The ability of isatin derivatives (in particular, aminoacetylhydrazones) to intercalate into DNA and to induce interferon secretion is demonstrated for the first time. The toxicity of isatin derivatives is much lower and its interferon inducing activity is somewhat lower as compared to the analogous benzoisatin derivatives. The DNA affinity of benzoisatin derivatives is two orders of magnitude greater than that of isatin derivatives.
В работе впервые установлена способность производных изатина, в частности их аминоацетилгидразонов, к интеркаляции в ДНК и индукции интерферона. Производные изатина оказались значительно менее токсичными и несколько менее активными интерфероногенами, чем аналогичные им производные бензоизатина. Последние обладают на два порядка большим аффинитетом к ДНК, чем производные изатина.
The dependence of the affinity of compounds to DNA on the structure of their fragments intercalating into the double helix was studied in a series of aminoacetylhydrazones of 9-formylacridine and 9-formylanthracene. The synthesized compounds were characterized by the intercalating properties and the ability to inhibit the polymerase chain reaction (PCR). The affinity to DNA was found to be higher for acridine derivatives (log Ka = 7.37 – 8.04) than for anthracene derivatives (log Ka = 5.37 – 6.12). At the same time, both acridines and anthracenes showed insignificant ability to inhibit PCR. Thus, no correlation between the affinity to DNA and the ability to inhibit DNA replication was observed for the compounds studied.
To reveal the influence of intercalating fragment on the affinity to DNA aminoacetylhydrazones of 9-formylacridine and 9-formylanthracene are synthesized and their properties as intercalators and ability to inhibit the polymerase chain reaction are studied. It is shown, that the acridine derivatives (lg K а = 7.37 - 8.04) are more affine to DNA than the anthracene derivatives (lg K а = 5.37 - 6.12). Both acridines and anthracenes are characterized by insignificant ability to inhibit PCR. Correlation between affinity to DNA and ability to inhibit replication is absent.
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ChemInformVolume 34, Issue 35 Natural Products Synthesis and DNA-Binding Properties of Acridinylhydrazides (VI) of N,N-Dialkylglycines. E. A. Lyakhova, E. A. Lyakhova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorS. A. Lyakhov, S. A. Lyakhov Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorL. A. Litvinova, L. A. Litvinova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorZ. M. Topilova, Z. M. Topilova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorI. V. Vel'cheva, I. V. Vel'cheva Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorA. I. Gren', A. I. Gren' Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorM. N. Lebedyuk, M. N. Lebedyuk Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorV. P. Fedchuk, V. P. Fedchuk Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorG. A. Khorokhorina, G. A. Khorokhorina Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this author E. A. Lyakhova, E. A. Lyakhova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorS. A. Lyakhov, S. A. Lyakhov Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorL. A. Litvinova, L. A. Litvinova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorZ. M. Topilova, Z. M. Topilova Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorI. V. Vel'cheva, I. V. Vel'cheva Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorA. I. Gren', A. I. Gren' Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorM. N. Lebedyuk, M. N. Lebedyuk Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorV. P. Fedchuk, V. P. Fedchuk Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this authorG. A. Khorokhorina, G. A. Khorokhorina Fiz.-khim. inst. im. Bogatskogo Nats. Akad. nauk Ukr., Odessa 270080, UkraineSearch for more papers by this author First published: 04 August 2003 https://doi.org/10.1002/chin.200335157Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume34, Issue35September 2, 2003 RelatedInformation
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Antiviral and interferon inducing activity of the amixine and its some derivatives, as well as their influence on the proteolytic enzymes activity, monooxygenase activity of the microsomal fraction, level of the lipids peroxidation were studied. Lack of correlation between antiviral and interferon inducing activity in the investigated series of compounds was found. Vice versa, the good correlation between interferon inducing activity and the elastase-like activities inhibition ability of the compounds was observed. It allows to state the assumption, that only one ability of compounds to induce of an interferon doesn't suffice for obtaining of high titres of interferon, and while their rather high antiproteolitic activity is necessary. It's shown, that except for one compound the influence of amixine and its derivatives on the red-ox enzymes activity well correlates with their ability to the interferon-inducing. All presented above allows to attribute amixine and its derivatives to polymodal antiviral agents.
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.