Rituraj Konwar

Academy of Scientific and Innovative Research, New Dilli, NCT, India

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Publications (49)111.3 Total impact

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    ABSTRACT: A series of novel γ-(triazolyl ethylidene)butenolides (4-23) were prepared from commercially available l-ascorbic acid in good yields. These butenolides on reaction with ethanolic ammonia/amines led to formation of respective 5-hydroxy pyrrolinones (24-33). The two of these pyrrolinones on dehydration with p-toluenesulfonic acid, were transformed into γ-(triazolyl ethylidene)pyrrolinones (34, 35). Among all the newly synthesized hybrid molecules tested for anticancer activity in vitro, compounds 24, 25, 26, 27, 28, 30 and 32 showed significant activity against MCF-7, MDA-MB-231, PC-3 or U-937 cells. In particular compound 25 (IC50 = 11.3 μM) exhibited most potent activity against breast cancer cells and preliminary studies revealed that potency of this compound is due to ROS generation, subsequent activation of p38, leading to apoptosis and inhibition of cancer cells.
    European journal of medicinal chemistry. 05/2014; 82C:106-119.
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    ABSTRACT: Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20μM concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300mg/kg dose in Swiss-albino mice.
    Bioorganic & medicinal chemistry 01/2014; · 2.82 Impact Factor
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    ABSTRACT: Synthesis and bioevaluation of a novel γ-(triazolyl ethylidene)butenolides and consequent pyrrolinones is reported. In which, compound 25 showed potent activity (IC50 = 11.3 μM) against MDA-MB-231 cells in vitro.
    European Journal of Medicinal Chemistry. 01/2014; 82:106–119.
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    ABSTRACT: An attempt has been made to use curcumin (CUR) in combination with Etoposide (ETP) by encapsulating in nanoemulsion, as two tier approach i.e., to evaluate improvement in efficacy of ETP on prostate cancer cells (PC3 and DU145) and to assess their effect on cross-talk between osteoblast and tumor cells leading to metastatic cascade in bones. Nanoemulsion was developed and evaluated for size, charge, in-vitro drug release and anticancer activity, effect on cross talk between osteoblast and prostate cancer cells and pharmacokinetics in rats. The entrapment efficiency of both ETP and CUR in nanoemulsion was more than 98% while the globule size was less than 150 nm with zeta potential –29.8 mV. The percent inhibition in case of ETP and ETP: CUR (1:3 w/w) was 55.92 ± 1.2 and 41.13 ± 2.4% (at 5 μ M) respectively when tested in PC3 cells. DU-145 seemed to be less responsive in comparison to PC3 cells both in respect of ETP and their mixture (ETP + CUR). Our data shows that CUR and ETP after encapsulation in nanoemulsion (F5) were effectively delivered intracellularly in PC3 cells and the cytotoxicity of F5 was enhanced by 1.5 fold as compared to ETP + CUR at 5 μ M concentration. It has also been observed that mice calvarial osteoblasts cultured and incubated with PC-3 and DU-145 cells conditioned media induces inhibition of osteoblast differentiation event. While this inhibition was significantly reversed by F5 at 5 μ M concentration over other treated groups, the pharmacokinetic profile of both ETP and CUR was also significantly improved when administered in nanoemulsion.
    Journal of Biomedical Nanotechnology 01/2014; 10(11):3381-3391. · 5.26 Impact Factor
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    ABSTRACT: Background Free copper in Wilson disease (WD) is toxic and may reduce antioxidant, increase oxidative stress marker and thereby cytokine release and excitotoxic injury, but there is paucity of studies in humans. We report oxidative stress markers, cytokines and glutamate in neurologic WD and correlate these with their clinical severity, laboratory findings and extent of Magnetic resonance imaging (MRI) changes. Methods 29 patients with neurologic WD and 9 asymptomatic WD siblings were included and their clinical, treatment history, disease severity, biochemical findings and MRI changes were noted. Glutathione (GSH), total antioxidant capacity (TAC) and malonodialdehyde (MDA) were measured by spectrophotometer, cytokines by cytokine bead array and glutamate by the fluorometer. Results In WD patients, the glutathione (Mean ± SEM, 2.20 ± 0.06Vs2.73 ± 0.04 mg/dl, P < 0.001) and TAC (1.70 ± 0.03 Vs.2.29 ± 0.02 Trolox_Eq_mmol/L, P < 0.001) were reduced, and MDA and glutamate (23.93 ± 0.54Vs. 19.96 ± 0.27 μmol/l; P < 0.001) were increased (4.7 ± 0.11Vs. 3.03 ± 0.52 nmol/ml, P < 0.001) compared to controls. The serum IL6 {median (IQRs), 9.42(10.92) Vs. 5.2(5.34) pg/ml; P = 0.001}, IL8 {12.37(10.92) Vs. 5.63(5.52) pg/ml; P < 0.001}, IL10 {8.33(8.3) Vs. 2.05(1.37) pg/ml; P = 0.001} and TNFα {6.14(8.95) Vs. 3.61(3.58) pg/ml; P < 0.001} were also increased in WD patients compared to controls. These changes were more marked in the neurologic WD compared to asymptomatic WD and in the untreated compared to treated patients. TAC correlated with duration of illness, serum free copper, 24 hour urinary copper and serum ceruloplasmin, and glutamate with MDA, TNFα, ceruloplasmin and 24-hour urinary copper. Conclusions In WD patients, antioxidants are reduced and MDA, cytokines and glutamate are increased which are more marked in symptomatic neurologic WD than asymptomatic patients.
    Journal of Neuroimmunology. 01/2014;
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    ABSTRACT: Two series of new benzoxazepines substituted with different alkyl amino ethyl chains were synthesized comprising synthetic steps of inter and intramolecular Mitsunobu reaction, lithium aluminium hydride (LAH) reduction, debenzylation, bimolecular nucleophilic substitution (SN2) reaction. The present study investigates the effect of a tyrosine-based benzoxazepine derivative in human breast cancer cells MCF-7 and MDA-MB-231 and in breast cancer animal model. The anti-proliferative effect of 15a on MCF-7 cells was associated with G1 cell-cycle arrest. This G1 growth arrest was followed by apoptosis as 15a dose dependently increased phosphatidylserine exposure, PARP cleavage and DNA fragmentation that are hallmarks of apoptotic cell death. Interestingly, 15a activated components of both intrinsic and extrinsic pathways of apoptosis characterized by activation of caspase-8 and -9, mitochondrial membrane depolarization and increase in Bax/Bcl2 ratio. However, use of selective caspase inhibitors revealed that the caspase-8-dependent pathway is the major contributor to 15a-induced apoptosis. Compound 15a also significantly reduced the growth of MCF-7 xenograft tumors in athymic nude mice. Together, 15a could serve as a base for the development of a new group of effective breast cancer therapeutics.
    Bioorganic & medicinal chemistry letters 10/2013; · 2.65 Impact Factor
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    PLoS ONE 07/2013; · 3.73 Impact Factor
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    ABSTRACT: Inhibition of epidermal growth factor receptor (EGFR) signaling is considered to be a promising treatment strategy for estrogen receptor (ER)-negative breast tumors. We have investigated here the anti-breast cancer properties of a novel anti-proliferative benzopyran compound namely, 2-[piperidinoethoxyphenyl]-3-phenyl-2H-benzo(b)pyran (CDRI-85/287) in ER- negative and EGFR- overexpressing breast cancer cells. The benzopyran compound selectively inhibited the EGF-induced growth of MDA-MB 231 cells and ER-negative primary breast cancer cell culture. The compound significantly reduced tumor growth in xenograft of MDA-MB 231 cells in nude mice. The compound displayed better binding affinity for EGFR than inhibitor AG1478 as demonstrated by molecular docking studies. CDRI-85/287 significantly inhibited the activation of EGFR and downstream effectors MEK/Erk and PI-3-K/Akt. Subsequent inhibition of AP-1 promoter activity resulted in decreased transcription activation and expression of c-fos and c-jun. Dephosphorylation of downstream effectors FOXO-3a and NF-κB led to increased expression of p27 and decreased expression of cyclin D1 which was responsible for decreased phosphorylation of Rb and prevented the transcription of E2F- dependent genes involved in cell cycle progression from G1/S phase. The compound induced apoptosis via mitochondrial pathway and it also inhibited EGF-induced invasion of MDA-MB 231 cells as evidenced by decreased activity of MMP-9 and expression of CTGF. These results indicate that benzopyran compound CDRI-85/287 could constitute a powerful new chemotherapeutic agent against ER-negative and EGFR over-expressing breast tumors.
    PLoS ONE 06/2013; · 3.73 Impact Factor
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    ABSTRACT: Gemcitabine (dFdC) mediated cancer treatment faces obstacles, due to its high hydrophilicity. A valuable strategy was executed by synthesizing lipophilic fatty acid derivative of dFdC i.e., 4-(N)-stearoyl gemcitabine (C18dFdC), built-in into polymeric poly-lactic-co-glycolic acid nanoparticles (PLGA NPs) and compared with that of parent drug. Encapsulation of derivative within NPs was higher (68.24 +/- 3.64%) than dFdC and showed comparatively sustained drug release (19.87 +/- 1.73% within 12 hours), with a proof of increased biological half life. The cytotoxicity and flow cytometric analysis displayed enhanced MCF-7 cell inhibition by C18dFdC-NPs with higher uptake compared to dFdC-NPs. Interestingly, like gemcitabine, C18dFdC-NPs did not induce appreciable differences in blood parameters and in vivo tissue toxicity study demonstrating safe use of derivative at 40 mg/kg dose. In conclusion, the preclinical data obtained in vitro and in vivo demonstrate the C18dFdC-nanocarrier as an advantageous and promising delivery system for cancer treatment along with the potential to improve the clinical outcome of gemcitabine chemotherapy.
    Journal of Biomedical Nanotechnology 05/2013; 9(5):915-25. · 5.26 Impact Factor
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    ABSTRACT: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.
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    ABSTRACT: Combretastatin A4 analogues were synthesized on steroidal framework from gallic acid with a possibility of anti-breast cancer agents. Twenty two analogues were synthesized and evaluated for cytotoxicity against human breast cancer cell lines (MCF-7 & MDA-MB 231). The best analogue 22 showed potent antitubulin effect. Docking experiments also supported strong binding affinity of 22 to microtubule polymerase. In cell cycle analysis, 22 induced apoptosis in MCF-7 cells significantly. It was found to be non-toxic up to 300mg/kg dose in Swiss albino mice in acute oral toxicity.
    The Journal of steroid biochemistry and molecular biology 02/2013; · 3.98 Impact Factor
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    ABSTRACT: Lipophilic chalcones and their conformationally restricted analogues were synthesized and evaluated for their antitubercular efficacy against Mycobacterium tuberculosis H37Rv strain. Compounds 16, 24, 25a and 25c were found to be active MIC at 60, 30, 3.5 and 7.5μg-mL(-1). In vitro cytotoxicity of compounds 16, 24, 25a, 25c and 26 in non-cancerous human epithelial kidney cell line (HEK-293) showed that most active compound 25a was approximately 2.85 times selective towards tubercular versus healthy cells whereas compound 24 was found to be 16 times selective.
    Bioorganic & medicinal chemistry letters 01/2013; · 2.65 Impact Factor
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    ABSTRACT: TGF-β1 is a multi-functional cytokine that plays an important role in breast carcinogenesis. Critical role of TGF-β1 signaling in breast cancer progression is well documented. Some TGF-β1 polymorphisms influence its expression; however, their impact on breast cancer risk is not clear. We analyzed 1222 samples in a candidate gene-based genetic association study on two distantly located and ethnically divergent case-control groups of Indian women, followed by a population-based genetic epidemiology study analyzing these polymorphisms in other Indian populations. The c.29C>T (Pro10Leu, rs1982073 or rs1800470) and c.74G>C (Arg25Pro, rs1800471) polymorphisms in the TGF-β1 gene were analyzed using direct DNA sequencing, and peripheral level of TGF-β1 were measured by ELISA. c.29C>T substitution increased breast cancer risk, irrespective of ethnicity and menopausal status. On the other hand, c.74G>C substitution reduced breast cancer risk significantly in the north Indian group (p = 0.0005) and only in the pre-menopausal women. The protective effect of c.74G>C polymorphism may be ethnicity-specific, as no association was seen in south Indian group. The polymorphic status of c.29C>T was comparable among Indo-Europeans, Dravidians, and Tibeto-Burmans. Interestingly, we found that Tibeto-Burmans lack polymorphism at c.74G>C locus as true for the Chinese populations. However, the Brahmins of Nepal (Indo-Europeans) showed polymorphism in 2.08% of alleles. Mean TGF-β1 was significantly elevated in patients in comparison to controls (p<0.001). c.29C>T and c.74G>C polymorphisms in the TGF-β1 gene significantly affect breast cancer risk, which correlates with elevated TGF-β1 level in the patients. The c.29C>T locus is polymorphic across ethnically different populations, but c.74G>C locus is monomorphic in Tibeto-Burmans and polymorphic in other Indian populations.
    PLoS ONE 01/2013; 8(10):e75979. · 3.73 Impact Factor
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    ABSTRACT: a b s t r a c t Lipophilic chalcones and their conformationally restricted analogues were synthesized and evaluated for their antitubercular efficacy against Mycobacterium tuberculosis H37Rv strain. Compounds 16, 24, 25a and 25c were found to be active MIC at 60, 30, 3.5 and 7.5 lg-mL À1 . In vitro cytotoxicity of compounds 16, 24, 25a, 25c and 26 in non-cancerous human epithelial kidney cell line (HEK-293) showed that most active compound 25a was approximately 2.85 times selective towards tubercular versus healthy cells whereas compound 24 was found to be 16 times selective. Tuberculosis (TB) is a global health priority not only due to its morbidity and mortality but also due to its high contagious nat-ure. 1–4 In 2010, 8.8 million people fell ill with TB and 1.4 million were died of it. 5 Thus, it is second largest killer worldwide by a sin-gle infectious disease. TB becomes fiercer in combination with HIV or cancer. Even our combination therapy of PRISE is not sufficient to tackle the situation. 6–8 Poor management of chemotherapy has emerged drug resistance. The highly lipophilic cell wall of Mycobacterium is responsible for its virulence to some extent. 9 Streptomycin (1), rifampicin (2), rifapentine (3), isoniazide (4), ethionamide (5) and ethambutol (6) are some potential drugs which are being used for tuberculosis treatment (Fig. 1). However, drug resistance is a major drawback of these agents. Therefore, there is an urgent need to explore new antitubercular agents. Ironically, the low number of potential new chemical enti-ties is a worrying situation at present. Considering the severity of the problem, WHO has prepared a strategic plan in Berlin declara-tion 2007 to stop TB globally. In the recent past, several coumarin derivatives have been re-ported to exhibit antimycobacterial activity. Isoimperatorin (7), Osthol (8a) and suberosin (8b) were isolated from Arracacia tolucensis exihibiting antitubercular activity MIC at 64.0 lg-mL À1 , 32.0 lg-mL À1 and 16 lg-mL À1 respectively (Fig. 1). 10 Other coumarin derivatives such as ferulenol (9) have also been reported to exhibit potent antitubercular activity (MIC = 2.0 lg-mL À1) against other species of Mycobacterium. 11,12 Similarly, chalcones such as licochalcone A (10), present in Glycyrrhiza inflata exhibited potent antitubercular activity (MIC = 7.1 lg-mL À1). 13 Furthermore, pyranones such as 11 and 12 present in Piper sanctum have been reported to have potent antitubercular activity in Mycobacterium tuberculosis (MIC = 32 lg-mL À1 and 4.0 lg-mL À1 , respectively) (Fig. 1). 14 It is known that a moderate to high level of lipophilicity of the compounds often attributes better antitubercular activity. In the present study, taking structural learning from natural coumarins, chalcones and pyranones, we synthesized some lipophilic chalcones of prototype I and their conformationally re-stricted analogues (styrenylchromanone) based on prototype II which may be considered as hybrid of coumarin and chalcone nucleus. Further, for activity modulation, we planned to have a nitrogen moiety as it is essentially present in all the frontline anti-tubercular drugs (Fig. 2). The synthesized compounds were investigated for their antitu-bercular potential in Mycobacterium tuberculosis H 37 R V strain radiometrically. Further, 16, 24, 25a, 25c and 26, which showed significant antitubercular activity were evaluated for their toxicity
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    ABSTRACT: A new approach to synthesize a homologous series of 14-, 15-, and 16-membered drug-like, macrocyclic glycoconjugates involving TBAHS promoted azide-propenone intramolecular cycloaddition in designed C-glycopyranosyl butenones from a simple sugar d-glucose and d-mannose is reported.
    Organic Letters 08/2012; 14(17):4306-9. · 6.14 Impact Factor
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    ABSTRACT: Cytokines are known as important regulators of the entire gamut of cancer from initiation, invasion and metastasis. This fact and plethora of gene polymorphism data prompted us to investigate cytokine gene polymorphisms in breast cancer (BC) patients. Selected polymorphisms in the IL-1β [-511 T>C (rs16944) and +3954 C>T (rs1143634)]; IL-6 [-174 G>C (rs1800795)]; IL-10 [-1082 A>G (rs1800896), -819 T>C (rs1800871) and -592 A>C (rs1800872)] genes were genotyped in 200 BC patients and 200 healthy volunteers in a case-control study using PCR-RFLP and direct DNA sequencing techniques. Peripheral cytokine levels were measured using ELISA. Allele and genotype data were analyzed for significance of differences between cases and controls using Chi-Square [χ(2)] test. Two sided P-values of less than 0.05 were considered to be statistically significant. Peripheral level of all three cytokines did not show any significant difference between cases and controls. Allele and genotype frequency of IL-1β [-511 T>C (rs16944)] did not show any difference between cases and controls. On the other hand mutant allele and genotype at IL-1β [+3954 C>T (rs1143634)] associated with increased risk of BC. This was also true for pre-menopausal cases and for mutant genotype in post-menopausal cases. Mutant allele and genotypes at IL-6 [-174 G>C (rs1800795)] appeared to be protective in nature such that controls had a higher frequency of both mutant alleles and genotypes. None of the three SNPs in IL-10 gene associated with risk of BC, except significant association of mutant allele and genotypes of -1082 A>G (rs1800896) polymorphism with postmenopausal BC. Mutant allele and genotype at IL-1β [+3954 C>T (rs1143634)] site associated with increased BC risk, while mutant allele and genotypes at IL-6 [-174 G>C (rs1800795)] polymorphism appeared to be protective. Also, there was significant association of mutant allele and genotypes of IL-10 [-1082 A>G (rs1800896)] with postmenopausal BC. None of the other polymorphisms investigated appear to affect BC risk.
    Cytokine 07/2012; 60(1):122-8. · 2.52 Impact Factor
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    ABSTRACT: Wrightia tomentosa Roem. & Schult. (Apocynaceae) is known in the traditional medicine for anti-cancer activity along with other broad indications like snake and scorpion bites, renal complications, menstrual disorders etc. However, the anti-cancer activity of this plant or its constituents has never been studied systematically in any cancer types so far. To evaluate the anti-cancer activities of the ethanolic extract of W. tomentosa and identified constituent active molecule(s) against breast cancer. Powdered leaves of W. tomentosa were extracted with ethanol. The ethanolic extract, subsequent hexane fractions and fraction F-4 of W. tomentosa were tested for its anti-proliferative and pro-apoptotic effects in breast cancer cells MCF-7 and MDA-MB-231. The ethanolic extract, subsequent hexane fractions and fraction F-4 of W. tomentosa inhibited the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231. The fraction F-4 obtained from hexane fraction inhibited proliferation of MCF-7 and MDA-MB-231 cells in concentration and time dependent manner with IC₅₀ of 50 μg/ml and 30 μg/ml for 24 h, 28 μg/ml and 22 μg/ml for 48 h and 25 μg/ml and 20 μg/ml for 72 h respectively. The fraction F-4 induced G1 cell cycle arrest, reactive oxygen species (ROS) generation, loss of mitochondrial membrane potential and subsequent apoptosis. Apoptosis is indicated in terms of increased Bax/Bcl-2 ratio, enhanced Annexin-V positivity, caspase 8 activation and DNA fragmentation. The active molecule isolated from fraction F-4, oleanolic acid and urosolic acid inhibited cell proliferation of MCF-7 and MDA-MB-231 cells at IC₅₀ value of 7.5 μM and 7.0 μM respectively, whereas there is devoid of significant cell inhibiting activity in non-cancer originated cells, HEK-293. In both MCF-7 and MDA-MB-231, oleanolic acid and urosolic acid induced cell cycle arrest and apoptosis as indicated by significant increase in Annexin-V positive apoptotic cell counts. Our results suggest that W. tomentosa extracts has significant anti-cancer activity against breast cancer cells due to induction of apoptosis pathway. Olenolic and urosolic acid are important constituent molecules in the extract responsible for anti-cancer activity of W. tomentosa.
    Journal of ethnopharmacology 06/2012; 142(1):72-9. · 2.32 Impact Factor
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    ABSTRACT: Phenstatin analogues were synthesized on steroidal framework, for selective targeting of breast cancer cells. These analogues were evaluated for anticancer efficacy against breast cancer cell lines. Analogues 12 and 19 exhibited significant anticancer activity against MCF-7, hormone dependent breast cancer cell line. While analogues 10-14 exhibited significant anticancer activity against MDA-MB-231, hormone independent breast cancer cell line. Compound 10 showed significant oestrogen antagonistic activities with low agonistic activity in in vivo rat model. These analogues also retain tubulin polymerization inhibition activity. The most active analogue 10 was found to be non-toxic in Swiss albino mice up to 300 mg/kg dose. Gallic acid based phenstatin analogues may further be optimized as selective anti-breast cancer agents.
    Steroids 04/2012; 77(8-9):878-86. · 2.80 Impact Factor
  • Hamidullah, Bendangla Changkija, Rituraj Konwar
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    ABSTRACT: Cytokines are low molecular weight regulatory proteins or glycoprotein that modulates the intensity and duration of immune response by stimulating or inhibiting the activation, proliferation, and/or differentiation of target cells. Different cytokines are known to have diverse role in breast cancer initiation and progression. Interleukin-10 (IL-10), a pleiotropic anti-inflammatory cytokine, induces immunosuppression and assists in escape from tumor immune surveillance. Like several other cytokines, IL-10 also can exert dual proliferative and inhibitory effect on breast tumor cells indicating a complex role of IL-10 in breast cancer initiation and progression. In this review, we tried to put together a comprehensive current view on significance of IL-10 in promotion, inhibition, and importance as prognosticator in breast cancer based on in vitro, in vivo, and clinical evidences. For literature collection, we conducted PubMed search with keywords "IL-10" and "breast cancer".
    Breast Cancer Research and Treatment 11/2011; 133(1):11-21. · 4.47 Impact Factor

Publication Stats

249 Citations
111.30 Total Impact Points

Institutions

  • 2014
    • Academy of Scientific and Innovative Research
      New Dilli, NCT, India
  • 2011–2014
    • CSIR Central Road Research Institute
      New Dilli, NCT, India
    • American Association of Oral and Maxillofacial Surgeons
      India Hook, South Carolina, United States
  • 2007–2014
    • Central Drug Research Institute
      • • Medicinal and Process Chemistry Division (CDRI)
      • • Endocrinology Division (CDRI)
      Lakhnau, Uttar Pradesh, India
  • 2013
    • King George's Medical University
      Lakhnau, Uttar Pradesh, India
  • 2012
    • Central Institute of Medicinal and Aromatic Plants
      • Department of Metabolic and Structural Biology (CIMAP)
      Lakhnau, Uttar Pradesh, India
  • 2010
    • The Ohio State University
      Columbus, Ohio, United States
  • 2008–2009
    • University of Lucknow
      • Department of Zoology
      Lucknow, Uttar Pradesh, India