Molecular organization of the antifungal and anticancer drug 2-(2,4-dihydroxyphenylo)-5,6-dichlorobenzothiazole (dHBBT) in solution and in lipid membranes studied by means of electronic absorption spectroscopy

Journal of Photochemistry and Photobiology B: Biology

Volumn 76, Issue 1-3, 2004, Pages 33-40

  Gagoś, Mariusz ^a   Niewiadomy, Andrzej ^a   Gruszecki, Wiesław I ^b  

^a UNIVERSITY OF LIFE SCIENCES IN LUBLIN   (Poland)

^b MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

2 (2,4 Dihydroxyphenylo) 5,6 dichlorobenzothiazole; Exciton splitting; Lipid membranes; Molecular aggregates; Molecular dimers

Indexed keywords

2 (2,4 DIHDROXYPHENYLO) 5,6 DICHLOROBENZOTHIAZOLE; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; DIPALMITOYLPHOSPHATIDYLCHOLINE; LIPOSOME; MONOMER; ORGANIC SOLVENT; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; BILAYER MEMBRANE; CONTROLLED STUDY; DIMERIZATION; DRUG DETERMINATION; DRUG STRUCTURE; LINEAR DICHROISM; LIPID MEMBRANE; MOLECULAR DYNAMICS; MOLECULAR MODEL; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; THEORETICAL STUDY;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ANTIBIOTICS, ANTIFUNGAL; ANTINEOPLASTIC AGENTS; CIRCULAR DICHROISM; DIMERIZATION; DRUG CARRIERS; LIPID BILAYERS; LIPOSOMES; MODELS, BIOLOGICAL; MOLECULAR CONFORMATION; ORGANIC CHEMICALS; SOLVENTS; SPECTROPHOTOMETRY, ATOMIC; TEMPERATURE;

EID: 5644302515     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2004.07.002     Document Type: Article

References (16)

1. J. Matysiak A. Niewiadomy G. Macik-Niewiadomy T. Kornillowicz Dependence of fungistatic activity of 2,4-dihydroxythiobenzanilides on the structure and lipophilic nature of the compounds Eur. J. Med. Chem. 35 2000 393-404
2. P. Magdolen P. Zahradnik P. Foltinova Synthesis and antimicrobial activity of new 2-phenylethynylbenzothiazoles and related salts Arzneimittelforschung 50 2000 1023-1027
3. S.D. Paranjape A.S. Bobade B.G. Khadse Synthesis and evaluation of new triazolobenzothiazole derivatives as potential anti-tubercular agents Arzneimittelforschung 51 2001 916-919
4. H.M. el-Shaaer S.A. Abdel-Aziz H.A. Allimony U.F. Ali R.M. Abdel-Rahman Synthesis and antimicrobial activities of some new 2-substituted benzoxazole/benzothiazole derivatives Pharmazie 52 1997 585-589
5. T.D. Bradshaw S. Wrigley D.F. Shi R.J. Schultz K.D. Paull M.F. Stevens 2-(4-Aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity Br. J. Cancer 77 1998 745-752
6. E. Kashiyama I. Hutchinson M.S. Chua S.F. Stinson L.R. Phillips G. Kaur E.A. Sausville T.D. Bradshaw A.D. Westwell M.F. Stevens Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles J. Med. Chem. 42 1999 4172-4184
7. G. Wells T.D. Bradshaw P. Diana A. Seaton D.F. Shi A.D. Westwell M.F. Stevens Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives Bioorg. Med. Chem. Lett. 10 2000 513-515
8. D.F. Shi T.D. Bradshaw S. Wrigley C.J. McCall P. Lelieveld I. Fichtner M.F. Stevens Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo J. Med. Chem. 39 1996 3375-3384
9. A. Gaplovsky J. Donovalova P. Magdolen S. Toma P. Zahradnik Spectroscopic study of 2-[2-(4-cyclaminophenyl)ethen-1-yl] benzothiazoles and their N-allylbenzothiazolium bromides. Solvent and substituent effects on their ultraviolet-visible and fluorescence spectra Spectrochim. Acta A Mol. Biomol. Spectrosc. 58 2002 363-371
10. A.K. Dutta K. Ray T.N. Misra Aggregation induced reabsorption of 3-(2-benzothiazolyl)-7octadecyloxy coumarin molecules assembled in Langmuir-Blodget films: a fluorescence study Solid State Commun. 94 1995 53-59
11. M. Kasha Energy transfer mechanisms and the molecular exciton model for molecular aggregates Radiat. Res. 20 1963 55-70
12. J. Parkash J.H. Robblee J. Agnew E. Gibbs P. Collings R.F. Pasternack J.C. de Paula Depolarized resonance light scattering by porphyrin and chlorophyll a aggregates Biophys. J. 74 1998 2089-2099
13. A. Niewiadomy G. Grynkiewicz W. Szelejewski A. Kutner J. Ramza Derivatives of 2-(b-rezorcylo)-1,3-benzothiazol, the methods of synthesis and containing them pharmacological preparations (in Polish). 2002, Patent pending P-3555900s: Poland
14. W.I. Gruszecki J. Sielewiesiuk Orientation of xanthophylls in phosphatidylcholine multibilayers Biochim. Biophys. Acta 1023 1990 405-412
15. K. Fiksiński D. Fra̧ckowiak Comparison of various film used in biophysical investigations as anisotropic matrices Spectrosc. Lett. 13 1980 873-889
16. W.I. Gruszecki M. Gagos M. Herec Dimers of polyene antibiotic amphotericin B detected by means of fluorescence spectroscopy: molecular organization in solution and in lipid membranes J. Photochem. Photobiol. B: Biol. 69 2003 49-57