Fluorescence, circular dichroism, NMR, and docking studies of the interaction of the alkaloid malbrancheamide with calmodulin

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 26, Issue 3, 2011, Pages 378-385

  Figueroa, Mario ^a   González Andrade, Martín ^a   Sosa Peinado, Alejandro ^a   Madariaga Mazón, Abraham ^a   Del Río Portilla, Federico ^b   Del Carmen González, María ^a   Mata, Rachel ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b Institute of Chemistry   (Mexico)

Author keywords

calmodulin; circular dichroism; docking; fluorescence; Malbranchea aurantiaca; NMR titration

Indexed keywords

ALKALOID DERIVATIVE; AMIDE; CALMODULIN; CALMODULIN INHIBITOR; CHLORPROMAZINE; ISOMALBRANCHEAMIDE; ISOMALBRANCHEAMIDE B; PREMALBRANCHEAMIDE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSENSOR; CHLORINATION; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG ISOLATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FUNGUS; HYDROPHOBICITY; MALBRANCHEA AURANTIACA; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

ASCOMYCOTA; CALMODULIN; CIRCULAR DICHROISM; FLUORESCENCE; INDOLE ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

FUNGI; MALBRANCHEA AURANTIACA;

EID: 79955563956     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2010.518964     Document Type: Article

References (25)

1. Kuboniwa H, Tjandra N, Grzesiek S, Ren H, Klee CB, Bax A. Solution structure of calcium-free calmodulin. Nat Struct Biol 1995; 2:768-776.
2. Chattopadhyaya R, Meador WE, Means AR, Quiocho FA. Calmodulin structure refined at 1.7 Å resolution. J Mol Biol 1992; 228:1177-1192. (Pubitemid 23018499)
3. Gsponer J, Christodoulou J, Cavalli A, Bui JM, Richter B, Dobson CM, Vendruscolo M. A coupled equilibrium shift mechanism in calmodulin-mediated signal transduction. Structure 2008; 16: 736-746. (Pubitemid 351615020)
4. Cheung WY. Calmodulin plays a pivotal role in cellular regulation. Science 1980; 207:19-27. (Pubitemid 10142296)
5. Schwaller B.. Calcium-binding Proteins. In: Schwaller B, ed. Encyclopedia of Life Sciences. Chichester: John Wiley and Sons; 2005;1-8.
6. Klee CB, Crouch TH, Richman PG. Calmodulin. Annu Rev Biochem 1980; 49:489-515.
7. Karwatowska-Krynska E, Beresewicz A. Trifluoperazine protection of hypoxic myocardium. Pol J Pharmacol Pharm 1985; 37:615-627. (Pubitemid 16189429)
8. Porumb T, Yau P, Harvey TS, Ikura M. A calmodulin-target peptide hybrid molecule with unique calcium-binding properties. Protein Eng 1994; 7:109-115. (Pubitemid 24009869)
9. Douglass PM, Salins LL, Dikici E, Daunert S. Class-selective drug detection: fluorescently-labeled calmodulin as the biorecognition element for phenothiazines and tricyclic antidepressants. Bioconjug Chem 2002; 13:1186-1192. (Pubitemid 35420009)
10. Hennessey TM, Kung C. An anticalmodulin drug, W-7, inhibits the voltage-dependent calcium current in Paramecium caudatum. J Exp Biol 1984; 110:169-181. (Pubitemid 14059062)
11. Craven CJ, Whitehead B, Jones SK, Thulin E, Blackburn GM, Waltho JP. Complexes formed between calmodulin and the antagonists J-8 and TFP in solution. Biochemistry 1996;35:10287-10299. (Pubitemid 26277287)
12. Martínez-Luis S, Rodríguez R, Acevedo L, González M, Lira- Rocha A, Mata R. Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiaca. Tetrahedron 2006;62:1817-1822. (Pubitemid 43152081)
13. Figueroa M, Gonzalez M, Mata R. Malbrancheamide B, a novel compound from the fungus Malbranchea aurantiaca. Nat Prod Res 2008; 22:709-714. (Pubitemid 351943323)
14. Miller KA, Figueroa M, Valente MW, Greshock TJ, Mata R, Williams RM. Calmodulin inhibitory activity of the malbrancheamides and various analogs. Bioorg Med Chem Lett 2008; 18:6479-6481.
15. González-Andrade M, Figueroa M, Rodríguez-Sotres R, Mata R, Sosa-Peinado A. An alternative assay to discover potential calmodulin inhibitors using a human fluorophore-labeled CaM protein. Anal Biochem 2009; 387:64-70.
16. Rivero-Cruz B, Rivero-Cruz I, Rodríguez-Sotres R, Mata R. Effect of natural and synthetic benzyl benzoates on calmodulin. Phytochemistry 2007; 68:1147-1155. (Pubitemid 46528462)
17. Pérez-Iratxeta C, Andrade-Navarro MA. K2D2: estimation of protein secondary structure from circular dichroism spectra. BMC Struct Biol 2008; 8:25.
18. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK. Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J Comp Chem 1998;19:1639-1662. (Pubitemid 128590223)
19. Huey R, Morris GM, Olson AJ, Goodsell DS. A semiempirical free energy force field with charge-based desolvation. J Comput Chem 2007; 28:1145-1152. (Pubitemid 46506716)
20. Martínez-Luis S, Pérez-Vásquez A, Mata R. Natural products with calmodulin inhibitor properties. Phytochemistry 2007; 68:1882-1903. (Pubitemid 47030615)
21. Ding Y, Greshock TJ, Miller KA, Sherman DH, Williams RM. Premalbrancheamide: synthesis, isotopic labeling, biosynthetic incorporation, and detection in cultures of Malbranchea aurantiaca. Org Lett 2008; 10:4863-4866.
22. Mathur S, Badertscher M, Scott M, Zenobi R. Critical evaluation of mass spectrometric measurement of dissociation constants: accuracy and cross-validation against surface plasmon resonance and circular dichroism for the calmodulin-melittin system. Phys Chem Chem Phys 2007; 9:6187-6198.
23. Settimo L, Donnini S, Juffer AH, Woody RW, Marin O. Conformational changes upon calcium binding and phosphorylation in a synthetic fragment of calmodulin. Biopolymers 2007; 88: 373-385. (Pubitemid 46732422)
24. Harmat V, Böcskei Z, Náray-Szabó G, Bata I, Csutor AS, Hermecz I, Arányi P, Szabó B, Liliom K, Vértessy BG, Ovádi J. A new potent calmodulin antagonist with arylalkylamine structure: crystallographic, spectroscopic and functional studies. J Mol Biol 2000; 297:747-755.
25. Vandonselaar M, Hickie RA, Quail JW, Delbaere LT. Trifluoperazineinduced conformational change in Ca(2+)-calmodulin. Nat Struct Biol 1994; 1:795-801.