M Iqbal Choudhary

King Abdulaziz University, Djidda, Makkah, Saudi Arabia

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Publications (564)952.34 Total impact

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    [Show abstract] [Hide abstract]
    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 · 1.66 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; · 1.34 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 · 0.96 Impact Factor
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    ABSTRACT: Microbial transformation of oxandrolone (1) was carried out by using Cunninghamella blakesleeana and Macrophomina phaseolina. Biotransformation of 1 with M. phaseolina yielded four new metabolites, 11β,17β-dihydroxy-17α-(hydroxymethyl)-2-oxa-5α-androstan-3-one (2), 5α,11β,17β-trihydroxy-17α-methyl-2-oxa-androstan-3-one (3), 17β-hydroxy-17α-methyl-2-oxa-5α-androstan-3,11-dione (4), and 11β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one (5). Whereas a new metabolite, 12β,17β-dihydroxy-17α-methyl-2-oxa-5α-androstan-3-one (6), was obtained through the microbial transformation of oxandrolone (1) with Cunninghamella blakesleeana. The structures of isolated metabolites were characterized on the basis of MS and NMR spectroscopic data. Copyright © 2015. Published by Elsevier Inc.
    Steroids 06/2015; DOI:10.1016/j.steroids.2015.06.008 · 2.72 Impact Factor
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    ABSTRACT: Background: 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. Results: 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. Conclusions: 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. Keywords: Enaminones, Thieno [2,3-b] thiophene, X-ray, HOMO, LUMO
    Chemistry Central Journal 06/2015; 9:24:1-11. · 1.66 Impact Factor
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    ABSTRACT: Lichens are the symbiotic association of fungi and algae, and produce interesting and characteristic secondary metabolites. The structure-fragmentation relationship (SFR) of ten secondary metabolites from various classes, including monocyclic phenol, depside, depsidones, and dibenzofuran were investigated by using negative mode electrospray quadrupole time-of-flight mass spectrometry (ESI-QqTOF-MS/MS). Low energy collision induced dissociation tandem mass spectrometric analysis of these deprotonated molecules yielded key fragments due to the loss of neutral components like CO, CO2, methanol, ethanol, and ethene. Interestingly, odd electron fragments were also observed in sekikaic acid, lobaric acid, and usnic acid as a characteristic fragments. Fragmentation pattern of standard compounds, high resolution analysis and database were used for the rapid identification of lichen compounds in lichen species, Parmotrema grayana and Heterdermia obscurata. Furthermore MS/MS spectra revealed different fragmentation pathways for different classes of secondary metabolites. Total fifteen compounds were identified from the methanolic and dichloromethane extracts of Parmotrema grayana, and Heterdermia obscurata.
    Analytical methods 06/2015; DOI:10.1039/C5AY01091H · 1.94 Impact Factor
  • Letters in Drug Design &amp Discovery 05/2015; 12(999):1-1. DOI:10.2174/1570180812666150520001629 · 0.96 Impact Factor
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    ABSTRACT: A dichloromethane–acetone extract of Euphorbia osyridea Bioss. (Syn. Euphorbia lateriflora Schumach. & Thonn), a spurge endemic to Iran and West Africa, afforded three new jatrophane diterpenes belonging to the 2,3,5,7,8,9,14,15-octahydroxy-jatropha-6(17),11E-diene class along with three known triterpenes. Structures of these compounds were elucidated by spectroscopic methods, especially 2D NMR analyses. Biological effects of these compounds were analyzed by performing MTT and annexin V-FITC and PI staining assays against different cancer cell lines. Results showed that 2,3,5,7,8,9,14,15-octahydroxy-jatropha-6(17), 11E-diene derivatives (1–3) inhibit the cell proliferation through apoptosis in the Caov-4 and OVCAR-3 cancer cell lines.
    Phytochemistry Letters 05/2015; 12. DOI:10.1016/j.phytol.2015.04.011 · 1.54 Impact Factor
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  • Pharmaceutical Biology 04/2015; · 1.34 Impact Factor
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    [Show abstract] [Hide abstract]
    ABSTRACT: 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. 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. 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. 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. 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.
    Pharmaceutical Biology 04/2015; DOI:10.3109/13880209.2015.1028080 · 1.34 Impact Factor
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    ABSTRACT: A new isoflavone 7-hydroxy 30-methoxyisoflavone (1) is isolated from the seeds of Indigofera heterantha. The structure of this new compound was established using spectroscopic techniques such as ID, 2D NMR, and mass spectrometry. Density functional theory calculations are carried out for the first time for geometric, electronic and spectroscopic properties of 1 (isoflavone). DFT calculations have been performed at B3LYP/6-311G(d,p) level of theory for obtaining geometric and spectroscopic properties of compound 1. The simulated vibrational spectrum of compound 1 at B3LYP/6-311G(d,p) shows nice correlation with the experimental IR spectrum after a scaling factor of 0.973. 1H and 13C NMR chemical shifts were calculated using Cramer’s re-parameterized function WP04 at 6-311G(d,p) basis set, and show nice correlation with the experimental data. Four conformers were considered for NMR chemical shift calculations. Electronic properties such as band gap, Ionization potential and electron affinities were also simulated for the first time; however, no comparison could be made with the experiment.
    Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 04/2015; 148:375. DOI:10.1016/j.saa.2015.04.018* · 2.13 Impact Factor
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    ABSTRACT: 1,4-Dihydropyridine-3,5-dicarboxylate derivatives (1-25) were synthesized in high yields via Hantzsch reaction and evaluated for their α-glucosidase inhibitory activity. Compounds 1, 2, 6-8, 11, 13-15, and 23-25 showed a potent inhibitory activity against yeast α-glucosidase with IC50 values in the range of 35.0-273.7 μM, when compared with the standard drug acarbose (IC50 = 937 ± 1.60 μM). Their structures were characterized by different spectroscopic techniques. The kinetics, selectivity, and toxicity studies on these compounds were also carried out. The kinetic studies on most active compounds 14 and 25 determined their modes of inhibition and dissociation constants Ki. Compound 14 was found to be a non-competitive inhibitor with Ki = 25.0 ± 0.06, while compound 25 was identified as a competitive inhibitor with Ki = 66.0 ± 0.07 μM. Copyright © 2015 Elsevier Masson SAS. All rights reserved.
    European Journal of Medicinal Chemistry 03/2015; 95. DOI:10.1016/j.ejmech.2015.03.018 · 3.43 Impact Factor
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    ABSTRACT: The phytochemical examination of chloroform soluble fraction (FX2) of methanolic extract of bark of Millettia ovalifolia yielded a new flavonoid; 7-(4-methoxyphenyl)-9H-furo [2,3-f]chromen-9-one (1). Compound 1 is characterized by spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR spectroscopy, and mass spectrometry. A theoretical model is also developed for obtaining geometric, electronic and spectroscopic properties of 1. The geometry optimization and harmonic vibration simulations have been carried out at B3LYP/6-31G(d,p). The vibrational spectrum of compound 1 shows nice correlation with the experimental IR spectrum, through a scaling factor of 0.9613. (1)H and (13)C NMR chemical shifts are simulated using Cramer's re-parameterized function WP04 at 6-31G(d,p) basis set, and correlate nicely with the experimental chemical shifts. Copyright © 2015 Elsevier B.V. All rights reserved.
    Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 03/2015; 146. DOI:10.1016/j.saa.2015.03.061 · 2.13 Impact Factor
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    ABSTRACT: Objective: To investigate the anticancer and antioxidant potential of methanol bark extract of Ziziphus mauritiana (Z. mauritiana), which is used by traditional healers to cure some cases of cancer in Cameroon. Methods: The methanol crude extract of Z. mauritiana has the antiproliferative activity on four cancer cell lines and its antioxidant activity. The extract was partitioned in five different solvents, and each fraction was tested. The effect of the most antiproliferative fraction on cell cycle was determined. Bio-guided fractionation was performed on the fraction with the highest antiproliferative and the highest antioxidant activities. Results: Z. mauritiana methanol extract was active on all tested cells, and showed promising antioxidant activity. All fractions except hexane fraction were active with the dichloromethane fraction being the most active and showed S and G2-M phase arrest (P<0.01) on cell cycle progression of NCI-H460 and MCF-7, respectively. Bio-guided fractionation of the dichloromethane fraction led to lupeol and betulinic acid. The greatest antioxidant activity was recorded with ethyl acetate fraction and its fractionation led to catechin and epigallocatechin. Conclusions: Overall, this study showed that Z. mauritiana barks has benefits as a chemoprevention agent cancer.
    02/2015; 5(4). DOI:10.1016/S2222-1808(14)60788-X
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    Shehzaib Siddiqui, Atia-tul-Wahab, M. Iqbal Choudhary
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    ABSTRACT: Staphylococcus aureus is a toxin producing pathogen that causes aggressive, life threatening infections. The irrational use of antimicrobial drugs in last four decades has led to the emergence of multi-drug resistant (MDR) Staphylococcus aureus infections. This is due to the ability of pathogen to alter the drug targets, either by mutation in its genome or by acquiring resistance related genes from niche. There is an increasing demand for the discovery of novel antimicrobial drugs and identification of new drug targets to control spread of MDR infections. Structural and functional characterization of hypothetical proteins from S. aureus may reveal some important drug targets. Therefore, in current study, SAR2568, a hypothetical protein from methicillin-resistant S. aureus (MRSA252) has been cloned in pET25b expression vector and transformed in E. coli DH5α cells. Transformed colonies were screened by colony PCR and sequence integrity was checked via DNA sequencing. Successfully cloned constructs were transformed in E. coli BL21 (DE3) cells, followed by induction with IPTG in minimal medium. Expressed protein was purified by ion-exchange and gel filtration chromatography techniques on FPLC system. The structure and function of the protein was predicted as DNA binding protein by using CPH Models and SVMProt, respectively. The NMR-based structural studies on this important protein are currently underway.
    5thInternational Symposium-cum-Training Course on Molecular Medicine and Drug Research (MMDR-5), International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan.; 01/2015
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    Dataset: BMC Paper
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    ABSTRACT: Benzothiazole derivatives 1-22 were synthesized from 2-aminothiophenol and all synthetic compounds were screened for in vitro antileishmanial activity. T hese compound showed different types activities against leishmania with IC50 values ranging between 18.32-81.89 µM. Compound 2 (IC50 = 18.32 ± 0.18 µM), 5 (IC50 = 19.72 ± 0.32 µM), and 3 (IC50 = 21.87 ± 0.43 µM) were found to be the most active compounds among the series when compared to the standard (Pentamidine, IC50 = 5.09 ± 0.04 µM). Compounds 7 and 11 exhibited weak activities, while compounds 5, 6, 7, 10, 11, and 16 were also found active. However, remaining compounds were found to be inactive against leishmania.
    Journal- Chemical Society of Pakistan 01/2015; 37(01). · 0.61 Impact Factor
  • ChemInform 01/2015; 46(3). DOI:10.1002/chin.201503206
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    Article: Overview
    Atta-ur-Rahman, M. Iqbal Choudhary, George Perry
    Mini Reviews in Medicinal Chemistry 01/2015; 15(1):2-3. DOI:10.2174/138955751501150224153345 · 3.19 Impact Factor

Publication Stats

4k Citations
952.34 Total Impact Points

Institutions

  • 2013–2015
    • King Abdulaziz University
      • Department of Biochemistry
      Djidda, Makkah, Saudi Arabia
  • 2006–2015
    • University of Yaoundé II
      Jaúnde, Centre, Cameroon
    • Suez Canal University
      • Department of Chemistry
      Al Ismā‘īlīyah, Al Ismā‘īlīyah, Egypt
  • 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
      • • Department of Pharmacognosy
      Kurrachee, Sindh, Pakistan
  • 2011–2014
    • King Saud University
      • Department of Chemistry
      Ar Riyāḑ, Ar Riyāḑ, Saudi Arabia
  • 2010
    • Quaid-i-Azam University
      • Department of Chemistry
      Islāmābād, Islāmābād, Pakistan
  • 2005–2010
    • University of Tuebingen
      • Institute of Physical and Theoretical Chemistry
      Tübingen, Baden-Württemberg, Germany
    • University of Yaounde I
      • Faculty of Sciences
      Yaoundé, Centre Province, Cameroon
    • University of Science Malaysia
      • School of Physics
      Nibong Tepal, Penang, Malaysia
  • 1997–2010
    • The University of Calgary
      • Department of Chemistry
      Calgary, Alberta, Canada
  • 2008
    • University of Peshawar
      • Institute of Chemical Sciences
      Peshawar, North-West Frontier Province, Pakistan
    • University of Vermont
      • Department of Chemistry
      Burlington, VT, United States
  • 2004–2008
    • Tribhuvan University
      • Institute of Forestry
      Kantipura, Central Region, Nepal
  • 2007
    • Universität Paderborn
      Paderborn, North Rhine-Westphalia, Germany
  • 2004–2005
    • University of the Philippines Diliman
      • Institute of Chemistry
      Diliman, Central Luzon, Philippines
  • 2002–2004
    • University of Dhaka
      • Department of Chemistry
      Mujib City, Dhaka, Bangladesh
    • The University of Winnipeg
      • Department of Chemistry
      Winnipeg, Manitoba, Canada
  • 1986–2004
    • Pennsylvania State University
      • Department of Chemistry
      University Park, Maryland, United States
  • 1993–1999
    • Gazi University
      • Department of Pharmacognosy
      Engüri, Ankara, Turkey
  • 1995
    • University of Washington Seattle
      Seattle, Washington, United States
    • University of Colombo
      Columbo, Western, Sri Lanka
    • Gomal University
      • Department of Chemistry
      Dera Ismāīl Khān, Khyber Pakhtunkhwa, Pakistan
    • University of Jordan
      • Department of Chemistry
      Amman, Amman, Jordan
  • 1988–1993
    • Cornell University
      Ithaca, New York, United States