Solubilization and Stabilization of the Cytotoxic Agent Coralyne

Cho, M.J.; Repta, A.J.; Cheng, C. C.; Zee-Cheng, Kwang Yuen; Higuchi, Takeru; Pitman, Ian H.

doi:10.1002/jps.2600641116

Cited by 22 publications

(5 citation statements)

References 7 publications

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“…145 A more detailed analysis by Taira et al 148 showed that the aggregation of DNA caused by coralyne was due to stacking arrangement of aggregated coralyne along the DNA phosphate backbone. As coralyne exhibits a high tendency for aggregation in aqueous buffers, [147][148][149] even at low concentrations the data is confusing and need to be interpreted with caution. In all earlier experiments aggregates of coralyne molecules were used rather than separate monomeric molecules which may have significant influence on optical properties of the complex formation.…”

Section: B Coralyne-b-dna Interactionmentioning

confidence: 94%

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Maiti

Kumar

2006

Medicinal Research Reviews

164

103

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Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-beta-d-glucoside of the aristolochia group have potential to form molecular complexes with nucleic acid structures and have attracted recent attention for their prospective clinical and pharmacological utility. This review highlights (i) the physicochemical properties of these alkaloids under various environmental conditions, (ii) the structure and functional aspects of various forms of deoxyribonucleic acid (DNA) (B-form, Z-form, H(L)-form, protonated form, and triple helical form) and ribonucleic acid (RNA) (A-form, protonated form, and triple helical form), and (iii) the interaction of these alkaloids with various polymorphic DNA and RNA structures reported by several research groups employing various analytical techniques like absorbance, fluorescence, circular dichroism, and NMR spectroscopy; electrospray ionization mass spectrometry, thermal melting, viscosity, and DNase footprinting as well as molecular modeling and thermodynamic studies to provide detailed binding mechanism at the molecular level for structure-activity relationship. Nucleic acids binding properties of these alkaloids are interpreted in relation to their biological activity.

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Section: B Coralyne-b-dna Interactionmentioning

confidence: 94%

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Maiti

Kumar

2006

Medicinal Research Reviews

164

103

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“…The water‐induced decomposition at pH > 12 may be a ring opening. Reversible addition of OH − followed by ring opening has been reported for coralyne (37).…”

Section: Resultsmentioning

confidence: 91%

“…The most efficient photooxidation is achieved at pH 12 ( Φ ox = 0.01). Coralyne is unstable above pH 12 due to the conversion to 6′‐acetylpapaverine in a reversible process (37). The first step of this reaction is addition of OH − at the 8th position (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Photooxidation of Alkaloids: Considerable Quantum Yield Enhancement by Rose Bengal‐sensitized Singlet Molecular Oxygen Generation

Görner¹,

Miskolczy

Megyesi

et al. 2011

Photochem & Photobiology

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The photooxidation of sanguinarine, coralyne and berberine was studied in oxygenated alkaline methanol solutions. Rose bengal as photosensitizer significantly accelerates the process, indicating the importance of singlet molecular oxygen in the reaction mechanism. The quantum yield of sensitized oxidation was found to increase significantly with pH and reaches 0.4 for berberine at pH 13.8. The direct oxidation of alkaloids is less efficient, the quantum yield does not exceed 0.01 even in oxygen-saturated solutions. The photoinduced electron ejection does not play a role in the oxidation. The uncharged pseudobase forms, which are present in alkaline medium, are oxidized much more easily than the alkaloid cations.

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“…Amphotericin B was dissolved according to the manufacturer's directions to form colloidal solutions, which were filtered through membranes of different porosity (1189). Kinetic studies were carried out on the hydrolysis and photochemical degradation of the cytotoxic agent coralyne (1190). Kinetic studies were carried out on the hydrolysis and photochemical degradation of the cytotoxic agent coralyne (1190).…”

Section: Pharmaceutical Aspectsmentioning

confidence: 99%

Pharmaceutical Sciences—1975: Literature Review of Pharmaceutics II∆∆Editor’s note: Part I of this article appeared in the July 1976 issue of the Journal of Pharmaceutical Sciences

Goodhart¹,

Eichman

1976

Journal of Pharmaceutical Sciences

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Solubilization and Stabilization of the Cytotoxic Agent Coralyne

Cited by 22 publications

References 7 publications

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives

Photooxidation of Alkaloids: Considerable Quantum Yield Enhancement by Rose Bengal‐sensitized Singlet Molecular Oxygen Generation

Pharmaceutical Sciences—1975: Literature Review of Pharmaceutics II∆∆Editor’s note: Part I of this article appeared in the July 1976 issue of the Journal of Pharmaceutical Sciences

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