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Morin'in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri

Year 2019, Volume: 9 Issue: 3, 1443 - 1451, 01.09.2019
https://doi.org/10.21597/jist.521686

Abstract

Biyoaktif flavonoidler, insan için birçok biyolojik faydalar sağlayan gıdadaki en önemli fitokimyasallar olarak kabul edilir. Antioksidan, anti-bakteriyel, anti-kolinerjik, anti-diyabetik, anti-mutajenik ve anti-enflamatuar özellikler gibi birçok farmakolojik aktiviteye sahiptirler. Flavonoidlerin bir üyesi olan morin, nükleik asitler, enzimler ve proteinler ile etkileĢime girerek birçok terapötik özellik sergiler. Bu çalıĢmada, doğal fenolik bir bileĢik olarak morin, insan karbonik anhidraz (CA) izoformları I ve II (CA I ve II), asetilkolinesteraz (AChE) ve 𝛼-glikozidaz enzimlerine karĢı inhibe edici etkiler göstermiĢtir. Bu fenolik bileĢik, CA I, CA II, AChE ve 𝛼-glikozidaz enzimlerinin inhibisyonu için test edildi ve sırasıyla CA I için 31.89 ± 9.07 nM, CA II için 49.25 ± 12.85 nM, AChE için 184.67 ± 30.37 nM ve 𝛼-glikozidaz için 16.99 ± 4.40 nM Ki değerleri ile etkili inhibisyon profilleri gösterdi.

References

  • Aksu K, Akıncıoğlu H, Akıncıoğlu A, Göksu S, Tümer F, Gülçin İ, 2018. Synthesis of novel sulfamides incorporating phenethylamines and determination of their inhibition profiles against some metabolic enzymes. Archiv der Pharmazie, 351(9): 1800150.
  • Aktaş A, Celepci DB, Kaya R, Taslimi P, Gök Y, Aygün M, Gülçin İ, 2019. Novel morpholine liganded Pd-based N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, antidiabetic and anticholinergic properties. Polyhedron, 159: 345-354.
  • Benzer F, Kandemir FM, Kucukler S, Comaklı S, Caglayan C, 2018. Chemoprotective effects of curcumin on doxorubicin-induced nephrotoxicity in wistar rats: by modulating inflammatory cytokines, apoptosis, oxidative stress and oxidative DNA damage. Archives of Physiology and Biochemistry, 124(5): 448-457.
  • Caglayan C, Demir Y, Kucukler S, Taslimi P, Kandemir FM, Gulçin İ, 2018a. The effects of hesperidin on sodium arsenite‐induced different organ toxicity in rats on metabolic enzymes as antidiabetic and anticholinergics potentials: A biochemical approach. Journal of Food Biochemistry, e12720.
  • Caglayan C, Gulcin İ, 2018. The toxicological effects of some avermectins on goat liver carbonic anhydrase enzyme. Journal of biochemical and molecular toxicology, 32(1): e22010.
  • Caglayan C, Temel Y, Kandemir FM, Yildirim S, Kucukler S, 2018b. Naringin protects against cyclophosphamide-induced hepatotoxicity and nephrotoxicity through modulation of oxidative stress, inflammation, apoptosis, autophagy, and DNA damage. Environmental Science and Pollution Research, 25(21): 20968-20984.
  • Eldutar E, Kandemir FM, Kucukler S, Caglayan C, 2017. Restorative effects of Chrysin pretreatment on oxidant–antioxidant status, inflammatory cytokine production, and apoptotic and autophagic markers in acute paracetamol‐induced hepatotoxicity in rats: An experimental and biochemical study. Journal of biochemical and molecular toxicology, 31: e21960.
  • Ellman GL, Courtney KD, Andres JV, Featherstone RM, 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical pharmacology, 7(2): 88-95.
  • Gopal JV, 2013. Morin hydrate: Botanical origin, pharmacological activity and its applications: A mini-review. Pharmacognosy Journal, 5: 123-126.
  • Gulçin İ, Abbasova M, Taslimi P, Huyut Z, Safarova L, Sujayev A, Farzaliyev V, Beydemir Ş, Alwasel SH, Supuran CT, 2017. Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 32: 1174-1182.
  • Gülçin İ, Scozzafava A, Supuran CT, Koksal Z, Turkan F, Çetinkaya S, Bingöl Z, Huyut Z, Alwasel SH, 2016. Rosmarinic acid inhibits some metabolic enzymes including glutathione S-transferase, lactoperoxidase, acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 1698-1702.
  • Huyut Z, Beydemir Ş, Gülçin İ, 2017. Inhibition properties of some flavonoids on carbonic anhydrase I and II isoenzymes purified from human erythrocytes. J Journal of biochemical and molecular toxicology, 31: e21930.
  • Kandemir FM, Kucukler S, Eldutar E, Caglayan C, Gülçin I, 2017a. Chrysin protects rat kidney from paracetamol-induced oxidative stress, inflammation, apoptosis, and autophagy: A Multi-biomarker approach. Scientia pharmaceutica, 85(1): 4.
  • Kandemir FM, Ozkaraca M, Küçükler S, Caglayan C, Hanedan B, 2017b. Preventive effects of hesperidin on diabetic nephropathy induced by streptozotocin via modulating TGF-β1 and oxidative DNA damage. Toxin reviews, 37(4): 287-293.
  • Kaygusuzoglu E, Caglayan C, Kandemir FM, Yıldırım S, Kucukler S, Kılınc MA, Saglam YS, 2018. Zingerone ameliorates cisplatin‐induced ovarian and uterine toxicity via suppression of sex hormone imbalances, oxidative stress, inflammation and apoptosis in female wistar rats. Biomedicine and Pharmacotherapy, 102: 517-530.
  • Kim JM, Lee EK, Park G, Kim MK, Yokozawa T, Yu BP, Chung HY, 2010. Morin modulates the oxidative stress-induced NF-κB pathway through its anti-oxidant activity. Free radical research, 44(4): 454-461.
  • Köksal E, Bursal E, Gülçin İ, Korkmaz M, Çağlayan C, Gören AC, Alwasel SH, 2017. Antioxidant activity and polyphenol content of Turkish thyme (Thymus vulgaris) monitored by liquid chromatography and tandem mass spectrometry. International Journal of Food Properties, 20(3): 514-525.
  • Kuzu M, Kandemir FM, Yildirim S, Kucukler S, Caglayan C, Turk E, 2018. Morin attenuates doxorubicin-induced heart and brain damage by reducing oxidative stress, inflammation and apoptosis. Biomedicine and Pharmacotherapy, 106: 443-453.
  • Laemmli UK, 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227: 680.
  • Lineweaver H, Burk D, 1934. The determination of enzyme dissociation constants. Journal of the American chemical society, 56(3): 658-666.
  • McDougall GJ, Shpiro F, Dobson P, Smith P, Blake A, Stewart D, 2005. Different polyphenolic components of soft fruits inhibit α-amylase and α-glucosidase. Journal of agricultural and food chemistry, 53(7): 2760-2766.
  • Olonode ET, Aderibigbe AO, Adeoluwa OA, Eduviere AT, Ben-Azu B, 2019. Morin hydrate mitigates rapid eye movement sleep deprivation-induced neurobehavioural impairments and loss of viable neurons in the hippocampus of mice. Behavioural brain research, 356: 518-525.
  • Tao Y, Zhang Y, Cheng Y, Wang Y, 2013. Rapid screening and identification of α‐glucosidase inhibitors from mulberry leaves using enzyme‐immobilized magnetic beads coupled with HPLC/MS and NMR. Biomedical Chromatography, 27(2): 148-155.
  • Taslimi P, Caglayan C, Gulcin İ, 2017. The impact of some natural phenolic compounds on carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes: An antidiabetic, anticholinergic, and antiepileptic study. Journal of biochemical and molecular toxicology, 31: e21995.
  • Taslimi P, Caglayan C, Farzaliyev V, Nabiyev O, Sujayev A, Turkan F, Kaya R, Gulçin İ. 2018a. Synthesis and discovery of potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes inhibitors: The novel N, N′‐bis‐cyanomethylamine and alkoxymethylamine derivatives. Journal of biochemical and molecular toxicology, 32: e22042.
  • Taslimi P, Osmanova S, Caglayan C, Turkan F, Sardarova S, Farzaliyev V, Sujayev A, Sadeghian N, Gulçin İ, 2018b. Novel amides of 1, 1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties. Journal of biochemical and molecular toxicology, 32: e22191.
  • Taslimi P, Kandemir FM, Demir Y, İleritürk M, Temel Y, Caglayan C, Gulçin, İ. 2019. The antidiabetic and anticholinergic effects of chrysin on cyclophosphamide‐induced multiple organ toxicity in rats: Pharmacological evaluation of some metabolic enzyme activities. Journal of Biochemical and Molecular Toxicology, e22313.
  • Topal F, Gulcin I, Dastan A, Guney M, 2017. Novel eugenol derivatives: Potent acetylcholinesterase and carbonic anhydrase inhibitors. International Journal of Biological Macromolecular, 94: 845-851.
  • Topal M, Gülçin İ, 2014. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turkish journal of chemistry, 38: 894-902.
  • Türkan F, Huyut Z, Taslimi P, Gülçin İ, 2018a. The in vivo effects of cefazolin, cefuroxime, and cefoperazon on the carbonic anhydrase in different rat tissues. J Journal of biochemical and molecular toxicology, 32: e22041.
  • Türkan F, Huyut Z, Taslimi P, Gülçin İ, 2018b. The effects of some antibiotics from cephalosporin groups on the acetylcholinesterase and butyrylcholinesterase enzymes activities in different tissues of rats. Archives of physiology and biochemistry, 1-7.
  • Verpoorte JA, Mehta S, Edsall JT, 1967. Esterase activities of human carbonic anhydrases B and C. Journal of Biological Chemistry, 242(18): 4221-4229.
  • Xu P, Wu J, Zhang Y, Chen H, Wang Y, 2014. Physicochemical characterization of puerh tea polysaccharides and their antioxidant and α-glycosidase inhibition. Journal of Functional Foods, 6: 545-554.
  • Zhang L, Hogan S, Li J, Sun S, Canning C, Zheng SJ, Zhou K, 2011. Grape skin extract inhibits mammalian intestinal α-glucosidase activity and suppresses postprandial glycemic response in streptozocin-treated mice. Food Chemistry. 126: 466-471.

Inhibition Effects of Morin on Carbonic Anhydrase, Acetylcholinesterase and 𝛼-glycosidase Enzymes

Year 2019, Volume: 9 Issue: 3, 1443 - 1451, 01.09.2019
https://doi.org/10.21597/jist.521686

Abstract

Bioactive flavonoids are considered to be the most important phytochemicals in food that provide many biological benefits for human beings. They have many pharmacological activities that include antioxidant, anti-bacterial, anti-cholinergic, anti-diabetic, anti-mutagenic and anti-inflammatory properties. Morin, a member of flavonoids, exhibit many therapeutic properties by interacting with nucleic acids, enzymes and protein. In this study, morin as natural a phenolic compound showed inhibitory effects against human carbonic anhydrase (CA) isoforms I and II (CA I and II), acetylcholinesterase (AChE) and 𝛼-glycosidase enzymes. This phenolic compound was tested for the inhibition of CA I, CA II, AChE, and 𝛼-glycosidase enzymes and demonstrated efficient inhibition profiles with Ki value of 31.89 ± 9.07 nM for CA I, 49.25 ± 12.85 nM for CA II, 184.67 ± 30.37 nM for AChE, and 16.99 ± 4.40 nM for 𝛼-glycosidase, respectively.

References

  • Aksu K, Akıncıoğlu H, Akıncıoğlu A, Göksu S, Tümer F, Gülçin İ, 2018. Synthesis of novel sulfamides incorporating phenethylamines and determination of their inhibition profiles against some metabolic enzymes. Archiv der Pharmazie, 351(9): 1800150.
  • Aktaş A, Celepci DB, Kaya R, Taslimi P, Gök Y, Aygün M, Gülçin İ, 2019. Novel morpholine liganded Pd-based N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, antidiabetic and anticholinergic properties. Polyhedron, 159: 345-354.
  • Benzer F, Kandemir FM, Kucukler S, Comaklı S, Caglayan C, 2018. Chemoprotective effects of curcumin on doxorubicin-induced nephrotoxicity in wistar rats: by modulating inflammatory cytokines, apoptosis, oxidative stress and oxidative DNA damage. Archives of Physiology and Biochemistry, 124(5): 448-457.
  • Caglayan C, Demir Y, Kucukler S, Taslimi P, Kandemir FM, Gulçin İ, 2018a. The effects of hesperidin on sodium arsenite‐induced different organ toxicity in rats on metabolic enzymes as antidiabetic and anticholinergics potentials: A biochemical approach. Journal of Food Biochemistry, e12720.
  • Caglayan C, Gulcin İ, 2018. The toxicological effects of some avermectins on goat liver carbonic anhydrase enzyme. Journal of biochemical and molecular toxicology, 32(1): e22010.
  • Caglayan C, Temel Y, Kandemir FM, Yildirim S, Kucukler S, 2018b. Naringin protects against cyclophosphamide-induced hepatotoxicity and nephrotoxicity through modulation of oxidative stress, inflammation, apoptosis, autophagy, and DNA damage. Environmental Science and Pollution Research, 25(21): 20968-20984.
  • Eldutar E, Kandemir FM, Kucukler S, Caglayan C, 2017. Restorative effects of Chrysin pretreatment on oxidant–antioxidant status, inflammatory cytokine production, and apoptotic and autophagic markers in acute paracetamol‐induced hepatotoxicity in rats: An experimental and biochemical study. Journal of biochemical and molecular toxicology, 31: e21960.
  • Ellman GL, Courtney KD, Andres JV, Featherstone RM, 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical pharmacology, 7(2): 88-95.
  • Gopal JV, 2013. Morin hydrate: Botanical origin, pharmacological activity and its applications: A mini-review. Pharmacognosy Journal, 5: 123-126.
  • Gulçin İ, Abbasova M, Taslimi P, Huyut Z, Safarova L, Sujayev A, Farzaliyev V, Beydemir Ş, Alwasel SH, Supuran CT, 2017. Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 32: 1174-1182.
  • Gülçin İ, Scozzafava A, Supuran CT, Koksal Z, Turkan F, Çetinkaya S, Bingöl Z, Huyut Z, Alwasel SH, 2016. Rosmarinic acid inhibits some metabolic enzymes including glutathione S-transferase, lactoperoxidase, acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase isoenzymes. Journal of Enzyme Inhibition and Medicinal Chemistry, 31: 1698-1702.
  • Huyut Z, Beydemir Ş, Gülçin İ, 2017. Inhibition properties of some flavonoids on carbonic anhydrase I and II isoenzymes purified from human erythrocytes. J Journal of biochemical and molecular toxicology, 31: e21930.
  • Kandemir FM, Kucukler S, Eldutar E, Caglayan C, Gülçin I, 2017a. Chrysin protects rat kidney from paracetamol-induced oxidative stress, inflammation, apoptosis, and autophagy: A Multi-biomarker approach. Scientia pharmaceutica, 85(1): 4.
  • Kandemir FM, Ozkaraca M, Küçükler S, Caglayan C, Hanedan B, 2017b. Preventive effects of hesperidin on diabetic nephropathy induced by streptozotocin via modulating TGF-β1 and oxidative DNA damage. Toxin reviews, 37(4): 287-293.
  • Kaygusuzoglu E, Caglayan C, Kandemir FM, Yıldırım S, Kucukler S, Kılınc MA, Saglam YS, 2018. Zingerone ameliorates cisplatin‐induced ovarian and uterine toxicity via suppression of sex hormone imbalances, oxidative stress, inflammation and apoptosis in female wistar rats. Biomedicine and Pharmacotherapy, 102: 517-530.
  • Kim JM, Lee EK, Park G, Kim MK, Yokozawa T, Yu BP, Chung HY, 2010. Morin modulates the oxidative stress-induced NF-κB pathway through its anti-oxidant activity. Free radical research, 44(4): 454-461.
  • Köksal E, Bursal E, Gülçin İ, Korkmaz M, Çağlayan C, Gören AC, Alwasel SH, 2017. Antioxidant activity and polyphenol content of Turkish thyme (Thymus vulgaris) monitored by liquid chromatography and tandem mass spectrometry. International Journal of Food Properties, 20(3): 514-525.
  • Kuzu M, Kandemir FM, Yildirim S, Kucukler S, Caglayan C, Turk E, 2018. Morin attenuates doxorubicin-induced heart and brain damage by reducing oxidative stress, inflammation and apoptosis. Biomedicine and Pharmacotherapy, 106: 443-453.
  • Laemmli UK, 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227: 680.
  • Lineweaver H, Burk D, 1934. The determination of enzyme dissociation constants. Journal of the American chemical society, 56(3): 658-666.
  • McDougall GJ, Shpiro F, Dobson P, Smith P, Blake A, Stewart D, 2005. Different polyphenolic components of soft fruits inhibit α-amylase and α-glucosidase. Journal of agricultural and food chemistry, 53(7): 2760-2766.
  • Olonode ET, Aderibigbe AO, Adeoluwa OA, Eduviere AT, Ben-Azu B, 2019. Morin hydrate mitigates rapid eye movement sleep deprivation-induced neurobehavioural impairments and loss of viable neurons in the hippocampus of mice. Behavioural brain research, 356: 518-525.
  • Tao Y, Zhang Y, Cheng Y, Wang Y, 2013. Rapid screening and identification of α‐glucosidase inhibitors from mulberry leaves using enzyme‐immobilized magnetic beads coupled with HPLC/MS and NMR. Biomedical Chromatography, 27(2): 148-155.
  • Taslimi P, Caglayan C, Gulcin İ, 2017. The impact of some natural phenolic compounds on carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes: An antidiabetic, anticholinergic, and antiepileptic study. Journal of biochemical and molecular toxicology, 31: e21995.
  • Taslimi P, Caglayan C, Farzaliyev V, Nabiyev O, Sujayev A, Turkan F, Kaya R, Gulçin İ. 2018a. Synthesis and discovery of potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes inhibitors: The novel N, N′‐bis‐cyanomethylamine and alkoxymethylamine derivatives. Journal of biochemical and molecular toxicology, 32: e22042.
  • Taslimi P, Osmanova S, Caglayan C, Turkan F, Sardarova S, Farzaliyev V, Sujayev A, Sadeghian N, Gulçin İ, 2018b. Novel amides of 1, 1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties. Journal of biochemical and molecular toxicology, 32: e22191.
  • Taslimi P, Kandemir FM, Demir Y, İleritürk M, Temel Y, Caglayan C, Gulçin, İ. 2019. The antidiabetic and anticholinergic effects of chrysin on cyclophosphamide‐induced multiple organ toxicity in rats: Pharmacological evaluation of some metabolic enzyme activities. Journal of Biochemical and Molecular Toxicology, e22313.
  • Topal F, Gulcin I, Dastan A, Guney M, 2017. Novel eugenol derivatives: Potent acetylcholinesterase and carbonic anhydrase inhibitors. International Journal of Biological Macromolecular, 94: 845-851.
  • Topal M, Gülçin İ, 2014. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turkish journal of chemistry, 38: 894-902.
  • Türkan F, Huyut Z, Taslimi P, Gülçin İ, 2018a. The in vivo effects of cefazolin, cefuroxime, and cefoperazon on the carbonic anhydrase in different rat tissues. J Journal of biochemical and molecular toxicology, 32: e22041.
  • Türkan F, Huyut Z, Taslimi P, Gülçin İ, 2018b. The effects of some antibiotics from cephalosporin groups on the acetylcholinesterase and butyrylcholinesterase enzymes activities in different tissues of rats. Archives of physiology and biochemistry, 1-7.
  • Verpoorte JA, Mehta S, Edsall JT, 1967. Esterase activities of human carbonic anhydrases B and C. Journal of Biological Chemistry, 242(18): 4221-4229.
  • Xu P, Wu J, Zhang Y, Chen H, Wang Y, 2014. Physicochemical characterization of puerh tea polysaccharides and their antioxidant and α-glycosidase inhibition. Journal of Functional Foods, 6: 545-554.
  • Zhang L, Hogan S, Li J, Sun S, Canning C, Zheng SJ, Zhou K, 2011. Grape skin extract inhibits mammalian intestinal α-glucosidase activity and suppresses postprandial glycemic response in streptozocin-treated mice. Food Chemistry. 126: 466-471.
There are 34 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Cüneyt Çağlayan 0000-0001-5608-554X

Publication Date September 1, 2019
Submission Date February 4, 2019
Acceptance Date March 7, 2019
Published in Issue Year 2019 Volume: 9 Issue: 3

Cite

APA Çağlayan, C. (2019). Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri. Journal of the Institute of Science and Technology, 9(3), 1443-1451. https://doi.org/10.21597/jist.521686
AMA Çağlayan C. Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri. J. Inst. Sci. and Tech. September 2019;9(3):1443-1451. doi:10.21597/jist.521686
Chicago Çağlayan, Cüneyt. “Morin’in Karbonik Anhidraz, Asetilkolinesteraz Ve 𝛼-Glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri”. Journal of the Institute of Science and Technology 9, no. 3 (September 2019): 1443-51. https://doi.org/10.21597/jist.521686.
EndNote Çağlayan C (September 1, 2019) Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri. Journal of the Institute of Science and Technology 9 3 1443–1451.
IEEE C. Çağlayan, “Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri”, J. Inst. Sci. and Tech., vol. 9, no. 3, pp. 1443–1451, 2019, doi: 10.21597/jist.521686.
ISNAD Çağlayan, Cüneyt. “Morin’in Karbonik Anhidraz, Asetilkolinesteraz Ve 𝛼-Glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri”. Journal of the Institute of Science and Technology 9/3 (September 2019), 1443-1451. https://doi.org/10.21597/jist.521686.
JAMA Çağlayan C. Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri. J. Inst. Sci. and Tech. 2019;9:1443–1451.
MLA Çağlayan, Cüneyt. “Morin’in Karbonik Anhidraz, Asetilkolinesteraz Ve 𝛼-Glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri”. Journal of the Institute of Science and Technology, vol. 9, no. 3, 2019, pp. 1443-51, doi:10.21597/jist.521686.
Vancouver Çağlayan C. Morin’in Karbonik Anhidraz, Asetilkolinesteraz ve 𝛼-glikozidaz Enzimleri Üzerindeki İnhibisyon Etkileri. J. Inst. Sci. and Tech. 2019;9(3):1443-51.