Research Article
Year 2015,
Volume: 19 Issue: 3, 259 - 267, 29.06.2015
Abstract
References
- Hixson LJ, Alberts DS, Krutzsch M, Einsphar J, Brendel K. Gross PH, Paranka NS, Baier M, Emerson S, Pamukcu R, Burt RW. Antiproliferative effect of nonsteroidal antiinflammatory drugs against human colon cancer cells. Cancer Epidemiol Biomarkers Prev 1994;3: 433-8.
- Lu D, Cottam HB, Corr M, Carson DA. Repression of β-catenin function in malignant cells by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci 2005;102: 18567-71.
- Duffy CP, Elliott CJ, O’Connor RA, Heenan MM, Coyle S, Cleary IM, Kavanagh K, Verhaegen S, O’Loughlin CM, NicAmhlaoibh R, Clynes M. Enhancement of chemotherapeutic drug toxicity to human tumour cells in vitro by a subset of non-steroidal anti-inflammatory drugs (NSAIDs). Eur J Cancer 1998; 43:1250-9.
- Kalyoncuoğlu N, Rollas S, Sür-Altıner D, Yeğenoğlu Y, Anğ Ö. 1-[p-(Benzoylamino)benzoyl]-4-substituted thiosemicarbazides: Synthesis and antibacterial and antifungal activities. Pharmazie 1992;47: 796-7.
- Rollas S, Karakuş S, Durgun BB. Synthesis and Antimicrobial Activity of Some 1,4-Disubstituted Thiosemicarbazide and 2,5-Disubstituted 1,3,4-Thiadiazole Derivatives. Il Farmaco 1996;51: 811-4.
- Al-Saadi MS, Faidallah HM, Rostom S, A. F. Synthesis and Biological Evaluation of Some 2,4,5-Trisubstituted Thiazole Derivatives as Potential Antimicrobial and Anticancer Agents. Arch Pharm Chem Life Sci 2008;341: 424
- Sun Y, Wang W, Sun Y, Han M. Synthesis and biological evaluation of a novel stem/progenitor cells proliferation activator: 4-(4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenyl) thiosemicarbazie (Stemazole). Eur J Med Chem 2011;46: 2930
- He J, Wang X, Zhao X, Liang Y, He H, Fu L. Synthesis and antitumor activity of novel quinazolinone derivatives containing thiosemikarbazide moiety. Eur J Med Chem 2012;54: 925-30.
- Çıkla P, Arora P, Basu A, Talele TT, Kaushik-Basu N, Küçükgüzel ŞG. Etodolac Thiosemicarbazides: a novel class of hepatitis C virus NS5B polymerase inhibitors. Marmara Pharm j 2013;17: 138-46.
- Singhal S, Arora S, Agarwal S, Sharma R, Singhal N. A review on potential biological activities of thiosemicarbazides. World J Pharm and Pharm Sci 2013;2: 4661-81.
- Siwek A, Staczek P, Wujec M, Bielawski K, Bielawska A, Paneth P. Cytotoxic effect and molecular docking of 4-ethoxycarbonylmethyl-1-(piperidin-4-ylcarbonyl)- thiosemicarbazide-a novel topoisomerase II inhibitör. J Mol Mod 2013;19: 1319-24.
- Arora S, Agarwal S, Singhal S. Anticancer Activities Of Thiosemicarbazides/Thiosemicarbazones: A Review. Int J Pharm Pharm Sci 2014;6.
- Mavrova AT, Wessilinova D, Tsenov JA, Lubenov LA. Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur J Med Chem 2014;86: 676-83.
- Ünver Y, Sancak K, Çelik F, Birinci E, Küçük M, Soylu S, Arslan Burnaz N. New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazoleethiols. Eur J Med Chem 2014;84: 639-50.
- Koç D. Tolmetin Üzerinden Hidrazit-Hidrazonların Sentezi Ve Biyolojik Etkileri. M.Ü. Institute of Health Sciences, Master Degree Thesis, 2014, İstanbul (Advisor: Prof. Dr. Ş. Güniz Küçükgüzel).
- Küçükgüzel ŞG, Koç D, Çıkla-Süzgün P, Özsavcı D, Bingöl-Özakpınar Ö, Mega-Tiber P, Orun O, Erzincan P, Erdem SS, Şahin F. Synthesıs of Tolmetın Hydrazide- Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Arch Pharm (Weinheim) 2015; In Press.
- Rollas S. Bazı l-aroil-4-alkil/ariltiyosemikarbazidler I. Doğa Bilim Derg 1983;7: 65-73.
- Durgun BB, Rollas S, Apaydın S, Öztürk R. Synthesis and antimicrobial activity of some new 1-[4-(4-fluorobenzoylamino)-benzoyl]-4-substituted thiosemicarbazides. Drug Metab Drug Interact 1995;12: 145
- Doğan HN, Rollas S, Erdeniz H. Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy- 2-naphthoic acid hydrazide derivatives. Il Farmaco 1998;53: 462
- Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, Characterisation and Biological Activity of Novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002;37: 197-206.
- Küçükgüzel ŞG, Kocatepe A, Clercq ED, Şahin F, Güllüce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem 2006;41: 353-9.
- Tatar E, Küçükgüzel İ, De Clercq, Şahin F, Güllüce M. Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)- 4-(methylthio)butyryl]-4-alkyl/arylalkyl thiosemicarbazides. Arkivov 2008;14: 191-210.
- Ferlay J, Steliarova-Foucher E, Lortet-Tieulent J. Cancer incidence and mortality patterns in Europe: Estimates for 40 countries in 2012. Eur J Cancer 2013;49: 1374-1403.
- Demertzi DK, Domopoulou A, Demertzis MA. Palladium (II) Complexes of 2-Acetylpyridine N(4)- Methyl, N(4)-Ethyl and N(4)-Phenyl - Thiosemicarbazones. Crystal Structure of Chloro (2-Acetylpyridine N(4)- Methylthiosemicarbazonato) Palladium (II). Synthesis, Spectral Studies, In vitro and In vivo Antitumour Activity. J Inorg Biochem 1997;68: 147-55.
- Greenlee RT, Murray T, Bolden S, Wingo PA. Cancer statistics. CA Cancer J Clin 2000;50: 7-33.
- Alvero AB, Chen W, Sartorelli AC, et al. Triapine (3-amino-2-carboxaldehyde thiosemicarbazone) Induces Apoptosis in Ovarian Cancer Cells. J Soc Gynecol Investig 2006;13: 145-52.
- Yu Y, Wong J, Lovejoy DB. Chelators at the cancer coalface: desferrioxamine to Triapine and beyond. Clin Cancer Res 2006;12: 6876-83.
- Ferrari BM, Capacchi S, Pelosi G. Synthesis, Structural Characterization and Biological Activity of Helicin Thiosemicarbazone Monohydrate and a Copper (II) Complex of Salicylaldehyde Thiosemicarbazone. Inorg Chimica Acta 1999;286: 134-41.
- Beytur A, Tekin S, Keleştimur T, Ergin Z, Sandal S. Yeni Sentezlenen Bir Tiyosemikarbazon Türevinin Prostat Kanseri Hücre Kültürleri Üzerine Antikanserojenik Özelliklerinin Belirlenmesi: In vitro Bir Çalışma. FÜ Sağ Bil Tıp Derg 2011;25: 25-32.
- Lu P, Weaver VM, Werb Z. The extracellular matrix: A dynamic niche in cancer progression J Biol 2012;196: 395- 40
- Gross J, Lapiere CM. Collagenolytıc Actıvıty In Amphıbıan Tıssues: A Tıssue Culture Assay. Proc Natl Acad Sci USA 1962;48: 1014-22.
- Itoh Y, Nagase H. Matrix metalloproteinases in cancer. Essays Biochem 2002;38: 21-36.
- Zhang L, Shi J, Feng J, Klocker H, Lee C, Zhang J. Type IV collagenase (matrix metalloproteinase-2 and -9) in prostate cancer. Prostate Cancer Prostatic Dis 2004;7: 327-32.
- Öncel M. Matriks Metalloproteinazlar ve Kanser. Eur J Basic Med Sci 2012;2: 91-100.
Year 2015,
Volume: 19 Issue: 3, 259 - 267, 29.06.2015
Abstract
A novel series of new tolmetin hydrazide derivatives, N-Alkyl/Arylsubstitued- 2-{[1-methyl-5-(4-methylbenzoyl)-1H-pyrol-2-yl]acetyl}hydrazinecarbothioamides [4a-j] have been synthesized in this study. The structures of the new compounds were determined by spectral (FT-IR, 1H-NMR, 13C-NMR and 2D-NMR) methods and their purity were proven by elemental analysis and TLC. Tolmetin [1] and N-(4-fluorophenyl) -2-{[1-methyl-5-(4-methylbenzoyl)-1H-pyrol-2-yl]acetyl}hydrazinecarbothioamide [SGK-524; 4d] were evaluated for in vitro using the MTT colorimetric method for anticancer activity. Androjen-independed human prostate cancer cell line PC-3 (ATCC, CRL-1435) , human colon cancer cell lines HCT-116 (ATCC, CCL-247) and HT-29 (ATCC, HTB-38) were used in this study. Compound 4d exhibited anticancer activity against PC-3 whereas Tolmetin showed minor activity comparing to compound 4d.
Keywords
References
- Hixson LJ, Alberts DS, Krutzsch M, Einsphar J, Brendel K. Gross PH, Paranka NS, Baier M, Emerson S, Pamukcu R, Burt RW. Antiproliferative effect of nonsteroidal antiinflammatory drugs against human colon cancer cells. Cancer Epidemiol Biomarkers Prev 1994;3: 433-8.
- Lu D, Cottam HB, Corr M, Carson DA. Repression of β-catenin function in malignant cells by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci 2005;102: 18567-71.
- Duffy CP, Elliott CJ, O’Connor RA, Heenan MM, Coyle S, Cleary IM, Kavanagh K, Verhaegen S, O’Loughlin CM, NicAmhlaoibh R, Clynes M. Enhancement of chemotherapeutic drug toxicity to human tumour cells in vitro by a subset of non-steroidal anti-inflammatory drugs (NSAIDs). Eur J Cancer 1998; 43:1250-9.
- Kalyoncuoğlu N, Rollas S, Sür-Altıner D, Yeğenoğlu Y, Anğ Ö. 1-[p-(Benzoylamino)benzoyl]-4-substituted thiosemicarbazides: Synthesis and antibacterial and antifungal activities. Pharmazie 1992;47: 796-7.
- Rollas S, Karakuş S, Durgun BB. Synthesis and Antimicrobial Activity of Some 1,4-Disubstituted Thiosemicarbazide and 2,5-Disubstituted 1,3,4-Thiadiazole Derivatives. Il Farmaco 1996;51: 811-4.
- Al-Saadi MS, Faidallah HM, Rostom S, A. F. Synthesis and Biological Evaluation of Some 2,4,5-Trisubstituted Thiazole Derivatives as Potential Antimicrobial and Anticancer Agents. Arch Pharm Chem Life Sci 2008;341: 424
- Sun Y, Wang W, Sun Y, Han M. Synthesis and biological evaluation of a novel stem/progenitor cells proliferation activator: 4-(4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenyl) thiosemicarbazie (Stemazole). Eur J Med Chem 2011;46: 2930
- He J, Wang X, Zhao X, Liang Y, He H, Fu L. Synthesis and antitumor activity of novel quinazolinone derivatives containing thiosemikarbazide moiety. Eur J Med Chem 2012;54: 925-30.
- Çıkla P, Arora P, Basu A, Talele TT, Kaushik-Basu N, Küçükgüzel ŞG. Etodolac Thiosemicarbazides: a novel class of hepatitis C virus NS5B polymerase inhibitors. Marmara Pharm j 2013;17: 138-46.
- Singhal S, Arora S, Agarwal S, Sharma R, Singhal N. A review on potential biological activities of thiosemicarbazides. World J Pharm and Pharm Sci 2013;2: 4661-81.
- Siwek A, Staczek P, Wujec M, Bielawski K, Bielawska A, Paneth P. Cytotoxic effect and molecular docking of 4-ethoxycarbonylmethyl-1-(piperidin-4-ylcarbonyl)- thiosemicarbazide-a novel topoisomerase II inhibitör. J Mol Mod 2013;19: 1319-24.
- Arora S, Agarwal S, Singhal S. Anticancer Activities Of Thiosemicarbazides/Thiosemicarbazones: A Review. Int J Pharm Pharm Sci 2014;6.
- Mavrova AT, Wessilinova D, Tsenov JA, Lubenov LA. Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety. Eur J Med Chem 2014;86: 676-83.
- Ünver Y, Sancak K, Çelik F, Birinci E, Küçük M, Soylu S, Arslan Burnaz N. New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazoleethiols. Eur J Med Chem 2014;84: 639-50.
- Koç D. Tolmetin Üzerinden Hidrazit-Hidrazonların Sentezi Ve Biyolojik Etkileri. M.Ü. Institute of Health Sciences, Master Degree Thesis, 2014, İstanbul (Advisor: Prof. Dr. Ş. Güniz Küçükgüzel).
- Küçükgüzel ŞG, Koç D, Çıkla-Süzgün P, Özsavcı D, Bingöl-Özakpınar Ö, Mega-Tiber P, Orun O, Erzincan P, Erdem SS, Şahin F. Synthesıs of Tolmetın Hydrazide- Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Arch Pharm (Weinheim) 2015; In Press.
- Rollas S. Bazı l-aroil-4-alkil/ariltiyosemikarbazidler I. Doğa Bilim Derg 1983;7: 65-73.
- Durgun BB, Rollas S, Apaydın S, Öztürk R. Synthesis and antimicrobial activity of some new 1-[4-(4-fluorobenzoylamino)-benzoyl]-4-substituted thiosemicarbazides. Drug Metab Drug Interact 1995;12: 145
- Doğan HN, Rollas S, Erdeniz H. Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy- 2-naphthoic acid hydrazide derivatives. Il Farmaco 1998;53: 462
- Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, Characterisation and Biological Activity of Novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002;37: 197-206.
- Küçükgüzel ŞG, Kocatepe A, Clercq ED, Şahin F, Güllüce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem 2006;41: 353-9.
- Tatar E, Küçükgüzel İ, De Clercq, Şahin F, Güllüce M. Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)- 4-(methylthio)butyryl]-4-alkyl/arylalkyl thiosemicarbazides. Arkivov 2008;14: 191-210.
- Ferlay J, Steliarova-Foucher E, Lortet-Tieulent J. Cancer incidence and mortality patterns in Europe: Estimates for 40 countries in 2012. Eur J Cancer 2013;49: 1374-1403.
- Demertzi DK, Domopoulou A, Demertzis MA. Palladium (II) Complexes of 2-Acetylpyridine N(4)- Methyl, N(4)-Ethyl and N(4)-Phenyl - Thiosemicarbazones. Crystal Structure of Chloro (2-Acetylpyridine N(4)- Methylthiosemicarbazonato) Palladium (II). Synthesis, Spectral Studies, In vitro and In vivo Antitumour Activity. J Inorg Biochem 1997;68: 147-55.
- Greenlee RT, Murray T, Bolden S, Wingo PA. Cancer statistics. CA Cancer J Clin 2000;50: 7-33.
- Alvero AB, Chen W, Sartorelli AC, et al. Triapine (3-amino-2-carboxaldehyde thiosemicarbazone) Induces Apoptosis in Ovarian Cancer Cells. J Soc Gynecol Investig 2006;13: 145-52.
- Yu Y, Wong J, Lovejoy DB. Chelators at the cancer coalface: desferrioxamine to Triapine and beyond. Clin Cancer Res 2006;12: 6876-83.
- Ferrari BM, Capacchi S, Pelosi G. Synthesis, Structural Characterization and Biological Activity of Helicin Thiosemicarbazone Monohydrate and a Copper (II) Complex of Salicylaldehyde Thiosemicarbazone. Inorg Chimica Acta 1999;286: 134-41.
- Beytur A, Tekin S, Keleştimur T, Ergin Z, Sandal S. Yeni Sentezlenen Bir Tiyosemikarbazon Türevinin Prostat Kanseri Hücre Kültürleri Üzerine Antikanserojenik Özelliklerinin Belirlenmesi: In vitro Bir Çalışma. FÜ Sağ Bil Tıp Derg 2011;25: 25-32.
- Lu P, Weaver VM, Werb Z. The extracellular matrix: A dynamic niche in cancer progression J Biol 2012;196: 395- 40
- Gross J, Lapiere CM. Collagenolytıc Actıvıty In Amphıbıan Tıssues: A Tıssue Culture Assay. Proc Natl Acad Sci USA 1962;48: 1014-22.
- Itoh Y, Nagase H. Matrix metalloproteinases in cancer. Essays Biochem 2002;38: 21-36.
- Zhang L, Shi J, Feng J, Klocker H, Lee C, Zhang J. Type IV collagenase (matrix metalloproteinase-2 and -9) in prostate cancer. Prostate Cancer Prostatic Dis 2004;7: 327-32.
- Öncel M. Matriks Metalloproteinazlar ve Kanser. Eur J Basic Med Sci 2012;2: 91-100.
There are 34 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Health Care Administration |
| Journal Section | Articles |
| Authors | |
| Publication Date | June 29, 2015 |
| Published in Issue | Year 2015 Volume: 19 Issue: 3 |