On the chiroptical behavior of conjugated multichromophoric compounds of a new pseudoaromatic class: Bicolchicides and biisocolchicides

PLoS ONE

Volumn 5, Issue 5, 2010, Pages

  Funaioli, Tiziana ^a   Cavazza, Marino ^a   Zandomeneghi, Maurizio ^a   Pietra, Francesco ^b  

^a UNIVERSITY OF PISA   (Italy)

^b Accademia Lucchese di Scienze   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

10,10' BICOLCHICIDE DERIVATIVE; 9,9' BIISOCOLCHICIDE DERIVATIVE; AROMATIC COMPOUND; COLCHICIDE; ISOCOLCHICIDE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHROMATOPHORE; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; COLCHICINE; HYDROCARBONS, AROMATIC; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; TEMPERATURE;

EID: 77956511535     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0010617     Document Type: Article

References (36)

1. Harada N, Nakanishi K (1983) Circular dichroic spectroscopy. Exciton coupling in organic stereochemistry. University Science Books: California.
2. Berova N, Di Bari L, Pescitelli G (2007) Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 36: 914-931.
3. DeVoe H (1964) Optical properties of molecular aggregates. I. Classical model of electronic absorption and refraction. J Chem Phys 41: 393-400.
4. DeVoe H (1965) Optical properties of molecular aggregates.II. Classical theory of the refraction, absorption and optical activity of solutions and crystals. J Chem Phys 43: 3199-3208.
5. Frenkel J (1931) On the transformation of light into heat in solids. J Phys Rev 37: 17-44.
6. Superchi S, Giorgio E, Rosini C (2004) Structural determinations by circular dichroism. Spectra analysis using coupled oscillator methods: an update of the applications of the DeVoe polarizability model. Chirality 16: 422-451.
7. Zandomeneghi M (1979) Circular dichroism of an alkylbenzene. A coupled oscillator approach. J Phys Chem 83: 2926-2928.
8. Gawronski J, Skowronek P (2004) New chromophores for organic stereochemical analysis by exciton-coupled circular dichroism. Current Organic Chemistry 8: 65-82.
9. Semmelhack MF, Helquist PM, Jones LD (1971) Synthesis with zerovalent nickel. Coupling of aryl halides with bis(1,5-cyclooctadiene) nickel(0). J Am Chem Soc 93: 5908-5910.
10. Cavazza M, Pietra F (1997) A general entry to 10-halocolchicides and 9-haloisocolchicides. Synthetic Commun 27: 3405-3413.
11. Danieli B, Lesma G, Palmisano G, Riva R (1985) The structure elucidation of pseudothiocolchicine. Helv Chim Acta 68: 2173-2176.
12. Cavazza M, Zandomeneghi M, Pietra F (2000) Isolation of atropisomers in both the isocolchicide and colchicine series of alkaloids and determination of their chiroptical properties. Tetrahedron Lett 41: 9129-9133.
13. Gaffield W, Lundin RE, Horowitz RM (1984) Conformational isomerism and its relation to the mutarotation of isocolchicine. Chem Commun. pp 610-612.
14. Venables DS, Schmuttenmaer CA (1998) Far-infrared spectra and associated dynamics in acetonitrile-water mixtures measured with femtosecond THz pulse spectrometry. J Chem Phys 108: 4935-4944.
15. Kuyper LF, Hunter RN, Ashton D, Merz KM, Kollman PA (1991) Free energy calculations on the relative solvation free energies of benzene, anisole, and 1,2,3-trimethoxybenzene: theoretical and experimental analysis of aromatic methoxy solvation. J Phys Chem 95: 6661-6666.
16. Rapoport H, Lavigne JB (1956) The mutarotation of isocolchicine. J Am Chem Soc 78: 2455-2459.
17. Pietra F (2007) Why colchicine does not show mutarotation. With M05-2X density functional in the realm of tricky natural products. J Phys Org Chem 20: 1102-1107.
18. Gilbert K (2006) A steric energy minimization software. Revision GMMX, Global MMX Serena Software: Bloomington, IN; http://www.serenasoft.com.
19. Bushnell JE (2004-2007) Xanneal, Version 0.7.2; University of California, Santa Barbara, CA; http://bowers.chem.ucsb.edu/computing/index.shtml.
20. Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2: 364-382.
21. Lessinger L, Margulis TN (1978) The crystal structure of colchicine. A new application of magic integers to multiple-solution direct methods. Acta Cryst B34: 578-584.
22. Lessinger L, Margulis TN (1978) The crystal structure of isocolchicine, an inactive isomer of the mitotic spindle inhibitor colchicine. Acta Cryst B34: 1556-1561.
23. Veracini CA, Pietra F (1972) Molecular structure of tropone from its 1H nuclear magnetic resonance spectrum in a nematic solvent. J Chem Soc Chem Commun. pp 1262-1263.
24. Goerigk L, Grimme S (2009) Calculation of electronic circular dichroism spectra with time-dependent double-hybrid density functional theory. J Phys Chem A 113: 767-776.
25. Bruhn T, Hemberger Y, Schaumlöffel A, Bringmann G (2009) SpecDis version 1.45, University of Wuerzburg, Germany; http://www-organik.chemie.uniwuerzburg.de/lehrstuehlearbeitskreise/bringmann/specdis.
26. Klamt A, Jonas V (1996) Treatment of the outlying charge in continuum solvation models. J Chem Phys 105: 9972-9981.
27. Caricato M, Mennucci B, Tomasi J, Ingrosso F, Cammi R, et al. (2006) Formation and relaxation of excited states in solution: a new time dependent polarizable continuum model based on time dependent density functional theory. J Chem Phys 124: 124520-124533.
28. Cramer CJ, Truhlar DG (2008) A universal approach to solution modeling. Acc Chem Res 41: 760-768.
29. Florián J, Warshel A (1999) Calculations of hydration entropies of hydrophobic, polar, and ionic solutes in the framework of the Langevin dipoles solvation model. J Phys Chem B 103: 10282-10288.
30. Kendall RA, Apra E, Bernholdt DE, Bylaska EJ, Dupuis M, et al. (2000) High performance computational chemistry: an overview of NWChem a distributed parallel application. Comp Physics Comm. 128: 260-283.
31. Kühne TD, Krack M, Mohamed F, Parrinello M (2007) Efficient and accurate Car-Parrinello-like approach to Born-Oppenheimer molecular dynamics. Phys Rev Lett 98: 066401.
32. Major DT, Gao J (2006) A combined quantum mechanical and molecular mechanical study of the reaction mechanism and a-amino acidity in alanine racemase. J Am Chem Soc 128: 16345-16357.
33. Case DA, Darden TA, Cheatham TE, Simmerling CL, Wang J, et al. (2008) AMBER 10; University of California, San Francisco, CA; http://ambermd.org.
34. Elstner M, Porezag D, Jungnickel G, Elsner J, Haugk M, et al. (1998) Selfconsistent-charge density-functional tight-binding method for simulations of complex materials properties. Phys Rev B 58: 7260-7268.
35. Crawford TD, Tam MC, Abrams ML (2007) The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra. J Phys Chem 111: 12057-12068.
36. Petrenko T, Neese F (2007) Analysis and prediction of absorption band shapes, fluorescence band shapes, resonances Raman intensities and excitation profiles using the time-dependent theory of electronic spectroscopy. J Chem Phys 127: 164319.