Identification and characterization of a new tubulin-binding tetrasubstituted brominated pyrrole

Molecular Pharmacology

Volumn 72, Issue 1, 2007, Pages 132-140

  Mooberry, Susan L ^a   Weiderhold, Kimberly N ^a   Dakshanamurthy, Sivanesan ^b   Hamel, Ernest ^c   Banner, Edith J ^d   Kharlamova, Anastasia ^d   Hempel, Jonathan ^d   Gupton, John T ^d   Brown, Milton L ^b  

^a SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

^d UNIVERSITY OF RICHMOND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIBROMO 4 (3,4 DIMETHOXYPHENYL) 1H PYRROLE 2 CARBOXYLIC ACID ETHYL ESTER; ALPHA TUBULIN; BETA TUBULIN; BROMINE; CASPASE 3; COLCHICINE DERIVATIVE; GLYCOPROTEIN P; JG 0314; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PROTEIN BCL 2; PYRROLE; TUBULIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; COMPARATIVE STUDY; CONTROLLED STUDY; DOSE RESPONSE; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG MECHANISM; EMBRYO; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; MICROTUBULE; MITOSIS SPINDLE; MOLECULAR MODEL; MOUSE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN PHOSPHORYLATION; PROTEIN TRANSPORT; RAT; TUMOR VOLUME; XENOGRAFT;

ANTINEOPLASTIC AGENTS; CELL CYCLE; COLCHICINE; DRUG RESISTANCE, NEOPLASM; MICROTUBULES; MODELS, MOLECULAR; P-GLYCOPROTEIN; PHOSPHORYLATION; POLY(ADP-RIBOSE) POLYMERASES; PROTO-ONCOGENE PROTEINS C-BCL-2; PYRROLES; TUBULIN;

EID: 34347236860     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.107.034876     Document Type: Article

References (39)

1. Bai R, Pei XF, Boye O, Getahun Z, Grover S, Bekisz J, Nguyen NY, Brossi A, and Hamel E (1996) Identification of cysteine 354 of β-tubulin as part of the binding site for the A ring of colchicine. J Biol Chem 271:12639-12645.
2. Banwell MG, Flynn BL, Hamel E, and Hockless DCR (1997) Convergent synthesis of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners. Chem Commun 2:207-208.
3. Bayly C, Cieplak P, Cornell WD, and Kollman PA (1993) A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J Phys Chem 97:10269-10280.
4. Blagosklonny MV, Darzynkiewicz Z, Halicka HD, Pozarowski P, Demidenko ZN, Barry JJ, Kamath KR, and Herrmann RA (2004) Paclitaxel induces primary and postmitotic G1 arrest in human arterial smooth muscle cells. Cell Cycle 3:1050-1056.
5. Borisy GG (1972) A rapid method for quantitative determination of microtubule protein using DEAE-cellulose filters. Anal Biochem 50:373-385.
6. Boyd MR and Paull KD (1995) Some practical considerations and applications of the National Cancer Institute in vitro anticancer discovery screen. Drug Dev Res 34:91-109.
7. Burnham BS, Gupton JT, Krumpe K, Webb T, Shuford J, Bowers B, Warren AE, Barnes C, and Hall IH (1998) Cytotoxicity of substituted alkyl-3,4-bis(4- methoxyphenyl)pyrrole-2-carboxylates in L1210 lymphoid leukemia cells. Arch Pharm (Weinheim) 331:337-341.
8. Case DA, Darden TA, Cheatham TE III, Simmerling CL, Wang J, Duke RE, Luo R, Merz KM, Wang B, Pearlman DA, et al. (2004) AMBER 8. University of California at San Francisco, San Francisco.
9. Charan RD, Schlingmann G, Bernan VS, Feng X, and Carter GT (2006). Dioxapyrrolomycin biosynthesis in Streptomyces fumanus. J Nat Prod 69:29-33.
10. Chaudhary PM and Roninson IB (1991) Expression and activity of P-glycoprotein, a multidrug efflux pump, in human hematopoietic stem cells. Cell 66:85-94.
11. Chen JG and Horwitz SB (2002) Differential mitotic responses to microtubule-stabilizing and -destabilizing drugs. Cancer Res 62:1935-1938.
12. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, et al. (2003) Gaussian 03. Gaussian, Inc., Pittsburgh, PA.
13. Griggs J, Metcalfe JC, and Hesketh R (2001) Targeting tumour vasculature: the development of combretastatin A4. Lancet Oncol 2:82-87.
14. Gupton JT (2006) Pyrrole natural products with antitumor properties, in Heterocyclic Antitumor Antibiotics: Topics in Heterocyclic Chemistry (Lee M ed) pp 53-92, Springer-Verlag, Berlin.
15. Gupton JT, Burham BS, Byrd BD, Krumpe KE, Stokes C, Shuford J, Winkle S, Webb T, Warren AE, Barnes CR, et al. (1999) The cytotoxicity and mode of action of 2,3,4-trisubstituted pyrroles and related derivatives in human Tmolt4 leukemia cells. Pharmazie 54:691-697.
16. Gupton JT, Burham BS, Krumpe K, Du K, Sikorski JA, Warren AE, Barnes CR, and Hall IH (2000) Synthesis and cytotoxicity of 2,4-disubstituted and 2,3,4-trisubstituted brominated pyrroles in murine and human cultured tumor cells. Arch Pharm (Weinheim) 333:3-9.
17. Haldar S, Basu A, and Croce CM (1997) Bcl2 is the guardian of microtubule integrity. Cancer Res 57:229-233.
18. Hamel E (2003) Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin. Cell Biochem Biophys 38:1-22.
19. Jordan MA and Wilson L (2004) Microtubules as a target for anticancer drugs. Nat Rev Cancer 4:253-265.
20. Kong Y, Grembecka J, Edler MC, Hamel E, Mooberry SL, Sabat M, Rieger J, and Brown ML (2005) Structure-based discovery of a boronic acid bioisostere of combretastatin A-4. Chem Biol 12:1007-1014.
21. Krishan A (1975) Rapid flow cytofluorimetric analysis of mammalian cell cycle by propidium iodide staining. J Cell Biol 66:188-193.
22. Lawrence NJ and McGown AT (2005) The chemistry and biology of antimitotic chalcones and related enone systems. Curr Pharm Des 11:1679-1693.
23. Lin CM, Ho HH, Pettit GR, and Hamel E (1989) Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 28:6984-6991.
24. Maple J, Hwang M-J, Stockfisch T, Dinur U, Waldman M, Ewig C, and Hagler A (2004) Derivation of class II force fields. I. Methodology and quantum force field for alkyl functional group and alkane molecules. J Comput Chem 15:162-182.
25. Minderman H, Vanhoefer U, Toth K, Yin MB, Minderman MD, Wrzosek C, Slovak ML, and Rustum YM (1996) DiOC2(3) is not a substrate for multidrug resistance protein (MRP)-mediated drug efflux. Cytometry 25:14-20.
26. Mooberry SL (2003) New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr Opin Oncol 15:425-430.
27. Morris G, Goodsell D, Halliday R, Huey R, Hart W, Belew R, and Olson A (1999) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662.
28. Nogales E, Wolf SG, and Downing KH (1998) Structure of the alpha beta tubulin dimer by electron crystallography. Nature 391:199-203.
29. Rarey M, Kramer B, Lengauer T, and Klebe G (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261:470-489.
30. Ravelli RB, Gigant B, Curmi PA, Jourdain I, Lachkar S, Sobel A, and Knossow M (2004) Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain. Nature 428:198-202.
31. Scudiero DA, Monks A, and Sausville EA (1998) Cell line designation change: multidrug-resistant cell line in the NCI anticancer screen. J Natl Cancer Inst 90:862.
32. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, and Boyd MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107-1112.
33. Tinley TL, Leal RM, Randall-Hlubek DA, Cessac JW, Wilkens LR, Rao PN, and Mooberry SL (2003a) Novel 2-methoxyestradiol analogues with antitumor activity. Cancer Res 63:1538-1549.
34. Tinley TL, Randall-Hlubek DA, Leal RM, Jackson EM, Cessac JW, Quada JC Jr, Hemscheidt TK, and Mooberry SL (2003b) Taccalonolides E and A: plant-derived steroids with microtubule-stabilizing activity. Cancer Res 63:3211-3220.
35. Uppuluri S, Knipling L, Sackett DL, and Wolff J (1993) Localization of the colchicine-binding site of tubulin. Proc Natl Acad Sci U S A 90:11598-11602.
36. Verdier-Pinard P, Lai JY, Yoo HD, Yu J, Marquez B, Nagle DG, Nambu M, White JD, Falck JR, Gerwick WH, et al. (1998) Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells. Mol Pharmacol 53:62-76.
37. Wang J, Wolf R, Caldwell J, Kollman P, and Case D (2004) Development and testing of a general amber force field. J Comput Chem 25:1157-1174.
38. Weiderhold KN, Randall-Hlubek DA, Polin LA, Hamel E, and Mooberry SL (2006) CB694, a novel antimitotic with antitumor activities. Int J Cancer 118:1032-1040.
39. Yoshida WY, Lee KK, Carroll AR, and Scheuer PJ (1992) A complex pyrrolooxazinone and its iodo derivative isolated from a tunicate. Helv Chim Acta 75:1271-1275.