Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors

European Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2011, Pages 2699-2708

  Reyes Ramírez, Adelfo ^a   Leyte Lugo, Martha ^b   Figueroa, Mario ^b   Serrano Alba, Trinidad ^a   González Andrade, Martín ^b   Mata, Rachel ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

1,2 Diphenylethanes; 1,3 Diphenylpropanes; 1,3 Diphenylpropenones; Calmodulin; Gigantol

Indexed keywords

1 (3 HYDROXY 5 METHOXYPHENYL) 3 (4 HYDROXY 3 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (4 HYDROXYPHENYL) 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1,3 DIMETHOXY 5 [2 (4 METHOXYPHENYL)ETHYL]BENZENE; 2 (3,5 DIMETHOXYBENZYL) 6 METHOXYPHENOL; 3 (1,3 BENZODIOXOL 5 YL) 1 (3 HYDROXYPHENYL)PROP 2 EN 1 ONE; 3 (3 HYDROXY 4 METHOXYPHENYL) 1 (3 HYDROXY 5 METHOXYPHENYL)PROP 2 EN 1 ONE; 3 [2 (1,3 BENZODIOXOL 5 YL)ETHYL] 5 METHOXYPHENOL; 3 [2 (1,3 BENZODIOXOL 5 YL)ETHYL]PHENOL; 3 [2 (4 ETHOXY 3 METHOXYPHENYL)ETHYL] 5 METHOXYPHENOL; 3 [2 (4 ETHOXY 3 METHOXYPHENYL)ETHYL]PHENOL; 3 [2 [4 (DIMETHYLAMINO)PHENYL]ETHYL] 5 METHOXYPHENOL; 3 METHOXY 5 [2 (4 METHOXYPHENYL)ETHYL]PHENOL; 4 (3,5 DIMETHOXYBENZYL) 2 METHOXYPHENOL; 4 [2 (3,5 DIMETHOXYPHENYL)ETHYL] 1 ETHOXY 2 METHOXYBENZENE; 4 [3 (1,3 BENZODIOXOL 5 YL)PROPYL]PHENOL; 4 [3 (3 HYDROXY 5 METHOXYPHENYL)PROPYL] 2 METHOXYPHENOL; 4 [3 (4 METHOXYPHENYL)PROPYL]PHENOL; BENZYL PHENYL ETHER; CALCIUM CALMODULIN DEPENDENT PROTEIN KINASE; CALMODULIN INHIBITOR; CHLORPROMAZINE; DIPHENYLETHANE; DIPHENYLMETHANE; GIGANTOL DERIVATIVE; N [4 [2 (3,5 DIMETHOXYPHENYL)ETHYL]PHENYL] N,N DIMETHYLAMINE; PHOSPHODIESTERASE I; TRIFLUOPERAZINE; UNCLASSIFIED DRUG; ANTIDEPRESSANT AGENT; ANTINEOPLASTIC AGENT; BIBENZYL DERIVATIVE; BIPHENYL DERIVATIVE; CALMODULIN; CHOLINERGIC RECEPTOR BLOCKING AGENT; CYCLIC NUCLEOTIDE PHOSPHODIESTERASE 1; GIGANTOL; GUAIACOL; LOCAL ANESTHETIC AGENT; NEUROLEPTIC AGENT; PROTEIN BINDING;

ARTICLE; DRUG SYNTHESIS; FLUORESCENCE; IC 50; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; GENETIC PROCEDURES; HUMAN; SYNTHESIS;

ANESTHETICS, LOCAL; ANTIDEPRESSIVE AGENTS; ANTINEOPLASTIC AGENTS; ANTIPSYCHOTIC AGENTS; BIBENZYLS; BIOSENSING TECHNIQUES; BIPHENYL COMPOUNDS; CALMODULIN; CHLORPROMAZINE; CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 1; GUAIACOL; HUMANS; MOLECULAR DOCKING SIMULATION; PARASYMPATHOLYTICS; PROTEIN BINDING; TRIFLUOPERAZINE;

EID: 79957476598     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.03.057     Document Type: Article

References (21)

1. S. Estrada, A. Rojas, Y. Mathison, A. Israel, and R. Mata Nitric oxide/cGMP mediates the spasmolytic action of 3,4′-dihydroxy-5,5′- dimethoxybibenzyl from scaphyglottis livida Planta Med. 65 1999 109 114 (Pubitemid 29138140)
2. M. Deciga-Campos, J.F. Palacios-Espinosa, A. Reyes-Ramirez, and R. Mata Antinociceptive and anti-inflammatory effects of compounds isolated from Scaphyglottis livida and Maxillaria densa J. Ethnopharmacol 114 2007 161 168 (Pubitemid 47539817)
3. S. Estrada-Soto, J.J. Lopez-Guerrero, R. Villalobos-Molina, and R. Mata Endothelium-independent relaxation of aorta rings by two stilbenoids from the orchids Scaphyglottis livida Fitoterapia 77 2006 236 239 (Pubitemid 44382510)
4. Y. Hernandez-Romero, L. Acevedo, M.D. Sanchez, W.T. Shier, H.K. Abbas, and R. Mata Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum J. Agr Food Chem. 53 2005 6276 6280 (Pubitemid 41169373)
5. Y. Hernandez-Romero, J.I. Rojas, R. Castillo, A. Rojas, and R. Mata Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii J. Nat. Prod. 67 2004 160 167 (Pubitemid 38282902)
6. W.Y. Cheung Calmodulin plays a pivotal role in cellular-regulation Science 207 1980 19 27 (Pubitemid 10142296)
7. I. Kovesi, D.K. Menyhard, M. Laberge, and J. Fidy Interaction of antagonists with calmodulin: insights from molecular dynamics simulations J. Med. Chem. 51 2008 3081 3093 (Pubitemid 351821869)
8. P.L. Majumder, S. Pal, and S. Majumder Dimeric phenanthrenes from the orchid Bulbophyllum reptans Phytochemistry 50 1999 891 897 (Pubitemid 29135056)
9. F. Orsini, L. Verotta, M. Lecchi, R. Restano, G. Curia, E. Redaelli, and E. Wanke Resveratrol derivatives and their role as potassium channels modulators J. Nat. Prod. 67 2004 421 426 (Pubitemid 38405706)
10. L.S. Hart, and C.R. Waddington Aromatic Rearrangements in the benzene series 4. Intramolecularity of both the ortho-rearrangement and para-rearrangement of benzyl phenyl ether as shown by labeling experiments J Chem Soc Perk T 2 1985 1607 1612
11. X. Yang, W. Wang, J. Tan, D. Song, M. Li, D. Liu, Y. Jing, and L. Zhao Synthesis of a series of novel dihydroartemisinin derivatives containing a substituted chalcone with greater cytotoxic effects in leukemia cells Bioorg. Med. Chem. Lett. 19 2009 4385 4388
12. B. Rivero-Cruz, I. Rivero-Cruz, R. Rodriguez-Sotres, and R. Mata Effect of natural and synthetic benzyl benzoates on calmodulin Phytochemistry 68 2007 1147 1155 (Pubitemid 46528462)
13. S. Martinez-Luis, A. Perez-Vasquez, and R. Mata Natural products with calmodulin inhibitor properties Phytochemistry 68 2007 1882 1903 (Pubitemid 47030615)
14. M. Gonzalez-Andrade, M. Figueroa, R. Rodriguez-Sotres, R. Mata, and A. Sosa-Peinado An alternative assay to discover potential calmodulin inhibitors using a human fluorophore-labeled CaM protein Anal. Biochem. 387 2009 64 70
15. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662 (Pubitemid 128590223)
16. R. Huey, G.M. Morris, A.J. Olson, and D.S. Goodsell A semiempirical free energy force field with charge-based desolvation J. Comput. Chem. 28 2007 1145 1152 (Pubitemid 46506716)
17. M. Vandonselaar, R.A. Hickie, J.W. Quail, and L.T. Delbaere Trifluoperazine-induced conformational change in Ca(2+)-calmodulin Nat. Struct. Biol. 1 1994 795 801
18. V. Harmat, Z. Bocskei, G. Naray-Szabo, I. Bata, A.S. Csutor, I. Hermecz, P. Aranyi, B. Szabo, K. Liliom, B.G. Vertessy, and J. Ovadi A new potent calmodulin antagonist with arylalkylamine structure: crystallographic, spectroscopic and functional studies J. Mol. Biol. 297 2000 747 755
19. Y. Hernandez-Romero, L. Acevedo, L. Sanchez Mde, W.T. Shier, H.K. Abbas, and R. Mata Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum J. Agric. Food Chem. 53 2005 6276 6280 (Pubitemid 41169373)
20. S. Suzuki, K. Ohno, T. Santa, and K. Imai Study on interactions of endocrine disruptors with estrogen receptor-beta using fluorescence polarization Anal. Sci. 19 2003 1103 1108
21. W.J. Wedemeyer, and D. Baker Efficient minimization of angle-dependent potentials for polypeptides in internal coordinates Proteins 53 2003 262 272 (Pubitemid 37193821)