Publications by authors named "Zulfiqar Ali Khan"

18 Publications

  • Page 1 of 1

Quinazolinones as Competitive Inhibitors of Carbonic Anhydrase-II (Human and Bovine): Synthesis, , Selectivity, and Kinetics Studies.

Front Chem 2020 1;8:598095. Epub 2020 Dec 1.

Natural and Medical Sciences Research Center, University of Nizwa, Nizwa, Oman.

Carbonic anhydrase-II (CA-II) is associated with glaucoma, malignant brain tumors, and renal, gastric, and pancreatic carcinomas and is mainly involved in the regulation of the bicarbonate concentration in the eyes. CA-II inhibitors can be used to reduce the intraocular pressure usually associated with glaucoma. In search of potent CA-II inhibitors, a series of quinazolinones derivatives () were synthesized and characterized by IR and NMR spectroscopy. The inhibitory potential of all the compounds was evaluated against bovine carbonic anhydrase-II (CA-II) and human carbonic anhydrase-II (CA-II), and compounds displayed moderate to significant inhibition with IC values of 8.9-67.3 and 14.0-59.6 μM, respectively. A preliminary structure-activity relationship suggested that the presence of a nitro group on the phenyl ring at R position contributes significantly to the overall activity. Kinetics studies of the most active inhibitor, , against both CA-II and CA-II were performed to investigate the mode of inhibition and to determine the inhibition constants (Ki). According to the kinetics results, is a competitive inhibitor of CA-II and CA-II with Ki values of 13.0 ± 0.013 and 14.25 ± 0.017 μM, respectively. However, the selectivity index reflects that the compounds and are more selective for CA-II. The binding mode of these compounds within the active sites of CA-II and CA-II was investigated by structure-based molecular docking. The docking results are in complete agreement with the experimental findings.
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http://dx.doi.org/10.3389/fchem.2020.598095DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7736042PMC
December 2020

Synthesis, molecular docking and anti-diabetic studies of novel benzimidazole-pyrazoline hybrid molecules.

Pak J Pharm Sci 2020 Mar;33(2(Supplementary)):847-854

Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia/Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.

Pyrazoline and benzimidazoles derivatives have been widely studied due to their potential applications in the medicinal field. In this research project, we have hybridized these two heterocyclic systems in the same molecule. A new series of compounds, 2-((3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)methyl)-1H-benzo[d]imidazole (5a-i) were synthesized through a multistep reaction. In the first step, chalcones 3a-i were prepared by coupling of various acetophenones and benzaldehydes under alkaline conditions. These chalcones were cyclized with hydrazine hydrate to form a series of pyrazolines which were finally coupled with 2-chloromethyl-1H-benzimidazole to get a new series of titled hybrid molecules. The structures of these compounds were elucidated by spectral (1H NMR and 13C NMR) analysis. The anti-diabetic potential of these compounds was studied by screening them for their α-glucosidase inhibition activity. The SAR was established through molecular docking analysis. Compound 5d appeared as effective inhibitor with IC = 50.06μM as compared to reference drug (acarbose) having IC = 58.8μM.
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March 2020

Synthesis, evaluation of thymidine phosphorylase and angiogenic inhibitory potential of ciprofloxacin analogues: Repositioning of ciprofloxacin from antibiotic to future anticancer drugs.

Bioorg Chem 2020 07 22;100:103876. Epub 2020 Apr 22.

Natural and Medical Sciences Research Center, University of Nizwa, Nizwa 611, Oman.

Over expression of thymidine phosphorylase (TP) in various human tumors compared to normal healthy tissue is associated with progression of cancer and proliferation. The 2-deoxy-d-ribose is the final product of thymidine phosphorylase (TP) catalyzed reaction. Both TP and 2-deoxy-d-ribose are known to promote unwanted angiogenesis in cancerous cells. Discovery of potent inhibitors of thymidine phosphorylase (TP) can offer appropriate approach in cancer treatment. A series of ciprofloxacin 2, 3a-3c, 4a-4d, 5a-5b, 6 and 7 has been synthesized and characterized using spectroscopic techniques. Afterwards, inhibitory potential of synthesized ciprofloxacin 2, 3a-3c, 4a-4d, 5a-5b, 6 and 7 against thymidine phosphorylase enzyme was assessed. Out of these twelve analogs of ciprofloxacin nine analogues 3a-3c, 4a-4c, 5a-5b and 6 showed good inhibitory activity against thymidine phosphorylase. Inhibitory activity as presented by their IC values was found in the range of 39.71 ± 1.13 to 161.89 ± 0.95 μM. The 7-deazaxanthine was used as a standard inhibitor with IC = 37.82 ± 0.93 μM. Furthermore, the chick chorionic allantoic membrane (CAM) assay was used to investigate anti-angiogenic activity of the most active ciprofloxacin-based inhibitor 3b. To enlighten the important binding interactions of ciprofloxacin derivatives with target enzyme, the structure activity relationship and molecular docking studies of chosen ciprofloxacin analogues was discussed. Docking studies revealed key π-π stacking, π-cation and hydrogen bonding interactions of ciprofloxacin analogues with active site residues of thymidine phosphorylase enzyme.
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http://dx.doi.org/10.1016/j.bioorg.2020.103876DOI Listing
July 2020

Design and syntheses of 7-nitro-2-aryl-4-benzo[][1,3]oxazin-4-ones as potent anticancer and antioxidant agents.

J Mol Struct 2020 Aug 13;1214:128252. Epub 2020 Apr 13.

Interdisciplinary Research Center in Biomedical Materials, COMSATS University Islamabad, Lahore Campus, Lahore, 54000, Pakistan.

A group of new nitro substituted benzoxazinones () were synthesized from easily available 4-nitroanthranilic acid. All the synthesized compounds were characterized by FT-IR, H NMR, C NMR, mass spectrometry and elemental analysis. Anti-proliferative and pro-apoptotic potential of all the synthesized compounds () was evaluated by MTT and Hoechst 33258 staining assay respectively whereas their antioxidant properties were determined via DPPH free radical scavenging assay. The most active compounds (, and ) showed significant cytotoxic potential against HeLa cells with an inhibition of cell viability that ranged between 28.54 and 44.67% ( < 0.001). Albeit statistically different, the anti-proliferative effect of was in close match with that of the reference drug doxorubicin. Likewise, the test compounds showed profound pro-apoptotic potential with an apoptotic index that ranged between 52.86 and 75.61%. Besides, the docking studies revealed a higher efficiency for compounds ( and ) owing to their better affinity and inhibition constant (K = 4.397 and 3.713 nmol) respectively. The antioxidant potential of synthesized benzoxazinones () was in close agreement with the experimental anticancer results with a percent inhibition from 34.45 to 85.93% as compared to standard (90.56%).
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http://dx.doi.org/10.1016/j.molstruc.2020.128252DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7153534PMC
August 2020

5-Endo-dig cyclizations in organic syntheses.

Mol Divers 2020 Feb 5;24(1):295-317. Epub 2019 Mar 5.

Department of Chemistry, Faculty of Physical Sciences, Government College University, Faisalabad, 38000, Pakistan.

The favorability of ring closure reactions as per Baldwin rules has gained immense importance recently. This is evident from the current literature such as research articles, reviews, and books that have been published in this area. This review covers the recent applications of 5-endo-dig cyclization in organic synthesis focusing in the last two decades. A variety of 5-membered heterocycles as well as carbocycles could be synthesized via 5-endo-dig cyclization reactions. The important applications of 5-endo-dig cyclization in organic synthesis covering different aspects have been summarized in this review.
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http://dx.doi.org/10.1007/s11030-019-09930-xDOI Listing
February 2020

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs.

Bioorg Chem 2019 04 4;85:209-220. Epub 2019 Jan 4.

Department of Physicochemical Drug Analysis, Faculty of Pharmacy, Jagiellonian University Medical College, 30-688 Cracow, Medyczna 9, Poland.

Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a-3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a-3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a-4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b-4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11-163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.
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http://dx.doi.org/10.1016/j.bioorg.2019.01.005DOI Listing
April 2019

Technetium-99m radiolabeling and biological study of epirubicin for in vivo imaging of multi-drug-resistant Staphylococcus aureus infections via single photon emission computed tomography.

Chem Biol Drug Des 2019 02 31;93(2):154-162. Epub 2018 Oct 31.

Department of Chemistry, Government College University, Faisalabad, Pakistan.

The development of functional imaging is a promising strategy for diagnosis and treatment of infectious and cancerous diseases. In this study, epirubicin was developed as a [ Tc]-labeled radiopharmaceutical for the imaging of multi-drug-resistant Staphylococcus aureus infections. The labeling was carried out using sodium pertechnetate (Na TcO ; ~370 MBq). The other parameters such as amount of ligand, reducing agent (SnCl .2H O), and pH were optimized. The highest labeling yield ≥96.98% was achieved when 0.3 mg epirubicin, 13 μg SnCl .2H O, and ~370 MBq Na TcO were incubated at pH 7 for 15 min in the presence of ascorbic acid at room temperature. Radiochemical purity, stability, charge, and glomerular filtration rate were studied to evaluate the biological compatibility for in vivo administration. Biodistribution investigations showed radiotracer uptake (13.89 ± 1.56% ID/gm organ) by liver and 7.79 ± 0.38% ID/gm organ by kidneys at 30 min post-injection which promisingly wash out at 24 hr post-injection. Scintigraphy study showed selective uptake in S. aureus-infected tissues in contrast to turpentine oil-induced inflamed tissues. Target-to-non-target ratio (6.7 ± 0.05) was calculated at 1 hr post-injection using SPECT gamma camera. The results of this study reveal that the [ Tc]-epirubicin can be a choice of imaging and monitoring the treatment process of multi-drug resistant S. aureus bacterial infections.
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http://dx.doi.org/10.1111/cbdd.13393DOI Listing
February 2019

Synthetic approaches toward stilbenes and their related structures.

Mol Divers 2017 May 21;21(2):483-509. Epub 2017 Apr 21.

Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, 22060, Pakistan.

Compounds belonging to the stilbene family have gained remarkable significance in pharmaceutical as well as material chemistry. The current review covers the various synthetic approaches for the syntheses of stilbene scaffold and related structures over last 30 years. In addition, this review also highlights the role of stilbene intermediates used in the synthesis of important molecules with diverse applications in the field of pharmaceutics and material science.
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http://dx.doi.org/10.1007/s11030-017-9736-9DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7089417PMC
May 2017

Compositional difference in antioxidant and antibacterial activity of all parts of the Carica papaya using different solvents.

Chem Cent J 2016 3;10. Epub 2016 Feb 3.

Department of Crop Science, Faculty of Agriculture, UPM, 43400 Serdang, Selangor Malaysia.

Background: Carica papaya is a well known medicinal plant used in the West and Asian countries to cope several diseases. Patients were advised to eat papaya fruit frequently during dengue fever epidemic in Pakistan by physicians. This study was conducted to establish Polyphenols, flavonoids and antioxidant potential profile of extracts of all major parts of the C. papaya with seven major solvents i.e. water, ethanol, methanol, n-butanol, dichloromethane, ethyl acetate, and n-hexane.

Results: TPC, TFC, antioxidant and antibacterial potential were determined using different aqueous and organic solvents in addition to the determination of trace element in leaves, pulp and peel of C. papaya. Total soluble phenolics and flavonoids were found in promising quantity (≈66 mg GAE/g) especially in case of methanol and ethanol extracts. Antioxidant activity using DPPH free radical scavenging assay indicated leaves, bark, roots and pulp extracts showed >75.0 % scavenging potential while leaves and pulp showed 84.9 and 80.9 % inhibition of peroxidation, respectively. Reducing power assay showed leaves, pulp and roots extracts active to reduce Fe(3+) to Fe(2+) ions. The antibacterial study showed pulp extract is the best to cope infectious action of bacteria.

Conclusion: This study was conducted to test the medicinal profile of all parts of C. papaya by extracting secondary metabolites with organic and aqueous solvents. Ethanol and methanol both were found to be the best solvents of choice to extract natural products to get maximum medicinal benefits and could be used to medicinal formulation against different infectious diseases.Graphical abstractMedicinal evaluation of different parts of C. papaya.
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http://dx.doi.org/10.1186/s13065-016-0149-0DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4741006PMC
February 2016

Synthesis, thymidine phosphorylase inhibition and molecular modeling studies of 1,3,4-oxadiazole-2-thione derivatives.

Bioorg Chem 2015 Jun 20;60:37-41. Epub 2015 Apr 20.

Hussain Ibrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

Thymidine phosphorylase (TP) inhibitors have attracted great attention due to their ability to suppress the tumors formation. In our ongoing research, a series of 1,3,4-oxadiazole-2-thione (1-12) has been synthesized under simple reaction conditions in good to excellent yields (86-98%) and their TP inhibition potential has also been evaluated. The majority of synthesized compounds showed moderate thymidine phosphorylase inhibitory activity with IC50 values ranging from 38.24±1.28 to 258.43±0.43μM, and 7-deazaxanthine (7DX) was used as a reference compound (IC50 38.68±4.42). The TP activity was very much dependent on the C-5 substituents; among this series the compound 6 bearing 4-hydroxyphenyl group was found to be the most active with IC50 38.24±1.28μM. Molecular docking studies revealed their binding mode.
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http://dx.doi.org/10.1016/j.bioorg.2015.04.003DOI Listing
June 2015

Antioxidant and antibacterial activities of Hibiscus Rosa-sinensis Linn flower extracts.

Pak J Pharm Sci 2014 May;27(3):469-74

Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore, Pakistan.

Antioxidant and antibacterial potential of different solvent extracts of locally grown Hibiscus rosa-sinensis Linn was evaluated. The antioxidant activity was assessed by estimation of total flavonoids contents, total phenolic contents, DPPH free radical scavenging activity and percentage inhibition of linoleic acid oxidation capacity. Agar disc diffusion method was used to assess antibacterial potential of crude extract of H. rosa-sinensis. The yield of the crude extracts (23.21 ± 3.67 and 18.36 ± 2.98% in 80% methanol and ethanol solvents was calculated, respectively. Methanol and ethanol extract of H. rosa-sinensis showed total phenolics 61.45 ± 3.23 and 59.31 ± 4.31 mg/100g as gallic acid equivalent, total flavonoids 53.28 ± 1.93 and 32.25±1.21 mg/100g as catechine equivalent, DPPH free radical scavenging activity 75.46±4.67 and 64.98 ± 2.11% and inhibition of linoleic acid oxidation potential 75.8 ±3.22 and 61.6 ± 2.01% respectively, was measured. Antibacterial study against three human pathogens such as staphlococus sp. Bacillus sp. and Escherichia coli showed growth inhibitory effect in the range of 12.75 ± 1.17 to 16.75 ± 2.10 mm. These results showed H. rosa-sinensis indigenous to Kallar Kahar and its allied areas bear promising medicinal values and could be used for developing herbal medicines to target oxidative stress and infectious diseases.
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May 2014

Design and Synthesis of New Dual Binding Site Cholinesterase Inhibitors: Inhibition Studies with Docking.

Lett Drug Des Discov 2014 Mar;11(3):331-338

Department of Allied Sciences and Chemical Pathology, University of Health Sciences, Lahore, 54600, Pakistan.

Cholinesterases (ChEs) play a vital role in the regulation of cholinergic transmission. The inhibition of ChEs is considered to be involved in increasing acetylcholine level in the brain and thus has been implicated in the treatment of Alzheimer's disease. We have designed and synthesized a series of novel indole derivatives and screened them for inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Most of the tested compounds exhibited inhibitory activity against AChE and BChE. Among them and showed the highest AChE inhibitory activity with IC 91.21±0.06 and 68.52±0.04 μM, respectively. However compound exhibited the highest inhibitory activity against BChE (IC 55.21±0.12 μM).
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http://dx.doi.org/10.2174/15701808113106660078DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3977535PMC
March 2014

Synthesis and biological evaluation of novel oxadiazole derivatives: a new class of thymidine phosphorylase inhibitors as potential anti-tumor agents.

Bioorg Med Chem 2014 Feb 30;22(3):1008-15. Epub 2013 Dec 30.

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.

Based on the fact that the thymidine phosphorylase inhibitors are considered potential anti-tumor agents, a range of novel oxadiazole derivatives 3a-3u was designed and synthesized by a simple and facile synthetic route. The biological assay revealed that majority of compounds displayed modest inhibitory activity against thymidine phosphorylase at low micromolar concentrations (IC50 173.23±3.04 to 14.40±2.45μM). In the current study the most active compounds were 3h and 3q with IC50 values 14.40±2.45 and 17.60±1.07μM, respectively. Molecular docking studies were performed on the most active compounds (3h, 3k, 3o-3q) to show their binding mode.
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http://dx.doi.org/10.1016/j.bmc.2013.12.043DOI Listing
February 2014

Novel indium-111 labeled gastrin peptide analogues (MG-CL1-4): synthesis and quality control.

Pak J Pharm Sci 2013 Mar;26(2):299-305

Department of Chemistry, Government College University, Faisalabad, Pakistan.

Radiolabeled neuropeptides are widely investigated to diagnose and therapy of tumors. These peptides get internalization after binding with particular receptors at the surface of cells and finally move to lysosome. Internalization into tumor cells helps in mapping the infected site. Minigastrin peptide analogues (MG-CL1-4) were synthesised and labeled with 111-In radioisotope under different sets of conditions for imaging CCk-2 receptor bearing tumors. Different parameters such as temperature (80-100°C), pH (4-12), incubation time (5-30 minutes) and dilution effect were investigated to get the maximum labeling yield and stability. The results indicated that MG-CL1-4 is successfully labeled with indium-111 at pH 4.5 with heating at 98°C for 15 minute. At these conditions i.e. heating, pH and incubation minimum oxidized and maximum labeling yield, more than 94 %, was obtained. The labeling stability was studied by incubating the radiolabeled complex for predefined time points in PBSA and blood serum. Results show that more than 90% radiolabeled MG-CL1-4 remained intact.
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March 2013

Synthesis of indene derivatives via electrophilic cyclization.

Org Lett 2009 Jan;11(1):229-31

School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK.

3-Iodo-1H-indene derivatives are synthesized by iodonium-promoted 5-endo-dig carbocyclization of 2-substituted ethynylmalonates. Various 2-substituted ethynylmalonates bearing aryl-, alkyl- and ether-protected propargyl alcohols were successfully converted to cyclized products. Their use in subsequent reactions as substrate and catalyst was investigated.
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http://dx.doi.org/10.1021/ol8024956DOI Listing
January 2009

An expeditious and environmentally friendly synthesis of 3-substituted isocoumarins using microwave irradiation.

Nat Prod Res 2008 ;22(13):1120-7

HEJ Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Pakistan.

A microwave-assisted, environmentally friendly, high-yielding, time-saving synthesis of medicinally important 3-substituted isocoumarins was carried out in a single step by direct condensation of homophthalic acid with aryol and acyl chlorides under solvent-free conditions without any solid support. The synthesised isocoumarins were structurally characterised by microanalysis, 1H NMR, EI, IR and UV.
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http://dx.doi.org/10.1080/14786410601082318DOI Listing
March 2009

In vitro leishmanicidal activity of 3-substituted isocoumarins: synthesis and structure activity relationship.

Med Chem 2008 Mar;4(2):163-9

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi-75270, Pakistan.

Twenty-five 3-substituted isocoumarins were synthesized using cutting edge microwave-assisted technology in high yields. The syntheses of different isocoumarins were carried out in a single step by the direct condensation of homophthalic acid with aryol and acyl chlorides under the solvent-free conditions without any solid support. The structures of all the synthesized compounds were characterized using different spectroscopic techniques including UV, IR, (1)HNMR and EIMS and purity was confirmed by CHN analysis. All the synthesized compounds were tested for in vitro leishmanicidal activity. Compounds 3a, 3b, 3g, 3l, 3m, 3r, 3t, 3w, 3x, and 3y displayed potential in vitro leishmanicidal activity with IC(50) values in the range of 0.56-84.38 microg/ml, whereas standard inhibitors amphotericine B have IC(50) = 0.24 microg/ml. The compounds 3b, 3g, 3m, 3t, 3w, 3x, and 3y having IC(50) values 27.86, 28.88, 36.49, 34.37, 28.68, 0.89 and 0.56 microg/ml, respectively, were most active among the present series while remaining others were found less active. The compound 3x and 3y can act as potential lead molecules for further development of isocoumarin-based new drugs for the treatment of leishmaniasis.
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http://dx.doi.org/10.2174/157340608783789130DOI Listing
March 2008

Small bowel volvulus resulting in infarction due to an anterior gastropexy band.

JSLS 2002 Jan-Mar;6(1):77-9

Department of Surgery, Luton and Dunstable Hospital, UK.

Volvulus of the small bowel, although rare, carries a high risk of strangulation and ischemic necrosis. It is usually caused by the rotation of a loop of small intestine around an adhesion band or stoma. We present a case of an anterior gastropexy band, giving rise to a small bowel volvulus, necessitating resection due to infarction. This band resulted from separation of the most distal anterior gastropexy suture from the anterior abdominal wall. The distensible nature of the stomach and its resultant postprandial gain in weight produced tremendous shearing forces on the gastropexy sutures, and, as our case demonstrates, a greater number of gastropexy sutures does not protect against this complication.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3043390PMC
October 2002