M. Iqbal Choudhary

King Abdulaziz University, Djidda, Makkah, Saudi Arabia

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Publications (874)1353.54 Total impact

  • Atta-ur-Rahman · Muhammad Iqbal Choudhary · Atia-tul-Wahab
    Solving Problems with NMR Spectroscopy, 01/2016: pages 99-132; , ISBN: 9780124115897
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    ABSTRACT: Due to their structural and therapeutic diversity, thienothiophene derivatives have attracted much synthetic interest because of their reactivity and biological activity. The thieno [2,3-b] thiophene moiety has been used in the design of a novel pharmaceutical therapies. Additionally, its enaminones derivatives are versatile synthons and have a lot of synthetic applications such as N-heterocycles, wide variety of naturally occurring alkaloids and pharmaceutical drugs. Synthesis of (2E,2'E)-1,1'-(3,4-diphenylthieno [2,3-b] thiophene-2,5-diyl) bis (3-(dimethylamino) prop-2-en-1-one) 5 was reported. The structure of compound 5 was deduced by spectroscopic techniques. The compound was crystallizes in the monoclinic system with space group P-1 with cell coordinates a=9.9685 (8) Å, b=10.1382 (8) Å, c=13.3220 (11) Å, α=101.018 (2) °, β=94.480 (2) °, γ=107.207 (1) °, V=1249.3 (1) Å3, and Z=2. In the crystal molecules are packed in chains formed via weak intermolecular C21-H21A… O1, C22-H22A…O2 and C27-H27A…O2 hydrogen bondings. Theoretical quantum chemical calculations have been performed on the studied compound using the DFT B3LYP/6-311G (d, p) method. The geometric parameters of the optimized structure are in good agreement with the experimental data obtained from our reported X-ray structure. The two benzene rings and the two side chains are not coplanar with the fused thiophene rings. The electronic spectra of the studied compound have been calculated using the TD-DFT method at the same level of theory. The transition bands at 352.9 nm (f=0.5549) and 332.1 nm (f=0.2190) are due to the H-1 → L (72%) and H → L + 1 (82%) excitations respectively. The NBO calculations were performed to predict the natural atomic charges at the different atomic sites and to study the different intramolecular charge transfer (ICT) interactions occurring in the studied system. It is found that the O and N-atoms have the highest negative charge densities while the S-atoms are the most electropositive. These results give idea about how our molecule could react with the receptor active sites. Compound 5 was evaluated against ant-microbial activity. Synthesis, molecular structure and spectroscopic invesitgation of (2E,2'E)-1,1'-(3,4-diphenylthieno [2,3-b] thiophene-2,5-diyl) bis (3- (dimethylamino) prop-2-en-1-one) 5 was studied. Graphical AbstractMolecular structure investigation of novel enaminone derived from thieno [2,3-b] thiene.
    Chemistry Central Journal 12/2015; 9(1). DOI:10.1186/s13065-015-0100-9 · 2.19 Impact Factor
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    ABSTRACT: Synthesis of (±)-1,3-dimethyl-5-(1-(3-nitrophenyl)-3-oxo-3-phenylpropyl)pyrimidine-2,4,6(1H,3H,5H)-trione (3) is reported. The structure of compound 3 was deduced by using spectroscopic methods, X-ray crystallography, and DFT calculations. The calculated geometric parameters were found to be in good agreement with the experimental data obtained from the X-ray structure. The NBO calculations were performed to predict the natural atomic charges at the different atomic sites and to study the different intramolecular charge transfer (ICT) interactions. The high LP(3)O6 →z BD*(2)O5–N3 ICT interaction energy (165.36 kcal/mol) indicated very strong n → π* electron delocalization while the small LP(2)O → BD*(1)C–H ICT interaction energies indicated that the C–H … O intramolecular interactions are weak. The 1H and 13C NMR chemical shifts calculated using GIAO method showed good agreement with the experimental data. The calculated electronic spectra of the studied compound using TD-DFT method showed intense electronic transition band at 243.9 nm (f = 0.2319) and a shoulder at 260.2 nm (f = 0.1483) which were due to H-4/H-2/H-1/H → L+2 and H-5 → L electronic excitations, respectively. Compound 3 (IC50 = 305 ± 3.8 μM) was identified as a potent inhibitor of α-glucosidase in vitro and showed several fold more inhibition than the standard drug acarbose (IC50 = 841 ± 1.73 μM). Molecular docking of the synthesized compound was discussed.
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    ABSTRACT: Glutinone (1), coixol (2), friedelin (3), glutinol (4), and betulinic acid (5) were isolated from the plant Scoparia dulcis. Their structures were identified using mass and 1D-and 2D-NMR techniques. All the compounds were tested for their immunomodulatory potential in oxidative burst assay. Compound 1 showed a significant inhibitory effect on the release of reactive oxygen species (ROS) from zymosan activated cells from whole blood (IC 50 = 4.3 ± 0.6 µg/mL) as well as from isolated PMNs (IC 50 = 5.0 ± 0.3 µg/mL) as compared to standard drug ibuprofen in whole blood (IC 50 = 11.2± 1.9 µg/ mL) and in isolated PMNs (IC 50 = 2.5± 0.6 µg/mL) shows that it is more active in whole blood as compared with isolated PMNs. Compound 1 when further tested for its effect on pro-inflammatory cytokines TNF-α, IL-1β and on nitric oxide (NO), was found to moderately inhibiting the production of TNF-α (19%) at a concentration 25 µg/mL. On the other hand a weak inhibitory effect of this compound was also observed on the production of IL-1β and NO production, whereas, compounds 2-5 showed no effect (IC 50 = >100) on the release of ROS from zymosan activated cells.
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    ABSTRACT: 2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3±0.11-226.4±6.8μM was observed while comparing these outcomes with the standard acarbose (IC50=906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νCO, νNC and νCH (CH in NCH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds.
    Bioorganic Chemistry 09/2015; 63. DOI:10.1016/j.bioorg.2015.09.001 · 2.15 Impact Factor
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    Letters in Drug Design &amp Discovery 09/2015; 12(999):1-1. DOI:10.2174/1570180812666150907204007 · 0.77 Impact Factor
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    ABSTRACT: We describe here the synthesis of dihydropyrimidines derivatives 3a-p, and evaluationof their α-glucosidase enzyme inhibition activities. Compounds 3b (IC50 = 62.4±1.5 M), 3c (IC50 = 25.3±1.26 M), 3d (IC50 = 12.4±0.15 µM), 3e (IC50 = 22.9±0.25 µM), 3g (IC50 = 23.8±0.17 µM), 3h (IC50 = 163.3±5.1 µM), 3i (IC50 = 30.6±0.6 µM), 3m (IC50 = 26.4±0.34 µM), and 3o (IC50 = 136.1±6.63 µM) were found to be potent α-glucosidase inhibitors in comparison to the standard drug acarbose (IC50 = 840±1.73 µM). The compounds were also evaluated for their in vitro cytotoxic activity against PC-3, HeLa, and MCF-3 cancer cell lines, and 3T3 mouse fibroblast cell line. All compounds were found to be non cytotoxic, except compounds 3f and 3m (IC50 = 17.79±0.66 µM - 20.44±0.30 µM), which showed a weak cytotoxic activity against the HeLa, and 3T3 cell lines. In molecular docking simulation study, all the compounds were docked into the active site of the predicted homology model of α-glucosidaseenzyme. From the docking result, it was observed that most of the synthesized compounds showed interaction through carbonyl oxygen atom and polar phenyl ring with active site residues of the enzyme.
    Bioorganic & Medicinal Chemistry 09/2015; DOI:10.1016/j.bmc.2015.09.001 · 2.79 Impact Factor
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    ABSTRACT: Trimolecular salt Michael adducts 2a-c were synthesized in excellent yields up to 92% via one pot multicomponent reactions in aqueous medium. The chemical structures of compounds 2a-c were characterized by X-ray single-crystal diffraction techniques. Calculations of the density functional theory (DFT) for the synthesized compound were performed. The stability of the products was deduced by TGA analysis. Compounds 2a-c were screened in vitro for different bio-assays such as thymidine phosphorylase inhibition assay, urease inhibition assay, ß-glucuronidase inhibition assays and cytotoxicity against PC-3 and Hela cell lines.
    Research on Chemical Intermediates 08/2015; DOI:10.1007/s11164-015-2257-1 · 1.22 Impact Factor
  • Humera Jahan · M Iqbal Choudhary
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    ABSTRACT: Introduction: The glycation process, comprising a series of reactions, results in the formation of heterogeneous adducts, known as advanced glycation end products (AGEs). AGEs are involved in several pathologies, including diabetes-associated late complications, atherosclerosis, Alzheimer's disease and inflammatory arthritis. Several inhibitors of AGEs and/or reactive carbonyl species have been identified from various sources, including natural products and synthetic molecules, and have been investigated for their mechanism of action. Areas covered: This review covers the literature on AGEs inhibitors published as patents between 2001 and 2014. Initially, the earlier reported molecules with AGEs inhibitory properties, their mechanism of actions and reported adverse effects are discussed. The main focus has been on the chemical structures, methods for evaluation of the activity, modes of action, pharmacokinetics and therapeutic outcomes. The potential of these AGEs inhibitors in the treatment and management of a number of diseases are also discussed in this review. Expert opinion: The reactive carbonyl species and AGEs have recently emerged as novel therapeutic targets for the prevention and treatment of several diseases. Currently, the major concerns with the use of AGEs inhibitors as therapeutic agents are low effectiveness, poor pharmacokinetics and undesirable side effects. Many of the AGEs inhibitors reviewed here possess potent antiglycation activity and are devoid of undesirable side effects. These small molecules inhibitors can, therefore, serve as scaffolds for the development and designing of new AGEs inhibitors as clinical agents.
    Expert Opinion on Therapeutic Patents 08/2015; DOI:10.1517/13543776.2015.1076394 · 4.30 Impact Factor
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    ABSTRACT: Apoptotic cell death is the cause of the loss of insulin-producing β-cells in all forms of diabetes mellitus. The identification of small molecules capable of protecting cytokine-induced apoptosis could form the basis of useful therapeutic interventions. Here in, we present the discovery and synthesis of new benzimidazole derivatives, capable of rescuing pancreatic β-cells from cytokine-induced apoptosis. Three hydrazone derivatives of benzimidazole significantly increased the cellular ATP levels, reduced caspase-3 activity, reduced nitrite production and increased glucose-stimulated insulin secretion in the presence of proinflammatory cytokines. These findings suggest that these compounds may protect β-cells from the harmful effects of cytokines and may serve as candidates for therapeutic intervention for diabetes. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Bioorganic & medicinal chemistry letters 08/2015; DOI:10.1016/j.bmcl.2015.08.022 · 2.42 Impact Factor
  • Industrial Crops and Products 08/2015; 76:749-754. DOI:10.1016/j.indcrop.2015.07.042 · 2.84 Impact Factor
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    ABSTRACT: 2-Arylquinazolin-4(3H)-ones (1-25) were synthesized and evaluated for their xanthine oxidase inhibitory activity with IC50 values in the range of 2.80 ± 0.70 - 112.60 ± 3.01 µM, as compared to the standard, allopurinol (IC50 = 2.01 ± 0.01 µM). Significant to moderate activities were exhibited by the compounds 1-3, 7, 9, 13-15, 19-21, and 23 with IC50 between of 2.8 - 28.13 µM. Compounds 4-6, 8, 11-12, 16-18, 22, and 24 demonstrated a weak activity with IC50 values 44.60 - 112.60 µM. Nonetheless, compounds 10 and 25 did not show any activity. Amongst all derivatives, compound 2, containing a C-4' dimethyl amino group, was the most potent inhibitor of the enzyme with an IC50 value comparable to the standard. Kinetics studies on the most active compounds (2, 7, 9, 14, 15, 19, and 20) were carried out in order to determine their modes of inhibition and dissociation constants Ki. Some of the compounds of 2-arylquinazolin-4(3H)-one series were thus identified as potential leads for further studies towards the treatment of hyperuricemia and gout.
    Medicinal chemistry (Shāriqah (United Arab Emirates)) 08/2015; 11(999):1-1. DOI:10.2174/1573406410666150807111336 · 1.36 Impact Factor
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    ABSTRACT: This article describes discovery of 29 novel bisindolylmethanes consisting of thiourea moiety, which had been synthesized through three steps. These novel bisindolylmethane derivatives evaluated for their potential inhibitory activity against carbonic anhydrase (CA) II. The results for in vitro assay of carbonic anhydrase II inhibition activity showed that some of the compounds are capable of suppressing the activity of carbonic anhydrase II. Bisindoles having halogen at fifth position showed better inhibitory activity as compared to unsubstituted bisindoles. Derivatives showing inhibition activity docked to further, understand the binding behavior of these compounds with carbonic anhydrase II. Docking studies for the active compound 3j showed that nitro substituent at para position fits into the core of the active site. The nitro substituent of compound 3j is capable of interacting with Zn ion. This interaction believed to be the main factor causing inhibition activity to take place. Copyright © 2015 Elsevier Inc. All rights reserved.
    Bioorganic Chemistry 08/2015; 62. DOI:10.1016/j.bioorg.2015.08.001 · 2.15 Impact Factor
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    ABSTRACT: Abstract CONTEXT: During diabetes mellitus, non-enzymatic reaction between amino groups of protein and carbonyl of reducing sugars (Millard reaction) is responsible for the major diabetic complications. Various efforts have been made to influence the process of protein glycation. OBJECTIVES: This review article provides an extensive survey of various studies published in scientific literature to understand the process of protein glycation and its measurement. Moreover, evaluation and identification of potential inhibitors (antiglycation agents) of protein glycation from natural and synthetic sources and their mechanism of action in vitro and in vivo are also addressed. METHOD: In this review article, the mechanism involved in the formation of advanced glycation end products (AGEs) is discussed, while in second and third parts, promising antiglycation agents of natural and synthetic sources have been reviewed, respectively. Finally, in vivo studies have been addressed. This review is mainly compiled from important databases such as Science, Direct, Chemical Abstracts, SciFinder, and PubMed. RESULTS: During the last two decades, various attempts have been made to inhibit the process of protein glycation. New potent inhibitors of protein glycation belonging to different classes such as flavonoids, alkaloids, terpenes, benzenediol Schiff bases, substituted indol, and thio compounds have been identified. CONCLUSION: Antiglycation therapy will be an effective strategy in future to prevent the formation of AGEs for the management of late diabetic complications Current review article highlighted various compounds of natural and synthetic origins identified previously to inhibit the protein glycation and formation of AGEs in vitro and in vivo. KEYWORDS: Advanced glycation end products; antiglycation activity; hyperglycemia; protein glycation; reducing sugars
    Pharmaceutical Biology 08/2015; · 1.24 Impact Factor
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    ABSTRACT: In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomodulatory activities. The compounds were found to be moderately active only against leishmania. Within this series, compound 26 was found to be the most active antileishaminals with IC50 value 37.4 ± 0.4 μM. Structure-activity relationships for this novel class are discussed.
    Letters in Drug Design &amp Discovery 08/2015; 12(7). DOI:10.2174/1570180812999150225111959 · 0.77 Impact Factor
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    Bashir Ahmad · Sadiq Azam · Shumaila Bashir · Achyut Adhikari · M Iqbal Choudhary
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    ABSTRACT: Ethno-botanical inspired isolation from plant Scoparia dulcis Linn. (Sweet Broomweed) yielded six compounds, coixol (1), glutinol (2), glutinone (3), friedelin (4), betulinic acid (5), and tetratriacontan-1-ol (6). There structures were identified using mass and 1D- and 2D-NMR spectroscopy techniques. Compounds 1-6 were evaluated for their insulin secretory activity on isolated mice islets and MIN-6 pancreatic β-cell line, and compounds 1 and 2 were found to be potent and mildly active, respectively. Compound 1 was further evaluated for insulin secretory activity on MIN-6 cells. Compound 1 was subjected to in vitro cytotoxicity assay against MIN-6, 3T3 cell lines, and islet cells, and in vivo acute toxicity test in mice that was found to be non-toxic. The insulin secretory activity of compounds 1 and 2 supported the ethno-botanic uses of S. dulcis as an anti-diabetic agent. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.
    Phytotherapy Research 07/2015; DOI:10.1002/ptr.5412 · 2.66 Impact Factor
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    ABSTRACT: In the continuation of our work to synthesize enzyme inhibitors. We synthesized 3,4,5-trihydroxybenzohydrazones (1-19) from 3,4,5-trihydroxybenzohydrazide, which were obtained from methyl 3,4,5-trihydroxybenzoate by refluxing with hydrazine hydrate. All the synthesized compounds were characterized by different spectroscopic methods. The synthesized compounds were evaluated for urease inhibition and showed excellent results, closed to the standards thiourea. The kinetics studies on the five most active compounds 6, 10, 14, 16 and 18 were carried out to determine their mode of inhibition and dissociation constant Ki. The compounds 6 and 16 were found to be competitive inhibitors with Ki values 19.1 and 10.53 μM, respectively, while the compounds 10, 14 and 18 were found to be mixed-type of inhibitors with Ki values in the range of 18.4- 21.7 μM.
    Arabian Journal of Chemistry 07/2015; 23. DOI:10.1016/j.arabjc.2015.06.036 · 3.73 Impact Factor
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    ABSTRACT: Phenyl thiazole hydrazone derivatives 1–21 have been synthesized and screened for their in vitro antiglycation activity. Hydrazones 1–21 displayed assorted antiglycation activities having IC50 values in the range of 187.61 ± 1.12–886.98 ± 5.29 µM as compared to standard rutin (IC50 = 269.07 ± 3.79 µM). Compounds 5 (IC50 = 187.61 ± 1.12 µM), 3 (IC50 = 191.92 ± 3.08 µM), 4 (IC50 = 193.77 ± 3.06 µM), 6 (IC50 = 217.90 ± 2.48 µM), 15 (IC50 = 221.98 ± 2.34 µM), 2 (IC50 = 226.59 ± 1.19 µM), 21 (IC50 = 229.67 ± 1.95 µM), 18 (IC50 = 231.09 ± 0.38 µM), 12 (IC50 = 242.94 ± 2.05 µM), and 1 (IC50 = 264.22 ± 5.60 µM), respectively, showed excellent antiglycation activities superior to standard rutin. Compound 17 (IC50 = 269.94 ± 1.11 µM) demonstrated a comparable activity to the standard. Compounds 7, 8, 9, 10, 11, 13, 14, and 16 exhibited weaker activities than standard. However, compounds 19 and 20 showed no activity. When evaluated for cytotoxicity against rat fibroblast cell line (3T3 cell line), all compounds were found to be non-toxic in cellular model.
    Medicinal Chemistry Research 07/2015; 24(7):3077-3085. DOI:10.1007/s00044-015-1349-1 · 1.40 Impact Factor

Publication Stats

7k Citations
1,353.54 Total Impact Points


  • 2012–2015
    • King Abdulaziz University
      • Department of Biochemistry
      Djidda, Makkah, Saudi Arabia
    • Université de Dschang
      • Department of Biochemistry
      Tchang, West Region, Cameroon
  • 2010–2015
    • King Saud University
      • Department of Chemistry
      Ar Riyāḑ, Ar Riyāḑ, Saudi Arabia
    • University of Peradeniya
      • Department of Chemistry
      Mahanuvara, Central, Sri Lanka
    • Quaid-i-Azam University
      • Department of Chemistry
      Islāmābād, Islamabad Capital Territory, Pakistan
  • 2006–2015
    • University of Yaoundé II
      Jaúnde, Centre, Cameroon
    • The Islamia University of Bahawalpur
      • Department of Pharmacy
      Бахавалпура, Punjab, Pakistan
  • 1994–2015
    • H.E.J. Research Institute of Chemistry
      Kurrachee, Sindh, Pakistan
  • 1986–2015
    • University of Karachi
      • • International Center for Chemical and Biological Sciences
      • • Dr. Panjwani Center for Molecular Medicine and Drug Research
      • • HEJ Research Institute of Chemistry
      Kurrachee, Sindh, Pakistan
  • 2014
    • University of Agriculture Faisalabad
      • Department of Chemistry and Biochemistry
      Shah Faisalabad, Punjab, Pakistan
  • 2011
    • Putra University, Malaysia
      • Institute of Bioscience
      Putrajaya, Putrajaya, Malaysia
  • 2005–2010
    • University of Tuebingen
      • Institute of Physical and Theoretical Chemistry
      Tübingen, Baden-Württemberg, Germany
    • University of Science Malaysia
      • School of Physics
      Nibong Tepal, Penang, Malaysia
    • Universität Paderborn
      • Department of Chemistry
      Paderborn, North Rhine-Westphalia, Germany
  • 2003–2010
    • The University of Calgary
      • Department of Chemistry
      Calgary, Alberta, Canada
  • 2009
    • Beni Suef University
      • Faculty of Pharmacy
      Beni Suef, Banī Suwayf, Egypt
  • 2007–2009
    • University of Douala
      • • Department of Chemistry
      • • Department of Biochemistry
      Duala, Littoral Province, Cameroon
  • 2008
    • University of Science & Technology Bannu
      • Department of Chemistry
      Bannu, Khyber Pakhtunkhwa, Pakistan
    • University of Vermont
      • Department of Chemistry
      Burlington, VT, United States
    • University of Peshawar
      • Centre of Biotechnology and Microbiology
      Peshāwar, North West Frontier Province, Pakistan
    • Institute of Medical Research and Studies on Medicinal Plants
      Jaúnde, Centre Region, Cameroon
  • 2007–2008
    • Bielefeld University
      • Organic Chemistry
      Bielefeld, North Rhine-Westphalia, Germany
    • Tribhuvan University
      • Institute of Forestry
      Kantipura, Central Region, Nepal
  • 2004
    • Al-Farabi Kazakh National University
      Almaty, Almaty Qalasy, Kazakhstan
  • 2002–2004
    • University of Dhaka
      • Department of Chemistry
      Mujib City, Dhaka, Bangladesh
    • Anadolu University
      Eski-chéhir, Eskişehir, Turkey
    • The University of Winnipeg
      • Department of Chemistry
      Winnipeg, Manitoba, Canada
  • 1986–2004
    • Pennsylvania State University
      • Department of Chemistry
      University Park, Maryland, United States
  • 1995
    • University of Jordan
      • Department of Chemistry
      Amman, Amman, Jordan
  • 1988–1995
    • Cornell University
      Итак, New York, United States
  • 1992
    • Gazi University
      • Department of Pharmacognosy
      Engüri, Ankara, Turkey