Synthesis and fluorescence investigation of differently substituted Benzo[b][1,8]Naphthyridines: Interaction with different solvents and bovine serum albumin (BSA)

Journal of Fluorescence

Volumn 21, Issue 3, 2011, Pages 1033-1047

  Shelar, Deepak P ^a   Patil, Sandeep R ^a   Rote, Ramhari V ^a   Toche, Raghunath B ^a   Jachak, Madhukar N ^a  

^a K T H M COLLEGE   (India)

Author keywords

Bovine serum albumin (BSA); Fluorophore; HOMO LUMO; Phosphate buffer; Solvatochromic effect

Indexed keywords

BASIC MEDIUM; BOVINE SERUM ALBUMINS; DIFFERENT SOLVENTS; ELECTRON DONOR ACCEPTORS; FLUORESCENCE PROPERTIES; HOMO- LUMO; PHOSPHATE BUFFER; PHOSPHATE BUFFERS; REPRESENTATIVE COMPOUND; SOLVATOCHROMIC EFFECTS; SPECTROSCOPIC PROPERTY;

FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; ORGANIC SOLVENTS; QUANTUM YIELD;

BODY FLUIDS;

BENZO(B)1,5 NAPHTHYRIDINE; BENZO(B)1,5-NAPHTHYRIDINE; BOVINE SERUM ALBUMIN; NAPHTHYRIDINE DERIVATIVE; SOLVENT;

ANIMAL; CHEMISTRY; CONFERENCE PAPER; FLUORESCENCE; METHODOLOGY; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; FLUORESCENCE; NAPHTHYRIDINES; SERUM ALBUMIN, BOVINE; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

BOVINAE;

EID: 80052571867     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-010-0783-1     Document Type: Conference Paper

References (76)

1. Meijere A de (1998) In topics in current chemistry, carbon-rich compounds, I, (Ed.) Springer, Berlin, Germany, vol 196
2. Meijere A de (1999) In topics in current chemistry, carbon-rich compounds, II, (Ed.) Springer, Berlin, Germany, vol 201
3. Diederich F, Stang PJ, Tykwinski RR (2005) In acetylene chemistry: chemistry, biology and material science, (Eds.) Wiley-VCH, Weinheim, Germany
4. Haley MM, Tykwinski RR (2006) In carbon-rich compounds: from molecules to materials, (Eds.) Wiely-VCH, Weinheim, Germany
5. Mullen K, Scherf U (2006) In organic light emitting devices: synthesis properties and applications (Eds.): Wiely-VCH, Weinheim, Germany
6. Chen J, Reed MA, Dirk SM, Price DW, Rawlett AM, Tour JM, Grubisha DS, Bennett DW (2003) In NATO science series II, mathematics, physics, chemistry (Molecular Electronics: Bio- Sensors and Bio-Computers) (Eds.): Plenum, New York, Vol. 96: pp 59-195
7. Domerco B, Hreha RD, Zhang YD, Haldi A, Barlow S, Marder SR, Kippelen B (2003) Organic light-emitting diodes with multiple photocrosslinkable hole-transport layers. J Polym Sci Part B: Polym Phys 41(21):2726-2732
8. Shirota Y (2000) Organic materials for electronic and optoelectronic devices. J Mater Chem 10:1-25
9. Schwab PFH, Levin MD, Michl J (1999) Molecular rods. 1. Simple axial rods. Chem Rev 99:1863-1933 (Pubitemid 129585164)
10. Mullen K, Wehner G (1998) In electronic materials: the oligomer approach, (Eds.) Wiely-VCH, Weinheim, Germany
11. Nalwa HS, Miyata S (1997) In nonlinear optics of organic molecules and polymers (Eds.) CRC Press, Boca Raton, FL
12. Kang H, Evrenenko G, Dutta P, Clays K, Song K, Marks TJ (2006) X-shaped electro-optic chromophore with remarkably blue-shifted optical absorption. synthesis, characterization, linear/ nonlinear optical properties, self-assembly, and thin film microstructural characteristics. J Am Chem Soc 128:6194-6205
13. Knox JE, Halls MD, Hratchian HP, Schlegel HB (2006) Chemical failure modes of Alq3-based OLEDs: Alq3 hydrolysis. Phys Chem Chem Phys 8:1371-1377
14. Shukla VK, Kumar S, Deva D (2006) Light induced effects on the morphology and optical properties of tris-(8-hydroxyquinoline) aluminium (Alq3) small molecular thin film. Synth Met 156:387-391
15. Seminario JM (2005) Molecular electronics: approaching reality. Nat Mater 4:111-113 (Pubitemid 40178704)
16. Hughes G, Bryce MR (2005) Electron-transporting materials for organic electroluminescent and electrophosphoresc-ent devices. J Mater Chem 15:94-107 (Pubitemid 40143746)
17. Van der Auweraer M, De Schryver FC (2004) Organic electronics: supra solutions. Nat Mater 3:507-508
18. Special Issue on Organic Electronics (2004) Chem Mater 16:4381-4846
19. Simpson CD, Wu J, Watson MD, Müllen K (2004) From graphite molecules to columnar superstructures-an excercise in nanoscience. J Mater Chem 14:494-504
20. Kapturkiewicz A, Herbich J, Nowacki J (1997) Highly efficient electrochemical generation of fluorescent intramolecular chargetransfer states. Chem Phys Lett 275:355
21. Herbich J, Kapturkiewicz A (1997) Electronic and molecular structure of charge transfer singlet states: 4-(9-anthryl)julolidine and 4-(9-acridyl) julolidine. Chem Phys Lett 273:8
22. Herbich J, Kapturkiewicz A, Nowacki J (1996) Phosphorescent intramolecular charge transfer triplet states. Chem Phys Lett 262:633
23. 2-DMPP. Acta Phys Polon A 95:321
24. Miyasaka H, Itaya A, Rotkiewicz K, Rechthaler K (1999) Picosecond laser photolysis studies of DMA-DMPP in solution. Chem Phys Lett 307:121
25. Piorun D, Parusel ABJ, Rechthaler K, Rotkiewicz K, Köhler G (1999) Acid-base properties of bis-pyrazolopyridine derivatives in nonaqueous solutions. J Photochem Photobiol A:Chem 129:33
26. Parusel ABJ, Rechthaler K, Piorun D, Danel A, Khatchatryan K, Rotkiewicz K, Köhler G (1998) Fluorescence properties of donor- acceptor-substituted pyrazoloquinolines. J Fluoresc 8:375
27. Khatchatryan K, Rotkiewicz K, Köhler G, Danel A, Tomasik P, Khatchatryan K (1997) Emissive properties and intramolecular charge transfer of pyrazoloquinoline derivatives. J Fluoresc 7:301
28. Rotkiewicz K, Rechthaler K, Puchala A, Rasala D, Styrcz S, Köhler G (1996) Dual fluorescence and intramolecular charge transfer in a bulky electron donor-acceptor system. N, N-Dimethylanilino- bis-pyrazolopyridine. J Photochem Photobiol A: Chem 98:15-19 (Pubitemid 126168684)
29. Parusel ABJ, Schamschule R, Köhler G (1998) Theoretical description of solvent effects on fluorescence spectra of bulky charge transfer compound DMA-DMPP. J Comput Chem 19:1584
30. Parusel ABJ, Schamschule R, Köhler G (1997) A semiempirical study of the fluorescence properties of large charge-transfer compounds. N, N-dimethylanilino-bis-pyrazolopyridine. Ber Bunsenges Phys Chem 101:1836-1843 (Pubitemid 127745974)
31. Parusel ABJ, Schamschule R, Piorun D, Rechthaler K, Puchala A, Rasala D, Rotkiewicz K, Köhler G (1997) Semiempirical characterization of substituted bis-pyrazolopyridines as new bulky electron donor-acceptor systems in their electronic ground state. J Mol Struct (Theochem) 419:63-76
32. Singh AK, Kanvah S (2000) Effect of micro heterogeneous media on fluorescence and fluorescence probe properties of diarylpolyenes. New J Chem 24:639-646 (Pubitemid 30649142)
33. Singh AK, Manjula D, Kanvah S (2000) α,ω-diphenylpolyenes cabable of exhibiting twisted intramolecular charge transfer fluorescence: a fluorescence and fluorescence probe study of nitro- and nitrocyano-substituted 1, 4-diphenyl butadienes. J Phys Chem A 104:464-471 (Pubitemid 33638761)
34. Singh AK, Krishna TSR (1997) Photophysical and optical probe properties of 1-(p-N, N-Dimethylaminophenyl)-4-Phenyl-2-Methyl- 1E, 3E-Butadiene. J Photosci 4:1-5
35. Singh AK, Darshi M (2004) A fluorescence study of (4-{(1E, 3E)- 4-[4-(dimethyl-amino)phenyl]- buta-1, 3-dienyl}phenyl)methanol and its bioconjugates with bovine and human serum albumins. New J Chem 28:120-126 (Pubitemid 38223582)
36. Caluwe P (1980) Heteroannelations with o-aminoaldehydes. Tetrahedron 36:2359
37. Fehnel EA (1966) Friedländer syntheses with o-aminoaryl ketones. I. Acid-catalyzed condensations of o-aminobenzophenone with ketones. J Org Chem 31:2899
38. Boekelheide V, Nottke JE (1969) Novel cyclization reaction of acetylene derivatives. J Org Chem 34(12):4134-4136
39. Liao TK, Nyberg WH, Cheng CC (1971) Total synthesis of camptotheein. I. Synthesis of ethyl 8-(α-chlorobutyryloxymethyl)- 7,9-dioxo-7,8,9,11- tetrahydro indolizino [1,2-a]quinoline-8-carboxylate and related tetracyclic compounds. J Heterocyclic Chem 8:373
40. Zalkow LH, Nabors JB, French K, Bisarya SC (1971) Studies in the synthesis of Camptothecin. An efficient synthesis of 2,3-dihydro-1Hpyrazolo[ 3,4-b]quinoline. J Chem Soc (C):3551-3554.
41. Borch RF, Grudzinskas CV, Peterson DA, Weber LD (1972) New synthesis of substituted 2(1 H)-pyridones. Synthesis of a potential camptothecin intermediate. J Org Chem 37(8):1141-1145
42. Croisy A, Jacqquignon P, Fravolini A (1974) Sur quelques analogues fluores des [1] benzothiopyrano[4, 3-b]indoles et des 6 H[1] benzothiopyrano[4, 3-b]quinoleines. J Heterocyclic Chem 11:113
43. Cliff GR, Jones G, Woollard J McK (1974) Intramolecular nitrene insertions into aromatic and heteroaromatic systems. Part II. Insertions into thiophen rings. J Chem Soc Perkin I:2072-2076
44. Sugasawa T, Toyoda T, Sasakura K (1974) Experiments on the synthesis of dl-camptothecin. III. Total synthesis of dl-camptothecin. Chem Pharm Bull 22:771-781
45. Tang CSF, Morrow CJ, Rapoport H (1975) Total synthesis of dl-camptothecin. J Am Chem Soc 97:159
46. Da SA, Primofiore G, Livo O, Ferrarini PL, Spinelli S (1979) Synthesis of some 3-substituted quino[3, 2-c][1, 8]naphtyridines. A new heterocyclic ring system. J Heterocyclic Chem 16:169
47. Hawes EM, Wibberley DG (1966) 1,8-Naphthyridines. J Chem Soc:315-321
48. Majewicz TG, Caluwe P (1975) Chemistry of o-aminoaldehydes. Reactions of 2-aminonicotinaldehyde and cyclohexanediones. J Org Chem 40(23):3407-3410
49. Hawes EM, Wibberley DG (1967) 1,8-Naphthyridines. Part II. Preparation and some reactions of 2-substituted derivatives. J Chem Soc (C):1564-1568.
50. Hawes EM, Gorecki DKJ, Gedir RG (1977) 2, 3-Disubstituted 1, 8-naphthyridines as potential diuretic agents. 2. 5, 7-Dimethyl derivatives. J Med Chem 20(6):838-841 (Pubitemid 8096818)
51. Haufel J, Breitmaier E (1974) Synthesis of pyrazolo heteroaromatic compounds by means of 5-amino-3-methyl-1-phenylpyrazole- 4-carbaldehyde. Angew Chem Internat Edit 13(9):604
52. Simay A, Takacs K, Toth L (1982) Aminopyrazoles, II. Synthesis of pyrazolo[3, 4-b] pyridines via Vilsmeier-Haack reaction of 5- acetaminopyrazoles. Acta Chim Acad Sci Hung 109:175-187
53. Ahluwalia VK, Dahiya A (1996) Synthesis of pyrazolo[3', 4': 5, 6]pyrido[2, 3-d] pyrimidines. Indian J Chemistry 35B:1208-1210
54. Ahluwalia VK, Dahiya A, Garg VK (1997) Reaction of 5- amino- 4-formyl-3-methyl (or phenyl)-1-phenyl-1 H-prazoles with compounds containing active methylene group: synthesis of fused heterocyclic rings. Indian J Chemistry 36B:88-90
55. Godard A, Queguiner G (1980) Sur les orthoamino formyl quinoleines, nouveaux synthons heterocycliques. J Heterocyclic Chem 17:465
56. Godard A, Queguiner G (1982) Synthesis of Benzonaphthyridines. J Heterocyclic Chem 19:1279
57. Jachak MN, Avhale AB, Tantak CD, Toche RB (2005) Friedländer condensation of 5-Aminopyrazole-4-carbaldehydes with reactive a-methylene ketones: synthesis of pyrazolo[3, 4-b] pyridines. J Heterocyclic Chem 42:1311-1319
58. Jachak MN, Avhale AB, Tantak CD, Toche RB (2006) A convenient route for the synthesis of pyrazolo[3, 4-d]pyrimidine, pyrazolo[3, 4-b][1, 6]naphthyridine and pyrazolo[3, 4-b]quinoline derivatives. J Heterocyclic Chem 43:1169-1175
59. Jachak MN, Avhale AB, Toche RB, Sabnis RW (2007) Synthesis of pyrazolo-annelated heterocyclic ring compounds such as pyrazolo[3, 4-b]pyridines and pyrazolo[4', 3':5, 6]-pyrido[2, 3-d] pyrimidines. J Heterocyclic Chem 44:343-347 (Pubitemid 350205232)
60. Jachak MN, Bagul SM, Kazi MA, Toche RB (2009) Facile synthesis of novel pyrazolo[3, 4-h][1, 6]naphthyridines derivatives from new 4-amino-pyrazolo[3, 4-b] pyridine-5- carbaldehyde. J Heterocyclic Chem 46:343
61. Toche RB, Bhavsar DC, Kazi MA, Bagul SM, Jachak MN (2010) Synthesis of pyrazolopyridine 3-carboxylates by Friedlander condensation. J Heterocyclic Chem 47:287-291
62. Shelar DP, Birari DR, Rote RV, Patil SR, Toche RB, Jachak MN (2010) Novel Synthesis of 2-aminoquinoline-3-carbaldehyde, benzo[b][1, 8] naphthyridines and study of their fluorescence behavior. J Phys Org Chem. doi:10.1002/poc.1727
63. Peters T (1985) Serum albumin. Jr Advan Prot Chem 37:161-245
64. Zollinger H (2003) Color Chemistry, 3rd ed., Switzerland, Page No.479
65. Stewart JJP (1990) J Comput-Aided Mol Des 4:1
66. Stewart JJP. QCPE Bull. (1989), 9, 10. QCPE program no. 455
67. Perov AN (1980) Energy of intermediate pair interactions as a characteristics of their nature. Theory of the solvate (Fluoro) Chromism of three-component solutions. Opt Spectrosc 49:371-374
68. Neporent BS, Bakhshiev NG (1960) On the role of universal and specific intermolecular interactions in the influence of the solvent on the electronic spectra of molecules. Opt Spectrosc 8:408-413
69. Dey JK, Warner IM (1998) Charge-transfer effects on the fluorescence spectra of 9-aminocamptothecin steady-state and time-resolved fluorescence studies. J Photochem Photobiol A: Chem 116:27
70. Biswas A, Dey JK (2001) Ground and excited state ionization behavior of 9-aminocamptothecin: an absorption and fluorescence study. Indian J Chem 40A:1143-1148 (Pubitemid 33127099)
71. Lakowicz JR (1999) In principals of fluorescence spectroscopy, 2nd ed., New York
72. Fletecher AN (1969) Quinine sulfate as a fluorescence quantum yield standard. Phot Chem Photo Biol 9(5):439-444
73. Eastman JW (1967) Quantitative spectrofluorimetry-the fluorescence quantum yield of quinine sulfate. Photo Chem Photo Biol 6 (1):55-72
74. Adams MJ, Highfield JG, Kirkbright GF (1977) Determination of absolute fluorescence quantum efficiency of quinine bisulfate in aqueous medium by optoacoustic spectrometry. Anal Chem 49 (12):1850-1852
75. Meech SR, Phillips D (1983) Photophysics of some common fluorescence standards. J Photochem 23:193-217
76. Papadopoulou A, Green RJ, Frazier A (2005) Interaction of flavonoids with bovine serum albumin: a fluorescence quenching study. J Agric Food Chem 53:158-163 (Pubitemid 40066484)