New Generation of Polymeric Drugs: Copolymer from NIPAAM and Cyclodextrin Methacrylate Containing Supramolecular‐Attached Antitumor Derivative

Maciollek, Arkadius; Munteanu, Maricica; Ritter, Helmut

doi:10.1002/macp.200900436

Cited by 29 publications

(21 citation statements)

References 21 publications

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“…Complex 21 of adamantane-containing 5-fluorouracil analog 22 and cyclodextrin-containing copolymer 23 was prepared [17]. The complex was formed via noncovalent inclusion of adamantane moieties into cyclodextrin cavities.…”

Section: A-imentioning

confidence: 99%

Biological Activity of Adamantane-Containing Mono- and Polycyclic Pyrimidine Derivatives* (A Review)

Shokova

Ковалев

2016

Pharm Chem J

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Biological test results for a series of adamantane-containing pyrimidines, purines, and their derivatives that were synthesized and studied in 1999 -2001 are reviewed. Pyrimidine, purine, and similar scaffolds are exceedingly common key building blocks in the design of drugs with the broadest spectra of action comprising antibacterial, antiviral, antitumor, neurotropic, antifungal, immunotropic, and other types of drugs. An adamantane moiety in the molecules often has a substantial effect on the biological properties. Practically all studies included in the first part of the present review [1] explain their goals using just such factors. Therefore, almost every study consisted of two parts, i.e., chemical and biological.The previous studies focused on synthetic pyrimidine derivatives such as monocyclic pyrimidines (pyrimidinone, uracil, cytosine, uridines, etc.), condensed di-and polycyclic compounds (pyrazolopyrimidine, triazolopurine, xanthene, etc.), and adenosines with various substitution patterns and types of substituents. An adamantane moiety could be either bonded directly to the heterocycle or on its periphery. This part of the review focuses on biological tests of the synthesized compounds**. The subsections present research results according to individual type of biological activity. In addition, a subsection called Biological Screening was included. It includes results for instances where the activity of certain rather large groups (types) of compounds was studied for several rather than a single indication. This was most often related to characteristic antimicrobial, fungicidal, and antimalarial activity and the cytotoxicity of the drugs. In most instances, we considered it counterproductive to lump these results into piles in various sections. * Part 1 of the present review [1] contains information regarding the synthesis of adamantane-containing pyrimidine derivatives. ** The following terms [abbreviation and its explanation (if it exists) given in the corresponding publication] are used to present the biological test results:MIC, minimum inhibiting concentration [2, 3, 6]. MIC 50 , minimum inhibiting concentration suppressing development of virus-induced cytopathic activity by 50% [23,51]. MCC 50 , minimum cytotoxic concentration causing 50% inhibition of cell growth (VERO cells) [23,51]. CD 50 , cytotoxic dose causing 50% inhibition of cell growth [28]. CC 50 , cytotoxic concentration of a drug required to inhibit 50% of any subject in vitro [3,22]. EC 50 , 50% effective plasma concentration at which the effectiveness is 50% of the maximum for this drug in vivo [3,7,9,22]. ID, inhibiting dose; IC, inhibiting concentration, IC 50 , [5,6,9,10,41]; ID 80 , [3]; ID 95 , [28]. SI, selectivity index; SI = MCC 50 /MIC 50 [23, 51]; SI = CC 50 /EC 50 [3, 22]; SI = CD 50 /ID 50 [28]. pEC 50 , negative logarithm of EC 50 [46]. K i , equilibrium dissociation constant [42, 44, 45].

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Section: A-imentioning

confidence: 99%

Biological Activity of Adamantane-Containing Mono- and Polycyclic Pyrimidine Derivatives* (A Review)

Shokova

Ковалев

2016

Pharm Chem J

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“…Â ðàáîòå [17] áûë ïîëó÷åí êîìïëåêñ 21 àäàìàíòàíñîäåðaeàùåãî àíàëîãà 5-ôòîðóðàöèëà 22 ñ öèêëîäåêñòðèíñî-äåðaeàùèì ñîïîëèìåðîì 23. Îáðàçîâàíèå êîìïëåêñà ïðîèñõîäèò çà ñ÷åò íåêîâàëåíòíîãî âêëþ÷åíèÿ àäàìàíòàíî-âûõ ôðàãìåíòîâ ìîëåêóëû â öèêëîäåêñòðèíîâûå ïîëîñòè.…”

Section: ãðóïïàunclassified

Биологическая Активность Адамантансодержащих Моно- И Полициклических Пиримидиновых Производных (Обзор)

Shokova¹,

Ковалев²

2016

Хим.-фарм. ж.

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Ìîñêîâñêèé ãîñóäàðñòâåííûé óíèâåðñèòåò èì. Ì. Â. Ëîìîíîñîâà, Õèìè÷åñêèé ôàêóëüòåò; 119991, Ìîñêâà, Ëåíèíñêèå ãîðû, ôàêñ (495) Äàííûé îáçîð ïîñâÿù¸í èçëîaeåíèþ ðåçóëüòàòîâ áèîëîãè÷åñêèõ èñïûòàíèé ñèíòåçèðî-âàííûõ çà ïåðèîä 1999 -2011 ãã. àäàìàíòàíñîäåðaeàùèõ ïèðèìèäèíîâ, ïóðèíîâ è ðîäñò-âåííûõ èì ñîåäèíåíèé.Êëþ÷åâûå ñëîâà: àäàìàíòàíñîäåðaeàùèå ïèðèìèäèíû; ïóðèíû; ïðîèçâîäíûå ïèðèìè-äèíîâ.Ðîëü ïèðèìèäèíîâûõ, ïóðèíîâûõ è ïîäîáíûõ ñòðóêòóð êàê êëþ÷åâûõ ñòðîèòåëüíûõ áëîêîâ ïðè ñîçäàíèè ôàðìàöåâòè÷åñêèõ ïðåïàðàòîâ ñàìîãî øèðîêîãî ñïåêòðà äåéñòâèÿ ÷ðåçâû÷àéíî âåëèêà. Ýòî îòíîñèòñÿ ê àíòè-áàêòåðèàëüíûì è àíòèâèðóñíûì, ïðîòèâîîïóõîëåâûì è íåéðîòðîïíûì, ïðîòèâîãðèáêîâûì, èììóíîòðîïíûì è äðóãèì ëåêàðñòâåííûì ñðåäñòâàì. Íàëè÷èå àäàìàíòàíîâîãî ôðàãìåíòà â ìîëåêóëàõ çà÷àñòóþ îêàçûâàåò ñóùåñò-âåííîå âëèÿíèå íà áèîëîãè÷åñêèå ñâîéñòâà ñîåäèíåíèé. Èìåííî ýòèìè ôàêòîðàìè àâòîðû ïðàêòè÷åñêè âñåõ ðà-áîò, ñîáðàííûõ â I ÷àñòè íàñòîÿùåãî îáçîðà [1], îáúÿñíÿþò öåëü ñâîèõ èññëåäîâàíèé. Ïîýòîìó ïî÷òè êàaeäàÿ ðà-áîòà ñîñòîèò èç 2 ÷àñòåé -õèìè÷åñêîé è áèîëîãè÷åñêîé.Ïðåäñòàâëåííûå â ðàáîòàõ äàííûå ñâèäåòåëüñòâóþò î òîì, ÷òî âñå ñèíòåçèðîâàííûå ñîåäèíåíèÿ ÿâëÿþòñÿ ïðîèçâîäíûìè ïèðèìèäèíà. Ýòî -ìîíîöèêëè÷åñêèå ïèðèìèäèíû (ïèðèìèäèíîí, óðàöèë, öèòîçèí, óðèäèíû è ò.ä.), êîíäåíñèðîâàííûå äè-è ïîëèöèêëè÷åñêèå ñîåäèíåíèÿ (ïèðàçîëîïèðèìèäèí, òðèàçîëîïóðèí, êñàíòåí è ò.ä.), àäåíîçèíû ñ ñàìîé ðàçëè÷íîé ñòåïåíüþ çàìåùåíèÿ è ïðèðîäîé çàìåñòèòåëåé. Àäàìàíòàíîâûé ôðàãìåíò ìîaeåò áûòü ëèáî íåïîñðåäñòâåííî ñâÿçàí ñ ãåòåðîöèêëîì, ëèáî íàõîäèòñÿ íà ïåðèôåðèè ìîëåêóëû.Äàííûé ðàçäåë îáçîðà ïîñâÿùåí èçëîaeåíèþ ðåçóëüòàòîâ áèîëîãè÷åñêèõ èñïûòàíèé ñèíòåçèðîâàííûõ ñîåäè-íåíèé**. Ïîäðàçäåëû âêëþ÷àþò äàííûå èññëåäîâàíèé â ñîîòâåòñòâèè ñ îïðåäåëåííûì âèäîì áèîëîãè÷åñêîé àê-òèâíîñòè, êðîìå òîãî, ìû ââåëè ïîäðàçäåë ñ óñëîâíûì íàçâàíèåì "Áèîëîãè÷åñêèé ñêðèíèíã". Â íåãî âêëþ÷åíû ðåçóëüòàòû, ïîëó÷åííûå â òåõ ñëó÷àÿõ, êîãäà àêòèâíîñòü îïðåäåë¸ííûõ, äîñòàòî÷íî áîëüøèõ ãðóïï (òèïîâ) ñî-åäèíåíèé èçó÷àëàñü íå ïî îäíîìó, à ïî íåñêîëüêèì íàïðàâëåíèÿì, ÷àùå âñåãî ýòî ñâÿçàíî ñ õàðàêòåðèñòèêîé àí-òèìèêðîáíîé, ôóíãèöèäíîé, àíòèìàëÿðèéíîé àêòèâíîñòè è öèòîòîêñè÷íîñòè ïðåïàðàòîâ. Èçëàãàòü ýòè ðåçóëüòà-òû "êóñêàìè" â ðàçíûõ ðàçäåëàõ ìû â áîëüøèíñòâå ñëó÷àåâ íå ïîñ÷èòàëè öåëåñîîáðàçíûì.Õèìèêî-ôàðìàöåâòè÷åñêèé aeóðíàë. Òîì 50, ¹ 2, 2016 3 * Â ÷. I íàñòîÿùåãî îáçîðà [1] èçëîaeåíû ìàòåðèàëû, ñâÿçàííûå ñ ñèíòåçîì àäàìàíòàíñîäåðaeàùèõ ïèðèìèäèíîâûõ ïðîèçâîäíûõ. ** Ïðè èçëîaeåíèè äàííûõ áèîëîãè÷åñêèõ èññëåäîâàíèé àâòîðàìè ðàáîò áûëè èñïîëüçîâàíû ñëåäóþùèå ïîêàçàòåëè [ïðèâîäèòñÿ àááðåâèàòóðà è åå ðàñøèôðîâêà (åñëè îíà èìååòñÿ), äàííàÿ â ñîîòâåòñòâóþùåé ïóáëèêàöèè]: MIC -ìèíèìàëüíàÿ èíãèáèðóþùàÿ êîíöåíòðàöèÿ [2,3,6]. MIC 50 -ìèíèìàëüíàÿ èíãèáèðóþùàÿ êîíöåíòðàöèÿ ïðåïàðàòà, ïîäàâëÿþùàÿ ðàçâèòèå âèðóñèíäóöèðîâàííîãî öèòîïàòè÷åñêîãî äåéñòâèÿ íà 50 % [23,51]. MÑC 50 -ìèíèìàëüíàÿ öèòîòîêñè÷åñêàÿ êîíöåíòðàöèÿ, âûçûâàþùàÿ 50 % èíãèáèðîâàíèå ðîñòà êëåòîê (êëåòêè VERO) [23,51]. CD 50 -öèòîòîêñè÷åñêàÿ äîçà, âûçûâàþùàÿ 50 % èíãèáèðîâàíèå ðîñòà êëåòîê [28]. CÑ 50 -öèòîòîêñè÷åñêàÿ êîíöåíòðàöèÿ -êîíöåíòðàöè...

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“…An in vitro study showed that the DOX-loaded nanoparticles could release their payload in response to the endosomal-pH after being internalized by HeLa cells via a nonspecific endocytosis pathway. 59 2.3.2 Conjugation of CD derivatives to pre-existing polymers. 56 To obtain pure mono-vinyl substituted CD monomers, an improved method was reported further by the same group.…”

Section: Cd-pendant Polymersmentioning

confidence: 99%

Cyclodextrin-functionalized polymers as drug carriers for cancer therapy

Wei

2015

Biomater. Sci.

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Cyclodextrins (CDs) represent the most extensively investigated cyclic molecules due to their wide availability, facile functionalization, unique amphiphilicity and inclusion capacity. The marriage of CD chemistry with polymer science has generated novel biomaterials by integrating supermolecular host-guest chemistry and state-of-the-art polymer chemistry techniques. The current mini-review focuses on the recent progress in CD-functionalized polymers as drug carriers for cancer therapy. CD-functionalized polymers with different structures are summarized. Their application as drug carriers for cancer therapy is then highlighted. In the end, the future directions of this rapidly developing research field are discussed.

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New Generation of Polymeric Drugs: Copolymer from NIPAAM and Cyclodextrin Methacrylate Containing Supramolecular‐Attached Antitumor Derivative

Cited by 29 publications

References 21 publications

Biological Activity of Adamantane-Containing Mono- and Polycyclic Pyrimidine Derivatives* (A Review)

Biological Activity of Adamantane-Containing Mono- and Polycyclic Pyrimidine Derivatives* (A Review)

Биологическая Активность Адамантансодержащих Моно- И Полициклических Пиримидиновых Производных (Обзор)

Cyclodextrin-functionalized polymers as drug carriers for cancer therapy

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