548-39-0Relevant academic research and scientific papers
Synthesis of perinaphthenones through rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with alkynes
Fukuyama, Takahide,Sugimori, Taiki,Maetani, Shinji,Ryu, Ilhyong
, p. 7583 - 7587 (2018)
An efficient approach to the synthesis of perinaphthenones via the rhodium-catalyzed dehydrative annulation of 1-naphthoic acids with internal alkynes was developed. Norbornadiene can act as an acetylene equivalent to give unsubstituted perinaphthenones at the 2- and 3-positions via dehydrative annulation followed by a retro Diels-Alder reaction.
4-Hydroxyl-oxoisoaporphine, one small molecule as theranostic agent for simultaneous fluorescence imaging and photodynamic therapy as type II photosensitizer
Xu, Qi,Ji, Yunfan,Chen, Meijun,Shao, Xusheng
, p. 501 - 512 (2021)
Oxoisoaporphine (OA) is a plant phototoxin isolated from Menispermaceae, however, its weak fluorescence and low water solubility impede it for theranostics. We developed here 4-hydroxyl-oxoisoaporphine (OHOA), which has good singlet oxygen-generating ability (0.06), strong fluorescence (0.72) and improved water solubility. OHOA displays excellent fluorescence for cell imaging and exhibits light-induced cytotoxicity against cancer cell. In vitro model of human cervical carcinoma (HeLa) cell proved that singlet oxygen generated by OHOA triggered photosensitized oxidation reactions and exert toxic effect on tumor cells. The MTT assay using HeLa cells verified the low cytotoxicity of OHOA in the dark and high phototoxicity. Confocal experiment indicates that OHOA mainly distributes in mitochondria and western blotting demonstrated that OHOA induces cell apoptosis via the mitochondrial pathway in the presence of light. Our molecule provides an alternative choice as a theranostic agent against cancer cells which usually are in conflict with each other for most traditional theranostic agents. Graphic abstract: [Figure not available: see fulltext.]
Synthesis and insecticidal evaluation of phytoalexin phenalenones derivatives
Zhang, Ya-Nan,Feng, Yi-An,Li, Zhong,Shao, Xu-Sheng
, p. 1228 - 1231 (2017)
Phenalenone is a kind of defensive compound biosynthesized inside plants in response to the outside attack such as fungus and nematodes. A set of derivatives encompassing structural modifications on the privileged phenalenone scaffold were synthesized through introduction of phenyl and hydroxyl substitutes at 9-positon and 2-position and assessed their insecticidal activities against armyworm (Mythimna separata Walker) and cowpea aphids (Aphis craccivora). No obvious insecticidal activities of the synthesized compounds were observed against armyworm. Some of the 9-phenyl and 2-hydroxy substituted phenalenone analogues showed potential activities against cowpea aphids with 33%–41% mortality at 500?mg/L.
Measuring human carboxylesterase 2 activity in pancreatic cancer patient-derived xenografts using a ratiometric fluorescent chemosensor
Kailass, Karishma,Sadovski, Oleg,Capello, Michela,Kang, Ya'an,Fleming, Jason B.,Hanash, Samir M.,Beharry, Andrew A.
, p. 8428 - 8437 (2019)
Irinotecan-based therapy is a common treatment for pancreatic cancer. To elicit its anticancer activity, the drug requires first the hydrolysis action of the enzyme human carboxylesterase 2 (hCES2). It has been established that pancreatic cancer patients have various levels of hCES2, whereby patients having low levels respond poorer to Irinotecan than patients with higher levels, suggesting that hCES2 can be used to predict response. However, current methods that measure hCES2 activity are inaccurate, complex or lengthy, thus being incompatible for use in a clinical setting. Here, we developed a small molecule ratiometric fluorescent chemosensor that accurately measures hCES2 activity in a single-step within complex mixtures. Our chemosensor is highly selective for hCES2 over hCES1, cell permeable and can measure hCES2 activity in pancreatic cancer patient-derived xenografts. Given the simplicity, accuracy and tissue compatibility of our assay, we anticipate our chemosensor can be used to predict patient response to Irinotecan-based therapy.
Light-induced activities of novel naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphine derivatives towards mosquito larvae
Feng, Hao,Shao, Xusheng,Xu, Qi
supporting information, (2021/07/14)
Infected mosquitoes are significant vectors of dengue, yellow fever, chikungunya, zika and other pathogens. In the view of increasing resistance in mosquito larvae control, photoactivated insecticides is a promising approach by utilizing highly toxic singlet oxygen produced by photosensitizer through irradiation. However, the choice of photosensitizer for mosquito control is limited. Here, we report a novel series of naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphines derivatives as excellent type II photosensitizers. Meanwhile, the light-dependent activities against permethrin-susceptible and permethrin-resistant strain of Aedes aegypti mosquito larvae of these compounds were evaluated. Among them, compound 7b was proved to be potential photodynamic insecticide due to its excellent phototoxicity, the LC50 value was 0.19 μg mL?1 under visible light irradiation. The irradiation-generated enhancement in the activity was more than 520-fold. This compound could be the potential candidate in the search for new photoactivated insecticide leads. Importantly, 7b has good fluorescence quantum yield (?F = 0.70), it can be used as a fluorescence indicator in mosquito larvae to observe uptake and morphology change.
A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy
Kaye, Esther G.,Kailass, Karishma,Sadovski, Oleg,Beharry, Andrew A.
supporting information, p. 1295 - 1301 (2021/08/01)
Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.
Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer
Wang, Ming-Zhong,Ku, Chuen-Fai,Si, Tong-Xu,Tsang, Siu-Wai,Lv, Xiao-Meng,Li, Xiao-Wan,Li, Zheng-Ming,Zhang, Hong-Jie,Chan, Albert S. C.
, p. 98 - 105 (2018/02/07)
Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel-Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.
Synthesis of Positional Isomeric Phenylphenalenones
Ospina, Felipe,Ramirez, Adrian,Cano, Marisol,Hidalgo, William,Schneider, Bernd,Otálvaro, Felipe
, p. 3873 - 3879 (2017/04/11)
A series of isomeric phenylphenalenones in which the phenyl ring is located at all possible peripheral positions of the phenalenone nuclei was synthesized. The structural characteristics of the series, in which topological variation is permitted with minimal electronic disturbance, could, in principle, allow for easy pharmacophore recognition when the compounds are aligned in steroidomimetic conformations.
Improving photodynamic inactivation of bacteria in dentistry: Highly effective and fast killing of oral key pathogens with novel tooth-colored type-II photosensitizers
Sp?th, Andreas,Leibl, Christoph,Cieplik, Fabian,Lehner, Karin,Regensburger, Johannes,Hiller, Karl-Anton,B?umler, Wolfgang,Schmalz, Gottfried,Maisch, Tim
, p. 5157 - 5168 (2014/07/08)
Increasing antibiotic resistances in microorganisms create serious problems in public health. This demands alternative approaches for killing pathogens to supplement standard treatment methods. Photodynamic inactivation of bacteria (PIB) uses light activated photosensitizers (PS) to generate reactive oxygen species immediately upon illumination, inducing lethal phototoxicity. Positively charged phenalen-1-one derivatives are a new generation of PS for light-mediated killing of pathogens with outstanding singlet oxygen quantum yield ΦΔ of >97%. Upon irradiation with a standard photopolymerizer light (bluephase C8, 1260 ± 50 mW/cm2) the PS showed high activity against the oral key pathogens Enterococcus faecalis, Actinomyces naeslundii, Streptococcus mutans, and Aggregatibacter actinomycetemcomitans. At a concentration of 10 μM, a maximum efficacy of more than 6 log10 steps (≥99.9999%) of bacteria killing is reached in less than 1 min (light dose 50 J/cm2) after one single treatment. The pyridinium substituent as positively charged moiety is especially advantageous for antimicrobial action.
Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity
Smith III, Amos B.,Kim, Won-Suk
, p. 6787 - 6792 (2012/03/26)
In conjunction with the construction of a diversity-oriented synthesis library of 10-membered ring "natural product-like" macrolides, the design, synthesis, and validation of a unique class of bifunctional linchpins, uniting benzyne reactivity initiated by type II anion relay chemistry (ARC) has been achieved, permitting access to diverse [2+2], [3+2], and [4+2] cycloadducts.
