, Williams NH, Hollfelder F, Wemmer DE, Waltho JP, 2008. Anionic charge is prioritized over geometry in aluminum and magnesium fluoride transition state analogs of phosphoryl transfer enzymes. Journal of American Chemical Society 130: 3952-3958.
  • Benesi HA, Hildebrand JH, 1949. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of American Chemical Society 71(8):2703–2707.
  • Cicekbilek F., Yilmaz B., Bayrakci M., Gezici O, 2019. An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent. Journal of Fluorescence 29:1349–1358.
  • Dilleen JW, Birch BJ, Haggett BGD, 1999. Electrochemical detection of aluminium using single-use sensors. Analytical Communications 36:363-365.
  • Ding WH, Wang D, Zheng XJ, Ding WJ, Zheng JQ, Mu WH, Cao W, Jin LP, 2015. A turn-on fluorescence chemosensor for Al3+, F− and CN− ions, and its application in cell imaging. Sensors and Actuators B: Chemical209:359-367.
  • Fiebelkorn KR, Crawford SA, McElmeel ML, Jorgensen JH, 2003. Practical disk diffusion method for detection of inducible clindamycin resistance in Staphylococcus aureus and coagulase-negative staphylococci. Journal of Clinical Microbiology41(10):4740-4744.
  • Gupta VK, Ganjali MR, Norouzi P, Khani H, Nayak A, Agarwal S, 2011. Electro-chemical analysis of some toxic metals by ion selective electrodes. Critical Reviews in Analytical Chemistry 41(4):282–313.
  • Gupta VK, Shoora SK, Kumawat LK, Jain AK, 2015. A highly selective colorimetric and turn-on fluorescent chemosensor based on 1-(2-pyridylazo)-2-naphthol for the detection of aluminium(III) ions. Sensors and Actuators B: Chemicals 209:15–24.
  • Gupta VK, Mergu N, Kumawat LK,Singh AK, 2015. A reversible fluorescence “off–on–off” sensor for sequential detection of aluminum and acetate/fluoride ions. Talanta 144(1):80-89.
  • Gupta SD., Revathi B., Mazaira GI., Galigniana MD., Subrahmanyam CVS., Gowrishankar NL., Raghavendra NM, 2015. 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead. Bioorganic Chemistry 59: 97-105.
  • Janakipriya S, Chereddy NR, Korrapati P, Thennarasu S, Mandal AB, 2016. Selective interactions of trivalent cations Fe3+, Al3+ and Cr3+ turn on fluorescence in a naphthalimide based single molecular probe. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 153:465–470.
  • Jeyanthi D, Iniya M,Krishnaveni K,Chellppa D, 2013. A ratiometric fluorescentsensor for selective recognition of Al3+ ions based on a simple benzimidazole platform, RSC Advances 3:20984–20989.
  • Job P, 1928. Formation and stability of ınorganic complexes in solution. Annales de Chimie 9:113–203.
  • Keskin S, Bayrakci M, 2019. A simple and highly sensitive turn-onschiff base type naked-eye fluorescent sensorfor aluminum ion in living cells. Acta Chimica Slovenica 66(4):792–801.
  • Kim HM, Jung C, Kim BR, Jung SY, Hong JH, Ko YG, Lee KJ, Cho BR, 2007. Environment-sensitive two-photon probe for intracellular free magnesium ions in live tissue. Angewandte Chemie 46:3460 –3463.
  • Kim S, Noh JY, Kim KY, Kim JH, Kang HK,Nam SW, Kim SH, Park S, Kim C, Kim J, 2012. Salicylimine-based fluorescent chemosensor for aluminum ions and application to bioimaging. Journal of Inorganic Chemistry 51(6):3597–3602.
  • LakowiczJR, 2002. Topics in fluorescence spectroscopy: probe design and chemical sensing; Kluwer Academic Publishers: New York, 4-11p.
  • Murtaza S., Abbas A., Iftikhar K., Shamim S., Akhtar MS., Razzaq Z., Naseem K., Elgorban AM, 2016. Synthesis, biological activities and docking studies of novel 2,4-dihydroxybenzaldehyde based Schiff base. Medicinal Chemistry Research 25: 2860–2871.
  • Neelakantan MA,Rusalraj F, Dharmaraja J, Johnsonraja S, Jeyakumar T, Sankarayana PM, 2008. Spectral characterization, cyclic voltammetry, morphology, biological activities and DNA cleaving studies of amino acid Schiff base metal(II) complexes. Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, 71(4):1599-1609.
  • Santos-Figueroa LE, Moragues ME, Climent E, Agostini A, Martinez-Manez R, Sancenon F, 2013. Chromogenic and fluorogenic chemosensors and reagents for anions A comprehensive review of the years 2010–2011. Chemical Sociecty Review 42(8):3489–3613.
  • Shoora SK, Jain AK, Gupta VK, 2015. A simple Schiff base based novel optical probe for aluminium (III) ions. Sensors and Actuators B: Chemicals 216:86–104.
  • Simona T, Shellaiahb M, Srinivasadesikanc V, Lina CC, Koa FH, Sunb KW, Linc MC, 2016. A simple pyrene based AIEE active schiff base probe for selective naked eye and fluoresence off–on detection of trivalent cations with live cell application. Sens. Actuators B 231:18-29.
  • Soni MG, White SM, Flamm WG, Regul GAB, 2001. Safety evaluation of dietary aluminum. Regulatory Toxicology and Pharmacology 33(1):66-79.
  • Soroka K, Vithanage RS, Phillips DA, Walker B, Dasgupta PK,1987. Fluorescence properties of metal complexes of 8-hydroxyquinoline-5-sulfonic acid and chromatographic applications. Analytical Chemistry 59(4):629–636.
  • Sun X, Liu J, Zhuang C, Yang X, Han Y, Shao B, Song M, Li Y,Zhu Y, 2016. Aluminum trichloride induces bone impairment through TGF-β1/Smad signaling pathway. Toxicology 14:49-57.
  • Sztanke K, Maziarka A, Osinka A, Sztanke M 2013. An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorganic and Medicinal Chemistry 21:3648–3666.
  • Mozhgan T., Mohammad Y., Kheirollah M., Masoumeh T., Mahmood D.A, 2017. Synthesis, Characterization and Antimicrobial Activity of Two Novel Sulfonamide Schiff Base Compounds. Pharmaceutical Chemistry Journal 51:425–428.
  • Tian J, Yan X, Yang H, Tian F, 2015. A novel turn-on Schiff-base fluorescent sensor for aluminum(III) ions in living cells. RSC Advances 5:107012-107019.
  • Zhong Z, Zhang D, Li D, Zheng G, Tian Z, 2016. Turn-on fluorescence sensor based on naphthalene anhydride for Hg2+. Tetrahedron 72(49):8050-8074.
  • Zhou D, Sun C, Chen C, Cui X, Li X, 2015. Research of a highly selective fluorescent chemosensor for aluminum(III) ions based on photoinduced electron transfer. Journal of Molecular Structures 1079:315-320.
  • ZhuJ, Zhang Y, Wang L, Sun T, Wang M, Wang Y, Ma D, Yang Q, Tang Y, 2016. A simple turn-on Schiff base fluorescence sensor for aluminum ion Tetrahedron Letters 57: 3535–3539.
  • Walton JR, 2006. Aluminum in hippocampal neurons from humans with Alzheimer's disease. Neurotoxicology 27:385-394.
  • Wang JT, Wang HD 2011. Preparation of soluble p-aminobenzoyl chitosan ester by Schiff’s base and Antibacterial activity of the derivatives. International Journal of Biological Macromolecules 48:523–529.
Toplam 34 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Mevlüt Bayrakcı 0000-0002-0416-2870

Bahar Yılmaz 0000-0002-6315-3018

Yayımlanma Tarihi 1 Eylül 2020
Gönderilme Tarihi 23 Ocak 2020
Kabul Tarihi 21 Nisan 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 10 Sayı: 3

Kaynak Göster

APA Bayrakcı, M., & Yılmaz, B. (2020). Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application. Journal of the Institute of Science and Technology, 10(3), 1767-1778. https://doi.org/10.21597/jist.679021
AMA Bayrakcı M, Yılmaz B. Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application. Iğdır Üniv. Fen Bil Enst. Der. Eylül 2020;10(3):1767-1778. doi:10.21597/jist.679021
Chicago Bayrakcı, Mevlüt, ve Bahar Yılmaz. “Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base With Biological Application”. Journal of the Institute of Science and Technology 10, sy. 3 (Eylül 2020): 1767-78. https://doi.org/10.21597/jist.679021.
EndNote Bayrakcı M, Yılmaz B (01 Eylül 2020) Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application. Journal of the Institute of Science and Technology 10 3 1767–1778.
IEEE M. Bayrakcı ve B. Yılmaz, “Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application”, Iğdır Üniv. Fen Bil Enst. Der., c. 10, sy. 3, ss. 1767–1778, 2020, doi: 10.21597/jist.679021.
ISNAD Bayrakcı, Mevlüt - Yılmaz, Bahar. “Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base With Biological Application”. Journal of the Institute of Science and Technology 10/3 (Eylül 2020), 1767-1778. https://doi.org/10.21597/jist.679021.
JAMA Bayrakcı M, Yılmaz B. Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application. Iğdır Üniv. Fen Bil Enst. Der. 2020;10:1767–1778.
MLA Bayrakcı, Mevlüt ve Bahar Yılmaz. “Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base With Biological Application”. Journal of the Institute of Science and Technology, c. 10, sy. 3, 2020, ss. 1767-78, doi:10.21597/jist.679021.
Vancouver Bayrakcı M, Yılmaz B. Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application. Iğdır Üniv. Fen Bil Enst. Der. 2020;10(3):1767-78.