Synthesis of N 11-anchoring biotinylated artemisinin derivatives and their preliminary biological assessment

Pan, QiYu; Wang, ShaoZhong; Lu, Jin‐Jian; Meng, Linghua; Yao, Zhu‐Jun

doi:10.1007/s11426-010-0009-z

Cited by 4 publications

(5 citation statements)

References 18 publications

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“…The SIN fluorescent label was synthesized using the method reported in the literature (Pan et al, 2010). SIN and fluorescein isothiocyanate (FITC) served as raw materials, and a FITC fluorescent group was placed in the SIN C-1 position.…”

Section: Uhplc-ms/ms Analysismentioning

confidence: 99%

Polyvinylpyrrolidone microneedles for localized delivery of sinomenine hydrochloride: preparation, release behavior of in vitro & in vivo, and penetration mechanism

et al. 2020

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Sinomenine (SIN) is an anti-inflammatory alkaloid derived from Sinomenium acutum, and the products sinomenine hydrochloride (SH) tablets and injections have been marketed in China to treat rheumatoid arthritis (RA). Oral administration of SH has shortcomings of gastrointestinal irritation and low bioavailability. The injection may require professional training and higher cost. It is of interest to develop an alternative form that is easier to administer and avoids the first-pass metabolism. In this study, SHloaded dissolving microneedles (SH-MN) were fabricated using polyvinyl pyrrolidone and chondroitin sulfate with a casting method. In percutaneous permeation studies of In vitro, the cumulative permeation and permeation rate of SH-MN were 5.31 and 5.06 times higher than that of SH-gel (SH-G). In percutaneous pharmacokinetic studies, the values of the area under the curve after administration of SH-MN in the skin and blood were 1.43-and 1.63-fold higher than that of SH-G, respectively. In percutaneous absorption studies, SH-MN could absorb into tissue fluid; and dissolve after skin penetration. The drug was released along the channel and spread to surrounding skin tissue. After 4 h, the needle tip was almost completely dissolved, and the drug could penetrate to a depth of 200 lm under the skin. These results demonstrate that the SH-MN is an effective, safe, and simple strategy for transdermal SH delivery.

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Section: Uhplc-ms/ms Analysismentioning

confidence: 99%

Polyvinylpyrrolidone microneedles for localized delivery of sinomenine hydrochloride: preparation, release behavior of in vitro & in vivo, and penetration mechanism

et al. 2020

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“…The needed aminated probes based on 11-aza-artemisinin derivatives for our target identification are shown in Figure 1b. Compound AAD1 (6, Figure 1a and Scheme 1) was firstly prepared according to our previous synthesis procedure, [28] and AAD2 (9, Figure 1a and Scheme 2) was further synthesized by attachment with a hydrophilic chain linker, a solubilizing PEG substructure. Anticancer activities of AAD1 and AAD2 were then evaluated by in vitro assay against multiple human cancer cell lines (Supplementary Figure 1a online), and showed similar bioactivity with half-maximal inhibitory concentration (IC 50 ) values in the micromolar range.…”

Section: Resultsmentioning

confidence: 99%

“…Natural product compounds AAD1 6 was afforded in high yield by the reaction of natural artemisinin 1 with hydrazine hydrate according to previous methodology. [25,28] Then, acid 7 [45] was reacted with AAD1 6 in the presence of EDCI and HOBt, providing compound 8. Treatment of 8 with TFA afforded the desired AAD2 9.…”

Section: Methodsmentioning

confidence: 99%

11‐Aza‐artemisinin Derivatives Exhibit Anticancer Activities by Targeting the Fatty Acid Binding Protein 6 (FABP6)

et al. 2018

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Artemisinin (Qinghaosu), a sesquiterpene lactone isolated from the Chinese medicinal herb Artemisia annua, is famous as the first‐line antimalarial drug, and reported to also possess anticancer properties. Though many studies have proceeded focusing on artemisinin and bioactive derivatives in clinic or laboratory, their cellular targets and mechanism of actions have still remained obscure. Here, two new 11‐aza‐artemisinin derivatives AAD1 and AAD2, which displayed cytotoxity against multiple cancer cell lines, were synthesized and applied as the probes for target identification and anticancer mechanism research. Using T7 phage display screen method, fatty acid binding protein 6 (FABP6) was identified and verified as one of the potential targets. Further studies showed FABP6 is a direct binding protein of AAD1 and AAD2, and mediated the corresponding anticancer activities of these artemisinin derivatives.

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“…13 Indeed, the biotin-avidin system has often been used to identify the target proteins of a substrate. Building on the work of Singh and co-workers, 12 their group synthesized the azaartemisines 6j and 15 (Structure block 3).…”

Section: N-biotinylated Azaartemisinin Derivativesmentioning

confidence: 99%

Synthesis, reactions and biological activity of 11-azaartemisinin and derivatives

Alen¹,

Truong²,

Nguyễn³

et al. 2011

Arkivoc

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In this review, we will give an overview of the synthesis and reactions of 11-azaartemisinins and their derivatives, from the first report in 1995 till now. The desoxo as well as the 9-desmethyl analogues are included. The biological activity of the azaartemisinins is also briefly discussed, with an emphasis on their potency as antimalarials. Computational studies on this type of compounds are beyond the scope of this review and will not be discussed, nor referenced.

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Synthesis of N 11-anchoring biotinylated artemisinin derivatives and their preliminary biological assessment

Cited by 4 publications

References 18 publications

Polyvinylpyrrolidone microneedles for localized delivery of sinomenine hydrochloride: preparation, release behavior of in vitro & in vivo, and penetration mechanism

Polyvinylpyrrolidone microneedles for localized delivery of sinomenine hydrochloride: preparation, release behavior of in vitro & in vivo, and penetration mechanism

11‐Aza‐artemisinin Derivatives Exhibit Anticancer Activities by Targeting the Fatty Acid Binding Protein 6 (FABP6)

Synthesis, reactions and biological activity of 11-azaartemisinin and derivatives

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