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Raihan Chowdhury
Beth Israel Deaconess Medical Center, Harvard Medical School

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Chapter
Published: 28 August 2021 in Application of Ionic Liquids in Drug Delivery
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Ionic Liquids (ILs) have been a topic of interest in many scientific areas since the mid-1990s and can be classified as potential “green solvents,” especially for use in drug delivery systems (DDSs). Because of the “green” and “designer” properties of ILs, the use of ILs has escalated dramatically in pharmaceutics and medicine. Although virtually an unlimited number of ILs could be produced from diverse sources of organic and inorganic cations and anions, including IL precursors derived from biological sources, special consideration must be given for the implementation of ILs in DDSs. Herein, the focus is on the design of the ILs, rather than their implementation in DDSs, particularly the precursor selection, biocompatibility status for safety (biosafety), and potential for targeted drug delivery. It is possible to design an IL suitable for a DDS with synergistic benefits by achieving the maximum therapeutic efficacy of the drug with minimum undesirable side effects caused by the delivery systems or vehicles.

ACS Style

Raihan Chowdhury; Nurunnabi; Masahiro Goto. Design Principles for Ionic Liquids in Drug Delivery Systems. Application of Ionic Liquids in Drug Delivery 2021, 1 -12.

AMA Style

Raihan Chowdhury, Nurunnabi, Masahiro Goto. Design Principles for Ionic Liquids in Drug Delivery Systems. Application of Ionic Liquids in Drug Delivery. 2021; ():1-12.

Chicago/Turabian Style

Raihan Chowdhury; Nurunnabi; Masahiro Goto. 2021. "Design Principles for Ionic Liquids in Drug Delivery Systems." Application of Ionic Liquids in Drug Delivery , no. : 1-12.

Research article
Published: 04 August 2021 in ACS Applied Bio Materials
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Lipid-based biocompatible ionic liquids (LBILs) have attracted attention as carriers in transdermal drug delivery systems (TDDSs) because of their lipophilic character. In this study, we report the formulation of a peptide–LBIL complex microencapsulated in an oil phase as a potential carrier for the transdermal delivery of leuprolide acetate as a model hydrophilic peptide. The peptide–LBIL complexes were prepared via a water-in-oil emulsion composed of 1,2-dimyristoyl-sn-glycerol-3-ethyl-phosphatidylcholine (EDMPC), a fatty acid (stearic, oleic, and linoleic acid)-based LBIL, and cyclohexane followed by freeze-drying to remove the water and cyclohexane. Then, the peptide–LBIL complexes were nanodispersed and stabilized in isopropyl myristate (IPM) using sorbitol laurate (Span-20). Ionic-liquid-in-oil nanodispersions (IL/O-NDs) were prepared with varying weight ratios of LBILs and Span-20 as the surfactant and the cosurfactant, respectively. Keeping the overall surfactant constant at 10 wt % in IPM, a 5:5 wt % ratio of surfactant (IL) and cosurfactant (Span-20) in the IL/O-NDs significantly (p < 0.0001) increased the physiochemical stability, drug-loading capacity, and drug encapsulation efficiency. The in vitro and in vivo peptide delivery across the skin was increased significantly (p < 0.0001) using IL/O-NDs, compared with non-IL-treated groups. Of all of the LBIL-based formulations, [EDMPC][Linoleate]/O-ND was considered the most preferable for a TDDS based on the pharmacokinetic parameters. The transdermal delivery flux with [EDMPC][Linoleate]/O-ND was increased 65-fold compared with the aqueous delivery vehicle. The IL/O-NDs were able to deform the lipid and protein arrangements of the skin layers to enhance the transdermal permeation of the peptide. In vitro and in vivo cytotoxicity studies of the IL/O-NDs revealed the biocompatibility of the LBIL-based formulations. These results indicated that IL/O-NDs are promising biocompatible carriers for lipid–peptide TDDSs.

ACS Style

Shihab Uddin; Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug. ACS Applied Bio Materials 2021, 4, 6256 -6267.

AMA Style

Shihab Uddin, Rafiqul Islam, Raihan Chowdhury, Rie Wakabayashi, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug. ACS Applied Bio Materials. 2021; 4 (8):6256-6267.

Chicago/Turabian Style

Shihab Uddin; Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2021. "Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug." ACS Applied Bio Materials 4, no. 8: 6256-6267.

Communication
Published: 07 October 2020 in Chemical Communications
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This study reports a new series of lipid-based biocompatible ionic liquids consisting of long-chain phosphonium compound, 1,2-dimyristoyl-sn-glycero-3-ethyl- phosphatidylcholine, as a cation and long chain fatty acids as anions.

ACS Style

Shihab Uddin; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation. Chemical Communications 2020, 56, 13756 -13759.

AMA Style

Shihab Uddin, Raihan Chowdhury, Rie Wakabayashi, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation. Chemical Communications. 2020; 56 (89):13756-13759.

Chicago/Turabian Style

Shihab Uddin; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2020. "Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation." Chemical Communications 56, no. 89: 13756-13759.

Critical review
Published: 14 September 2020 in Green Chemistry
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This critical review highlights the recent advancements of using biocompatible ionic liquids as “green” designer solvents and/or materials to overcome the limitations caused by conventional organic solvents/materials in pharmaceutics and medicine.

ACS Style

Rahman Md Moshikur; Raihan Chowdhury; Muhammad Moniruzzaman; Masahiro Goto. Biocompatible ionic liquids and their applications in pharmaceutics. Green Chemistry 2020, 22, 8116 -8139.

AMA Style

Rahman Md Moshikur, Raihan Chowdhury, Muhammad Moniruzzaman, Masahiro Goto. Biocompatible ionic liquids and their applications in pharmaceutics. Green Chemistry. 2020; 22 (23):8116-8139.

Chicago/Turabian Style

Rahman Md Moshikur; Raihan Chowdhury; Muhammad Moniruzzaman; Masahiro Goto. 2020. "Biocompatible ionic liquids and their applications in pharmaceutics." Green Chemistry 22, no. 23: 8116-8139.

Journal article
Published: 24 April 2020 in Pharmaceutics
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The transdermal delivery of sparingly soluble drugs is challenging due to of the need for a drug carrier. In the past few decades, ionic liquid (IL)-in-oil microemulsions (IL/O MEs) have been developed as potential carriers. By focusing on biocompatibility, we report on an IL/O ME that is designed to enhance the solubility and transdermal delivery of the sparingly soluble drug, acyclovir. The prepared MEs were composed of a hydrophilic IL (choline formate, choline lactate, or choline propionate) as the non-aqueous polar phase and a surface-active IL (choline oleate) as the surfactant in combination with sorbitan laurate in a continuous oil phase. The selected ILs were all biologically active ions. Optimized pseudo ternary phase diagrams indicated the MEs formed thermodynamically stable, spherically shaped, and nano-sized (90%) with the ME compared with Dulbecco’s phosphate-buffered saline, indicates the biocompatibility of the ME. Therefore, we conclude that IL/O ME may be a promising nano-carrier for the transdermal delivery of sparingly soluble drugs.

ACS Style

Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Ionic Liquid-In-Oil Microemulsions Prepared with Biocompatible Choline Carboxylic Acids for Improving the Transdermal Delivery of a Sparingly Soluble Drug. Pharmaceutics 2020, 12, 392 .

AMA Style

Rafiqul Islam, Raihan Chowdhury, Rie Wakabayashi, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Ionic Liquid-In-Oil Microemulsions Prepared with Biocompatible Choline Carboxylic Acids for Improving the Transdermal Delivery of a Sparingly Soluble Drug. Pharmaceutics. 2020; 12 (4):392.

Chicago/Turabian Style

Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2020. "Ionic Liquid-In-Oil Microemulsions Prepared with Biocompatible Choline Carboxylic Acids for Improving the Transdermal Delivery of a Sparingly Soluble Drug." Pharmaceutics 12, no. 4: 392.

Communication
Published: 03 June 2019 in Chemical Communications
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We report a one-step emulsification and rapid freeze-drying process to develop a curcumin–ionic liquid (CCM–IL) complex that could be readily dispersed in water with a significantly enhanced solubility and half-life compared to free CCM.

ACS Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Development of a novel ionic liquid–curcumin complex to enhance its solubility, stability, and activity. Chemical Communications 2019, 55, 7737 -7740.

AMA Style

Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Development of a novel ionic liquid–curcumin complex to enhance its solubility, stability, and activity. Chemical Communications. 2019; 55 (54):7737-7740.

Chicago/Turabian Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2019. "Development of a novel ionic liquid–curcumin complex to enhance its solubility, stability, and activity." Chemical Communications 55, no. 54: 7737-7740.

Journal article
Published: 08 May 2019 in International Journal of Pharmaceutics
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In order to prevent common hypersensitivity reactions to paclitaxel injections (Taxol), we previously reported an ionic liquid-mediated paclitaxel (IL-PTX) formulation with small particle size and narrow size distribution. The preliminary work showed high PTX solubility in the IL, and the formulation demonstrated similar antitumor activity to Taxol, while inducing a smaller hypersensitivity effect in in vitro cell experiments. In this study, the stability of the IL-PTX formulation was monitored by quantitative HPLC analysis, which showed that IL-PTX was more stable at 4 °C than at room temperature. The in vivo study showed that the IL-PTX formulation could be used in a therapeutic application as a biocompatible component of a drug delivery system. To assess the in-vivo biocompatibility, IL or IL-mediated formulations were administered intravenously by maintaining physiological buffered conditions (neutral pH and isotonic salt concentration). From in vivo pharmacokinetics data, the IL-PTX formulation was found to have a similar systemic circulation time and slower elimination rate compared to cremophor EL mediated paclitaxel (CrEL-PTX). Furthermore, in vivo antitumor and hypersensitivity experiments in C57BL/6 mice revealed that IL-PTX had similar antitumor activity to CrEL-PTX, but a significantly smaller hypersensitivity effect compared with CrEL-PTX. Therefore, the IL-mediated formulation has potential to be an effective and safe drug delivery system for PTX.

ACS Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. In vivo biocompatibility, pharmacokinetics, antitumor efficacy, and hypersensitivity evaluation of ionic liquid-mediated paclitaxel formulations. International Journal of Pharmaceutics 2019, 565, 219 -226.

AMA Style

Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. In vivo biocompatibility, pharmacokinetics, antitumor efficacy, and hypersensitivity evaluation of ionic liquid-mediated paclitaxel formulations. International Journal of Pharmaceutics. 2019; 565 ():219-226.

Chicago/Turabian Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2019. "In vivo biocompatibility, pharmacokinetics, antitumor efficacy, and hypersensitivity evaluation of ionic liquid-mediated paclitaxel formulations." International Journal of Pharmaceutics 565, no. : 219-226.

Journal article
Published: 14 January 2019 in Journal of Molecular Liquids
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The technological utility of active pharmaceutical ingredients (APIs) is enormously improved when they are converted into ionic liquids (ILs). API-ILs possess better aqueous solubility and thermal stability than that of solid-state salt or crystalline drugs. However, many such API-ILs are not biocompatible or biodegradable. In the current study, we synthesized a series of IL-APIs using methotrexate (MTX), a potential anticancer prodrug, and biocompatible IL-forming cations (choline and amino acid esters). The MTX-IL moieties were characterized through 1H NMR, FTIR, p-XRD, DSC and thermogravimetric analysis. The solubility of the MTX-ILs was evaluated in simulated body fluids (phosphate-buffered saline, simulated gastric, and simulated intestinal fluids). An assessment of the in vitro antitumor activity of the MTX-ILs in a mammalian cell line (HeLa cells) was used to evaluate their cytotoxicity. The MTX-ILs showed aqueous solubility at least 5000 times higher than that of free MTX and two orders of magnitude higher compared with that of a sodium salt of MTX in both water and simulated body fluids. Importantly, a proline ethyl ester MTX prodrug showed similar solubility as the MTX sodium salt but it provided improved in vitro antitumor activity. These results clearly suggest that the newly synthesized API-ILs represent promising potential drug formulations.

ACS Style

Rahman Md Moshikur; Raihan Chowdhury; Rie Wakabayashi; Yoshiro Tahara; Muhammad Moniruzzaman; Masahiro Goto. Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation. Journal of Molecular Liquids 2019, 278, 226 -233.

AMA Style

Rahman Md Moshikur, Raihan Chowdhury, Rie Wakabayashi, Yoshiro Tahara, Muhammad Moniruzzaman, Masahiro Goto. Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation. Journal of Molecular Liquids. 2019; 278 ():226-233.

Chicago/Turabian Style

Rahman Md Moshikur; Raihan Chowdhury; Rie Wakabayashi; Yoshiro Tahara; Muhammad Moniruzzaman; Masahiro Goto. 2019. "Ionic liquids with methotrexate moieties as a potential anticancer prodrug: Synthesis, characterization and solubility evaluation." Journal of Molecular Liquids 278, no. : 226-233.

Research article
Published: 15 May 2018 in Molecular Pharmaceutics
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Paclitaxel (PTX) injection (i.e. Taxol) has been used as an effective chemotherapeutic treatment for various cancers. However, the current Taxol formulation contains Cremophor EL, which causes hypersensitivity reactions during intravenous administration and precipitation by aqueous dilution. This article reports the preliminary results on the ionic liquid (IL)-based PTX formulations developed to address the aforementioned issues. The formulations were composed of PTX/cholinium amino acid ILs/ethanol/tween-80/water. A significant enhancement in the solubility of PTX was observed with considerable correlation with the density and viscosity of the ILs, and with the side chain of the amino acids used as anions in the ILs. Moreover, the formulations were stable for up to 3 months. The driving force for the stability of the formulation was hypothesized to be the involvement of different types of interactions between the IL and PTX. In vitro cytotoxicity and anti-tumor activity of the IL-based formulations were evaluated on HeLa cells. The IL vehicles without PTX were found to be less cytotoxic than Taxol, while both the IL-based PTX formulation and Taxol exhibited similar antitumor activity. Finally, in vitro hypersensitivity reactions were evaluated on THP-1 cells and found to be significantly lower with the IL-based formulation than Taxol. This study demonstrated that specially designed ILs could provide a potentially safer alternative to Cremophor EL as an effective PTX formulation for cancer treatment giving fewer hypersensitivity reactions.

ACS Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Ionic-Liquid-Based Paclitaxel Preparation: A New Potential Formulation for Cancer Treatment. Molecular Pharmaceutics 2018, 15, 2484 -2488.

AMA Style

Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Ionic-Liquid-Based Paclitaxel Preparation: A New Potential Formulation for Cancer Treatment. Molecular Pharmaceutics. 2018; 15 (6):2484-2488.

Chicago/Turabian Style

Raihan Chowdhury; Rahman Md Moshikur; Rie Wakabayashi; Yoshiro Tahara; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2018. "Ionic-Liquid-Based Paclitaxel Preparation: A New Potential Formulation for Cancer Treatment." Molecular Pharmaceutics 15, no. 6: 2484-2488.

Journal article
Published: 08 May 2018 in International Journal of Pharmaceutics
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The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs.

ACS Style

Rahman Md Moshikur; Raihan Chowdhury; Rie Wakabayashi; Yoshiro Tahara; Muhammad Moniruzzaman; Masahiro Goto. Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids. International Journal of Pharmaceutics 2018, 546, 31 -38.

AMA Style

Rahman Md Moshikur, Raihan Chowdhury, Rie Wakabayashi, Yoshiro Tahara, Muhammad Moniruzzaman, Masahiro Goto. Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids. International Journal of Pharmaceutics. 2018; 546 (1-2):31-38.

Chicago/Turabian Style

Rahman Md Moshikur; Raihan Chowdhury; Rie Wakabayashi; Yoshiro Tahara; Muhammad Moniruzzaman; Masahiro Goto. 2018. "Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids." International Journal of Pharmaceutics 546, no. 1-2: 31-38.

Comparative study
Published: 01 January 2013 in BMC Research Notes
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Sputum smear microscopy is fast and inexpensive technique for detecting tuberculosis (TB) in high incidence areas but has low sensitivity. Physical and chemical sputum processing along with centrifugation have been found to show promise in overcoming this limitation. Our objective was to compare the sensitivity of smear microscopy obtained with smears made directly from respiratory specimens to those from concentrated specimens.

ACS Style

Mohammad Khaja Mafij Uddin; Raihan Chowdhury; Shahriar Ahmed; Toufiq Rahman; Razia Khatun; Frank Van Leth; Sayera Banu. Comparison of direct versus concentrated smear microscopy in detection of pulmonary tuberculosis. BMC Research Notes 2013, 6, 291 -291.

AMA Style

Mohammad Khaja Mafij Uddin, Raihan Chowdhury, Shahriar Ahmed, Toufiq Rahman, Razia Khatun, Frank Van Leth, Sayera Banu. Comparison of direct versus concentrated smear microscopy in detection of pulmonary tuberculosis. BMC Research Notes. 2013; 6 (1):291-291.

Chicago/Turabian Style

Mohammad Khaja Mafij Uddin; Raihan Chowdhury; Shahriar Ahmed; Toufiq Rahman; Razia Khatun; Frank Van Leth; Sayera Banu. 2013. "Comparison of direct versus concentrated smear microscopy in detection of pulmonary tuberculosis." BMC Research Notes 6, no. 1: 291-291.

Journal article
Published: 12 June 2012 in International Journal of Natural Sciences
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Tuberculosis is a global public health issue and a disease burden in Africa and Asia. Bangladesh is one of the high burden countries in Southeast Asian region. Mycobacterium tuberculosis the causative agent of tuberculosis, is a devastating bacterium because it spreads person to person, acquired multiple antibiotic resistance and most importantly has the limitation in rapid diagnosis, specially in case of extrapulmonary infection. Here we showed Real-Time PCR assay with the primers targeting IS6110 is a better method than conventional AFB microscopy for the diagnosis of extrapulmonary tuberculosis. For the comparative study 99 extrapulmonary specimens from 9 different parts of the body were collected from suspected patients. Among those only 10 samples were positive, where 50% them were scanty positive in AFB microscopy, on the other hand 33 samples were positive in Real–Time PCR assay. All samples positive in AFB microscopy were also positive in Real-Time PCR assay with an additional 23 positive. Higher percentage of positive results were found in Real-Time PCR analysis in all the samples except Percutaneous nephrostomy (PCN) fluid and Pus. The sharp differences in the result indicate the effectiveness and of the Real-Time PCR assay over the conventional AFB microscopy. High precision and accuracy make it better choice as a diagnostic method for the diagnosis of extrapulmonary tuberculosis. DOI: http://dx.doi.org/10.3329/ijns.v2i1.10880 International Journal of Natural Sciences (2012), 2(1): 26-32

ACS Style

Chowdhury; Smn Bari; Ks Islam; Agm Rakibuzzaman; S Afrin. Evaluation of Real Time PCR for the diagnosis of Extrapulmonary Tuberculosis and comparison with AFB Microscopy among Bangladeshi population. International Journal of Natural Sciences 2012, 2, 26 -32.

AMA Style

Chowdhury, Smn Bari, Ks Islam, Agm Rakibuzzaman, S Afrin. Evaluation of Real Time PCR for the diagnosis of Extrapulmonary Tuberculosis and comparison with AFB Microscopy among Bangladeshi population. International Journal of Natural Sciences. 2012; 2 (1):26-32.

Chicago/Turabian Style

Chowdhury; Smn Bari; Ks Islam; Agm Rakibuzzaman; S Afrin. 2012. "Evaluation of Real Time PCR for the diagnosis of Extrapulmonary Tuberculosis and comparison with AFB Microscopy among Bangladeshi population." International Journal of Natural Sciences 2, no. 1: 26-32.