• Korean Journal of Microbiology
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• v.44 no.2
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• pp.110-115
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• 2008

Acridine was not a substrate for fungal laccase but it was oxidized to acridone in the culture medium of P. cinnabarinus SCH-3. During the cultivation of P. cinnabarinus SCH-3, Laccase was the predominant extracellular phenoloxidase, and 3-hydroxyanthranilic acid (3-HAA) was produced in the early culture. Cinnabarinic acid (CA) was observed to accumulate in the culture medium. When P. cinnabarinus was grown in the culture medium containing acridine, acridine was oxidized to acridone. But when the laccase purified from the culture medium of P. cinnabarinus directly reacted with acridine in sodium tartrate buffer (pH 3.0), The oxidation of acridine did not happen. In contrast, when 3-HAA was added to the buffer that was mixed with laccase and acridine, the acridine was oxidized to acridone. While in vitro studies, the CA was formed from 3-HAA in the presence of purified laccase. The results suggest that the acridine should be oxidized to the acridone through the mediation of 3-HAA by the laccase in the culture medium of P. cinnabarinus SCH-3.

• Natural Product Sciences
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• v.27 no.3
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• pp.183-186
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• 2021

A new acridone alkaloid, melixyloidin (1), and two known alkaloids (2-3) were isolated from Melicope xanthoxyloides (F. Muell) T.G. Hartley leaves. The structure of melixyloidin were elucidated using NMR spectra and high-resolution ESIMS data. Acridone alkaloids 1-3 were evaluated against MCF-7 and HeLa cells. 1,3,4-Trimethoxy-10-methylacridin-9-one (2) showed potent cytotoxic activity against MCF-7 cells with an IC₅₀ value of 5.31 μM.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1994.04a
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• pp.216-216
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• 1994

안트라싸이클린계 항암항생제의 부작용 발생기전으로는 C-고리의 퀴논 부위에 전자가 전달되어 퀴논고리가 환원되는 과정이 제시되고 있으며 그중 하나의 전자가 전달되어 생성되는 활성산소(activated oxygen)가 심장독성과 관련이 있는 것으로 알려져 있다. 이 때 퀴논고리의 환원력(전자흡수능력)이 C-고리 자체의 변환, 또는 인접 B-고리에 도입된 치환체의 영향으로 억제될 수 있다는 보고를 이론적 근거로 하여 안트라싸이클리논 골격을 전자흡수능력을 가진 acridone 골격으로 치환한 9-ethynyl-6,9-trihydroxy-7,8,9,10-tetrahydro-benzo〔b〕acridone을 합성하였으며 이를 daunosamine과 축합하기 위하여 $C_{7}$위치에 OH기를 도입한 화합물로 변환하였다.

• Archives of Pharmacal Research
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• v.21 no.4
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• pp.445-451
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• 1998

A series of 5-hydroxy-4-quinolone (3) and 5-methoxy-4-quinolone (4) derivatives were synthesized as truncated acridone analogues and evaluated for antitumor, antiheroes and antituberculosis activities. Among them 5-hydroxy-8-methoxy-quinolone showed potent antitumor activity ($IC_{50}$=17.7 $\mu\textrm{M}$ for HL60) which was greater than that of acronycine. However, these compounds didn't show any significant antiheroes or antituberculosis activity.

• Journal of Photoscience
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• v.9 no.2
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• pp.488-490
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• 2002

DNA photodamage mediated by photosensitizers are believed to play an important role in solar UVA carcinogenesis. We investigated the relationship between the DNA-damaging abilities of photoexcited xanthone analogues (as photosensitizers) and their highest occupied molecular orbital (HOMO) energies. DNA damage was examined using /sup 32/P-labeled DNA fragments obtained from the p53 tumor suppressor gene. These compounds induced DNA photodamage in a similar manner, and the extents of DNA damage were following order: xanthone> thioxanthone > acridone. Photoexcited xanthone caused nucleobase oxidation specifically at 5'-G of GG sequence in double-stranded DNA. An oxidative product of 2'-deoxyguanosine, 8-hydroxy-2'-deoxyguanosine (8-OHdG), was detected, and the amount was decreased by DNA denaturation. These findings suggest that photoexcited xanthone generates 8-OHdG at 5'-G of GG in double-stranded DNA through electron transfer. The calculated HOMO energies of these photosensitizers decreased in the following order: xanthone> thioxanthone > acridone. This study has demonstrated that DNA-damaging abilities of these photosensitizers increased exponentially with an increase in their HOMO energies.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1993.04a
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• pp.119-119
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• 1993

안트라싸이클린계 항암항생제의 부작용 발생기전으로는 C-고리의 퀴논 부위에 전자가 전달되어 퀴논 고리가 환원되는 과정이 제시되고 있으며 그 중 하나의 전자가 전달되어 생성되는 활성산소(activated oxygen)가 심장독성과 관련이 있는 것으로 알려져 있다. 이 때 퀴논 고리의 환원력(전자흡수능력)이 C-고리자체의 변환, 또는 인접 B-고리에 도입된 치환체의 영향으로 억제될 수 있다는 보고를 이론적 근거로 하여 안트라싸이클리논 골격을 전자흡수 능력을 가진 acridone 골격으로 치환한 화합물(1)과 안트라싸이클리논 골격을 유지하면서 aminosugar 부위를 pentopyranose계열을 도입 한 2 합성하였다. 화합물 1은 1,3-butadiene 과 1,4-benzoquinone 의 Diels-Alder adduct 3을 출발물질로 하여 7 단계의 반응과정으로 합성하였다.