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Volumn 31, Issue 3, 2011, Pages 831-842

In silico/in vitro study of hybrid D-modified steroidal alkylator anticancer activity using uridine phosphorylase as target protein

Author keywords

Hybrid steroidal alkylators; In silico molecular docking; In vitro assay; Mitrogen mustards; Pancreatic cancer cells; Uridine phosphorylase

Indexed keywords

3BETA HYDROXY 13ALPHA AMINO 13,17 SECO 5ALPHA ANDROSTAN 17 OIC 13,17 LACTAM [P [N,N BIS(2 CHLOROETHYL)AMINO]PHENYL]ACETATE; 3BETA HYDROXY 17 OXO 17ALPHA OXA 5ALPHA ANDROSTAN [P [N,N BIS (2 CHLOROETHYL)AMINO]PHENYL]ACETATE; 3BETA HYDROXY 5ALPHA ANDROSTAN [P [N,N BIS (2 CHLOROETHYL)AMINO]PHENYL]ACETATE; ALKYLATING AGENT; CYTOSTATIC AGENT; CYTOTOXIC AGENT; STEROID; UNCLASSIFIED DRUG; URIDINE PHOSPHORYLASE;

EID: 79956142333     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (6)

References (41)
  • 1
    • 0037677425 scopus 로고    scopus 로고
    • An overview on the antileukemic potential of D-homo-aza- and respective 17beta-acetamido-steroidal alkylating esters
    • DOI 10.1023/A:1022964225715
    • Camoutsis C and Trafalis DT: An overview on the antileukemic potential of D-homo-aza- and respective 17 beta-acetamido- steroidal alkylating esters. Invest New Drugs 21(1): 47-54, 2003. (Pubitemid 36628484)
    • (2003) Investigational New Drugs , vol.21 , Issue.1 , pp. 47-54
    • Camoutsis, C.1    Trafalis, D.T.P.2
  • 3
    • 33749354945 scopus 로고    scopus 로고
    • Hybrid aza-steroid alkylators in the treatment of colon cancer
    • Trafalis DT: Hybrid aza-steroid alkylators in the treatment of colon cancer. Cancer Lett 243(2): 202-210, 2006.
    • (2006) Cancer Lett , vol.243 , Issue.2 , pp. 202-210
    • Trafalis, D.T.1
  • 8
    • 23744448112 scopus 로고    scopus 로고
    • Research on the anti-tumour effect of steroid lactam alkylator (NSC-294859) in comparison with conventional chemotherapeutics in malignant melanoma
    • DOI 10.1097/00008390-200508000-00007
    • Trafalis DT, Camoutsis C and Papageorgiou A: Research on the anti-tumour effect of steroid lactam alkylator (NSC-294859) in comparison with conventional chemotherapeutics in malignant melanoma. Melanoma Res 15(4): 273-281, 2005. (Pubitemid 41127463)
    • (2005) Melanoma Research , vol.15 , Issue.4 , pp. 273-281
    • Trafalis, D.T.P.1    Camoutsis, C.2    Papageorgiou, A.3
  • 9
    • 33747206277 scopus 로고    scopus 로고
    • The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand-binding domain of estrogen receptor-alpha
    • Kontos M, Nikolopoulou M, Trafalis DT, Geromichalos GD, Koukoulitsa C, Camoutsis JC, Bastounis E and Karamanakos P: The effect of an estrone D-lactam steroid ester derivative on breast cancer cells and its predicted binding interactions with the ligand-binding domain of estrogen receptor-alpha. Oncol Res 16(3): 129-142, 2005.
    • (2005) Oncol Res , vol.16 , Issue.3 , pp. 129-142
    • Kontos, M.1    Nikolopoulou, M.2    Trafalis, D.T.3    Geromichalos, G.D.4    Koukoulitsa, C.5    Camoutsis, J.C.6    Bastounis, E.7    Karamanakos, P.8
  • 10
    • 2442659162 scopus 로고    scopus 로고
    • Preclinical evaluation of the homo-aza-steroid ester 13beta-hydroxy- 13alpha-amino-13,17-seco-5alpha-androstan-17-oic-13, 17-lactam-p-bis(2- chloroethyl)aminophenoxy acetate for the treatment of malignant melanoma
    • Trafalis DT, Camoutsis C, Karamanakos P, Arvanitis A, Tegou E, Ziras N and Athanassiou AE: Preclinical evaluation of the homo-aza-steroid ester 13beta-hydroxy-13alpha-amino-13,17- seco-5alpha-androstan-17-oic-13,17-lactam-p- bis(2-chloroethyl) aminophenoxy acetate for the treatment of malignant melanoma. J BUON 8(4): 333-339, 2003. (Pubitemid 38660085)
    • (2003) Journal of B.U.ON. , vol.8 , Issue.4 , pp. 333-339
    • Trafalis, D.T.P.1    Camoutsis, C..2    Karamanakos, P.3    Arvanitis, A.4    Tegou, E.5    Ziras, N.6    Athanassiou, A.E.7
  • 12
    • 0032707978 scopus 로고    scopus 로고
    • On the formation of steroidal amidoesters of 4-[N-N-bis(2-chloroethyl) amino]benzoic acid and their cytotoxic activity
    • Camoutsis C, Sambani C, Trafalis DT and Peristeris P: On the formation of steroidal amidoesters of 4-[N-N-bis(2-chloroethyl) amino]benzoic acid and their cytotoxic activity. Eur J Med Chem 34(7-8): 645-649, 1999.
    • (1999) Eur J Med Chem , vol.34 , Issue.7-8 , pp. 645-649
    • Camoutsis, C.1    Sambani, C.2    Trafalis, D.T.3    Peristeris, P.4
  • 13
    • 0037089505 scopus 로고    scopus 로고
    • Uridine phosphorylase (-/-) murine embryonic stem cells clarify the key role of this enzyme in the regulation of the pyrimidine salvage pathway and in the activation of fluoropyrimidines
    • Cao D, Russell RL, Zhang D, Leffert JJ and Pizzorno G: Uridine Phosphorylase (-/-) murine embryonic stem cells clarify the key role of this enzyme in the regulation of the pyrimidine salvage pathway and in the activation of fluoropyrimidines. Cancer Res 62: 2313-2317, 2002. (Pubitemid 34411710)
    • (2002) Cancer Research , vol.62 , Issue.8 , pp. 2313-2317
    • Cao, D.1    Russell, R.L.2    Zhang, D.3    Leffert, J.J.4    Pizzorno, G.5
  • 14
    • 33845955295 scopus 로고    scopus 로고
    • Up-regulated expression of the uridine phosphorylase gene in human gastric tumors is correlated with a favorable prognosis
    • Kawamura K, Takiguchi N, Wada A, Takenobu H, Kimura H, Soda H, Nagata M, Asano T and Tagawa M: Up-regulated expression of the uridine Phosphorylase gene in human gastric tumors is correlated with a favorable prognosis. Anticancer Res 26(6C): 4647-4651, 2006. (Pubitemid 46032094)
    • (2006) Anticancer Research , vol.26 , Issue.6 C , pp. 4647-4651
    • Kawamura, K.1    Takiguchi, N.2    Wada, A.3    Takenobu, H.4    Kimura, H.5    Soda, H.6    Nagata, M.7    Asano, T.8    Tagawa, M.9
  • 15
    • 33846426821 scopus 로고    scopus 로고
    • Upregulation of enzymes metabolizing 5-fluorouracil in colorectal cancer
    • DOI 10.1159/000098249
    • Matsusaka S, Yamasaki H, Fukushima M and Wakabayashi I: Upregulation of enzymes metabolizing 5-fluorouracil in colorectal cancer. Chemotherapy 53(1): 36-41, 2007. (Pubitemid 46143852)
    • (2007) Chemotherapy , vol.53 , Issue.1 , pp. 36-41
    • Matsusaka, S.1    Yamasaki, H.2    Fukushima, M.3    Wakabayashi, I.4
  • 16
    • 33744490347 scopus 로고    scopus 로고
    • Uridine Phosphorylase in breast cancer: A new prognostic factor?
    • Yan R, Wan L, Pizzorno G and Cao D: Uridine Phosphorylase in breast cancer: a new prognostic factor? Front Biosci 11: 2759-2766, 2006.
    • (2006) Front Biosci , vol.11 , pp. 2759-2766
    • Yan, R.1    Wan, L.2    Pizzorno, G.3    Cao, D.4
  • 17
    • 63849164243 scopus 로고    scopus 로고
    • Implications of the structure of human uridine Phosphorylase 1 on the development of novel inhibitors for improving the therapeutic window of fluoropyrimidine chemotherapy
    • Roosild TP, Castronovo S, Fabbiani M and Pizzorno G: Implications of the structure of human uridine Phosphorylase 1 on the development of novel inhibitors for improving the therapeutic window of fluoropyrimidine chemotherapy. BMC Struct Biol 9: 14, 2009.
    • (2009) BMC Struct Biol , vol.9 , pp. 14
    • Roosild, T.P.1    Castronovo, S.2    Fabbiani, M.3    Pizzorno, G.4
  • 18
    • 4644372634 scopus 로고    scopus 로고
    • Uridine phosphorylase: An important enzyme in pyrimidine metabolism and fluoropyrimidine activation
    • DOI 10.1358/dot.2004.40.5.850491
    • Cao D and Pizzorno G: Uridine phosophorylase: an important enzyme in pyrimidine metabolism and fluoropyrimidine activation. Drugs Today 40(5): 431-443, 2004. (Pubitemid 38858910)
    • (2004) Drugs of Today , vol.40 , Issue.5 , pp. 431-443
    • Cao, D.1    Pizzorno, G.2
  • 19
    • 0025278029 scopus 로고
    • Differential effects of 2,2'-anhydro-5-ethyluridine, a uridine phosphorylase inhibitor, on the antitumor activity of 5-fluorouridine and 5-fluoro-2'-deoxyuridine
    • DOI 10.1016/0006-2952(90)90270-U
    • Ligo M, Nishikata K, Nakajima Y, Szinai I, Veres Z, Szabolcs A and Clercq E: Differential effects of 2,2′-anhydro-5-ethyluridine, a uridine Phosphorylase inhibitor, on the antitumor activity of 5- fluorouridine and 5-fluoro-2′-deoxyuridine. Biochem Pharmacol 39: 1247-1253, 1990. (Pubitemid 20109242)
    • (1990) Biochemical Pharmacology , vol.39 , Issue.7 , pp. 1247-1253
    • Iigo, M.1    Nishikata, K.-I.2    Nakajima, Y.3    Szinai, I.4    Veres, Z.5    Szabolcs, A.6    De Clercq, E.7
  • 23
    • 67650924582 scopus 로고    scopus 로고
    • Pancreatic cancer: Molecular pathogenesis and new therapeutic targets
    • Wong HH and Lemoine NR: Pancreatic cancer: molecular pathogenesis and new therapeutic targets. Nat Rev Gastroenterol Hepatol 6(7): 412-422, 2009.
    • (2009) Nat Rev Gastroenterol Hepatol , vol.6 , Issue.7 , pp. 412-422
    • Wong, H.H.1    Lemoine, N.R.2
  • 24
    • 14244255577 scopus 로고    scopus 로고
    • RPL38, FOSL1, and UPP1 are predominantly expressed in the pancreatic ductal epithelium
    • Sahin F, Qiu W, Wilentz RE, Iacobuzio-Donahue CA, Grosmark A and Su GH: RPL38, FOSL1, and UPP1 are predominantly expressed in the pancreatic ductal epithelium. Pancreas 30(2): 158-167, 2005.
    • (2005) Pancreas , vol.30 , Issue.2 , pp. 158-167
    • Sahin, F.1    Qiu, W.2    Wilentz, R.E.3    Iacobuzio-Donahue, C.A.4    Grosmark, A.5    Su, G.H.6
  • 25
    • 0020058519 scopus 로고
    • Activity of 3β-hydroxy-13α-amino-13,17-seco-5α- androstane-17-oic-13,17-lactam(p-(bis( 2-chloroethyl)amino)-phenyl)acetate (NSC 290205) in murine solid tumors
    • Catsoulacos P and Wampler GL: Activity of 3β-hydroxy-13α- amino-13,17-seco-5α-androstane-17-oic-13,17-lactam(p-(bis(2- chloroethyl)amino) phenyl)acetate (NSC 290205) in murine solid tumors. Oncology 39: 109-112, 1982. (Pubitemid 12170238)
    • (1982) Oncology , vol.39 , Issue.2 , pp. 109-112
    • Catsoulacos, P.1    Wampler, G.L.2
  • 26
    • 0026322092 scopus 로고
    • Hybrid anticancer compounds. Steroidal lactam esters of carboxylic derivatives of N,N-bis (2-chloroethyl) aniline
    • Catsoulacos P and Catsoulacos D: Hybrid anticancer compounds. Steroidal lactam esters of carboxylic derivatives of N,N-bis (2-chloroethyl) aniline. Anticancer Res 11(5): 1773-1777, 1991.
    • (1991) Anticancer Res , vol.11 , Issue.5 , pp. 1773-1777
    • Catsoulacos, P.1    Catsoulacos, D.2
  • 27
    • 0342652475 scopus 로고
    • Aza-steroids. Beckmann rearrangement of 3β-acetoxy-5α- androstan-17-one oxime acetate with boron fluoride. Alkylting agents
    • Catsoulacos P and Boutis L: Aza-steroids. Beckmann rearrangement of 3β-acetoxy-5α-androstan-17-one oxime acetate with boron fluoride. Alkylting agents. Chim Ther 8: 215-217, 1973.
    • (1973) Chim Ther , vol.8 , pp. 215-217
    • Catsoulacos, P.1    Boutis, L.2
  • 28
    • 0022468204 scopus 로고
    • Comparison of in vitro activity of cytotoxic drugs towards human carcinoma and leukaemia cell lines
    • Finlay GJ, Wilson WR and Baguley BC: Comparison of in vitro activity of cytotoxic drugs towards human carcinoma and leukaemia cell lines. Eur J Cancer Clin Oncol 22: 655-662, 1986.
    • (1986) Eur J Cancer Clin Oncol , vol.22 , pp. 655-662
    • Finlay, G.J.1    Wilson, W.R.2    Baguley, B.C.3
  • 30
    • 0028906786 scopus 로고
    • Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen
    • Boyd MR and Pauli KD: Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Devel Res 34: 91-109, 1995.
    • (1995) Drug Devel Res , vol.34 , pp. 91-109
    • Boyd, M.R.1    Pauli, K.D.2
  • 31
    • 0024375273 scopus 로고
    • Use of oral uridine as a substitute for parenteral uridine rescue of 5-fluorouracil therapy, with and without the uridine phosphorylase inhibitor 5-benzylacyclouridine
    • Martin DS, Stolti RL and Sawyer RC: Use of oral uridine as substitute for parenteral uridine rescue of 5-fluorouracil therapy, with and without the uridine Phosphorylase inhibitor 5- benzylacyclouridine. Cancer Chemother Pharmacol 24: 9-14, 1989. (Pubitemid 19139983)
    • (1989) Cancer Chemotherapy and Pharmacology , vol.24 , Issue.1 , pp. 9-14
    • Martin, D.S.1    Stolfi, R.L.2    Sawyer, R.C.3
  • 32
    • 0034895775 scopus 로고    scopus 로고
    • Modulation of the pharmacokinetics of endofenous plasma uridine by 5-(phenylrhio)acyclouridine, a uridine Phosphorylase inhibitor: Implications for chemotherapy
    • al Safarjalani ON, Zhou XJ, Naguib FNM, Goudgaon NM, Schinazi RF and el Kouni MH: Modulation of the pharmacokinetics of endofenous plasma uridine by 5-(phenylrhio)acyclouridine, a uridine Phosphorylase inhibitor: implications for chemotherapy. Cancer Chemother Pharmacol 48: 145-150, 2001.
    • (2001) Cancer Chemother Pharmacol , vol.48 , pp. 145-150
    • Al Safarjalani, O.N.1    Zhou, X.J.2    Naguib, F.N.M.3    Goudgaon, N.M.4    Schinazi, R.F.5    El Kouni, M.H.6
  • 34
    • 0345059376 scopus 로고    scopus 로고
    • Announcing the worldwide Protein Data Bank
    • DOI 10.1038/nsb1203-980
    • Berman HM, Henrick K and Nakamura H: Announcing the worldwide Protein Data Bank. Nature Struct Biol 10(12): 980, 2003. (Pubitemid 37500485)
    • (2003) Nature Structural Biology , vol.10 , Issue.12 , pp. 980
    • Berman, H.1    Henrick, K.2    Nakamura, H.3
  • 35
    • 0017411710 scopus 로고
    • The protein data bank: A computer based archival file for macromolecular structures
    • Bernstein FC, Koetzle TF, Williams GJ, Meyer EE Jr, Brice MD, Rodgers JR, Kennard O, Shimanouchi T and Tasumi M: The Protein Data Bank: a computer-based archival file for macromolecular structures. J Mol Biol 112(3): 535-542, 1977. (Pubitemid 8109216)
    • (1977) Journal of Molecular Biology , vol.112 , Issue.3 , pp. 535-542
    • Bernstein, F.C.1    Koetzle, T.F.2    Williams, G.J.B.3
  • 36
    • 14444268539 scopus 로고    scopus 로고
    • Novel synthetic inhibitors of selectin-mediated cell adhesion: Synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-α-D-mannopyranosyloxy)phenyl] hexane (TBC1269)
    • DOI 10.1021/jm9704917
    • Kogan TP, Dupre B, Bui H, McAbee K, Kassir JM, Scott IL, Hu X, Vanderslice P, Beck PJ and Dixon RAF: Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6- bis[3-(3-carboxymethylphenyl) -4-(2-α-D-mannopyranosyloxy) phenyl]hexane (TBC1269). J Med Chem 41: 1099-1111, 1998. (Pubitemid 28207386)
    • (1998) Journal of Medicinal Chemistry , vol.41 , Issue.7 , pp. 1099-1111
    • Kogan, T.P.1    Dupre, B.2    Bui, H.3    McAbee, K.L.4    Kassir, J.M.5    Scott, I.L.6    Hu, X.7    Vanderslice, P.8    Beck, P.J.9    Dixon, R.A.F.10
  • 38
    • 32144463024 scopus 로고    scopus 로고
    • NSC 290205-based therapy in murine pancreatic adenocarcinoma PAN02 in combination with adriamycin ADR
    • Papageorgiou A, Andreadis Ch, Boutis A, Lialiaris Th and Mouratidou D: NSC 290205-based therapy in murine pancreatic adenocarcinoma PAN02 in combination with adriamycin ADR. Anticancer Res 26: 243-248, 2006.
    • (2006) Anticancer Res , vol.26 , pp. 243-248
    • Papageorgiou, A.1    Andreadis, C.2    Boutis, A.3    Lialiaris, Th.4    Mouratidou, D.5
  • 39
    • 0021277049 scopus 로고
    • Further studies on the anti-neoplastic activity of 3 β-hydroxy- 13α-amino-13,17-seco-5α-androstan-17-oic-13,17-lactam {p-[bis(2-chloroethyl)amino]-phenyl}acetate (NSC 290205)
    • Catsoulacos P: Further studies on the anti-neoplastic activity of 3 β-hydroxy-13α-amino-13,17-seco-5α-androstan-17-oic-13, 17-lactam {p-[bis(2-chloroethyl)amino]-phenyl}acetate (NSC 290205). Cancer Lett 22(2): 199-202, 1984.
    • (1984) Cancer Lett , vol.22 , Issue.2 , pp. 199-202
    • Catsoulacos, P.1
  • 40
    • 0017755947 scopus 로고
    • Antileukemic effect of homo aza steroidal ester of [p [bis(2 chloroethyl)amino]phenyl]acetic acid
    • Wampler G and Catsoulacos P: Antileukemic effect of homo aza-steroidal ester of [p-[bis(2-chloroethyl)amino]phenyl]acetic acid. Cancer Treat Rep 61(1): 37-41, 1977. (Pubitemid 8100653)
    • (1977) Cancer Treatment Reports , vol.61 , Issue.1 , pp. 37-41
    • Wampler, G.L.1    Catsoulacos, P.2
  • 41
    • 0023094388 scopus 로고
    • Induction of cytogenetic damage by modified steroidal derivatives of p-bis(2-chloroethyl)aminophenylacetic acid in human lymphocytes
    • Mourelatos D, Petrou C, Boutis L, Papageorgiou A, Catsoulacos P and Dozi-Vassiliades J: Induction of cytogenetic damage by modified steroidal derivatives of p-bis(2-chloroethyl) aminophenylacetic acid in human lymphocytes. Mutat Res 190(3): 205-210, 1987. (Pubitemid 17020129)
    • (1987) Mutation Research , vol.190 , Issue.3 , pp. 205-210
    • Mourelatos, D.1    Petrou, C.2    Boutis, L.3


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