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Analysis of docosanol using GC/MS:Method development,validation,and application to ex vivo human skin permeation studies

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Journal of Pharmaceutical Analysis 2022年第2期12卷 287-292页

作者： Vijay Kumar Shankar Mei Wang Srinivas Ajjarapu Praveen Kolimi Bharathi Avula Reena Murthy Ikhlas Khan Sathyanarayana Narasimha Murthy Department of Pharmaceutics and Drug Delivery University of MississippiOxfordMS38677USA natural products Utilization research Unit Agricultural Research ServiceU.S.Department of AgricultureOxfordMS38677USA National Center for Natural Products Research Research Institute of Pharmaceutical SciencesSchool of PharmacyUniversity of MississippiOxfordMS38677USA Topical products Testing LLC OxfordMS38677USA

Docosanol is the only US Food and Drug Administration(FDA)approved over-the-counter topical product for treating recurrent oral-facial herpes simplex labialis.Validated analytical methods for docosanol are required to demonstrate the bioequivalence of docosanol topical products.A gas chromatography/selected ion monitoring mode mass spectrometry(GC/SIM-MS)method was developed and validated for docosanol determination in biological samples.Docosanol and isopropyl palmitate(internal standard)were separated on a high-polarity GC capillary column with(88%cyanopropy)aryl-polysiloxane employed as the stationary phase.The ions of m/z 83 and 256 were selected to monitor docosanol and isopropyl palmitate,respectively;the total run time was 20 min.The GC/SIM-MS method was validated in accordance with US FDA guidelines,and the results met the US FDA acceptance criteria.The docosanol calibration standards were linear in the 100-10000 ng/mL concentration range(R^(2)>0.994).The recoveries for docosanol from the receptor fluid and skin homogenates were>93.2%and>95.8%,respectively.The validated method was successfully applied to analyze ex vivo human cadaver skin permeation samples.On applying Abreva®cream tube and Abreva®cream pump,the amount of docosanol that penetrated human cadaver skin at 48 h was 21.5±7.01 and 24.0±6.95 ng/mg,respectively.Accordingly,we concluded that the validated GC/SIM-MS was sensitive,specific,and suitable for quantifying docosanol as a quality control tool.This method can be used for routine analysis as a costeffective alternative to other techniques.

关键词： Docosanol Fatty alcohols Gas chromatography-mass spectrometry Topical formulation Skin permeation

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Application of mesenchymal stem cell therapy for the treatment of osteoarthritis of the knee: A concise review

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World Journal of Stem Cells 2019年第4期11卷 222-235页

作者： Ai-Tong Wang Ying Feng Hong-Hong Jia Meng Zhao Hao Yu Cell products of nationalEngineering research center National Stem Cell Engineering Research Center

Osteoarthritis(OA) refers to a chronic joint disease characterized by degenerative changes of articular cartilage and secondary bone hyperplasia. Since articular cartilage has a special structure, namely the absence of blood vessels as well as the low conversion rate of chondrocytes in the cartilage matrix, the treatment faces numerous clinical challenges. Traditional OA treatment(e.g., arthroscopic debridement, microfracture, autologous or allogeneic cartilage transplantation,chondrocyte transplantation) is primarily symptomatic treatment and pain management, which cannot contribute to regenerating degenerated cartilage or reducing joint inflammation. Also, the generated mixed fibrous cartilage tissue is not the same as natural hyaline cartilage. Mesenchymal stem cells(MSCs) have turned into the most extensively explored new therapeutic drugs in cell-based OA treatment as a result of their ability to differentiate into chondrocytes and their immunomodulatory properties. In this study, the preliminary results of preclinical(OA animal model)/clinical trials regarding the effects of MSCs on cartilage repair of knee joints are briefly summarized, which lay a solid application basis for more and deeper clinical studies on cell-based OA treatment.

关键词： Osteoarthritis Mesenchymal stem cells Stem cell therapy Clinical trials

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Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes

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Chinese Chemical Letters 2024年第4期35卷 346-351页

作者： Lei Shen Yang Zhang Linlin Zhang Chuanwang Liu Zhixian Ma Kangjiang Liang Chengfeng Xia Key Laboratory of Medicinal Chemistry for natural Resource Ministry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of PharmacyYunnan UniversityKunming 650500China

Spectroscopic investigations discovered that the in-situ generated phenylhydrazone anion was significantly bathochromically shifted to visible light region for photoactivation under irradiation. The photoexcited phenylhydrazone anion was potential to reduce aryl iodides via single electron transfer process for the subsequent radical chain reaction. A redox-neutral photochemical carbonylation of aryl iodides was developed on basis of the special spectroscopic features of phenylhydrazone anion. This protocol provided a convenient and efficient synthetic tool for accessing carbonylation products under redox neutral conditions without the need of transition-metals.

关键词： Organic anion Hydrazone Carbonylation Visible light Single electron transfer

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Ex vivo antioxidant effects of D-004, a lipid extract from Roystonea regia fruits, on rat prostate tissue

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Asian Journal of Andrology 2008年第4期10卷 659-666页

作者： Yohani Perez Vivian Molina Rosa Mas Roberto Menendez Rosa M. Gonzailez Ambar Oyarzabal Sonia Jimenez Laboratory of Biochemistry Center of Natural Products National Center for Scientific Research Havana City 6990 Cuba

Aim： To investigate whether oral treatment with D-004, a lipid extract of the Cuban royal palm fruit, produces antioxidant effects in the prostate tissue of normal and testosterone （T）-treated rats. Methods： In our first experiment, normal rats were distributed into five groups： one group treated with the vehicle and four groups treated with D-004 （100, 200, 400 or 800 mg/kg）. In our second experiment, rats were randomized into five groups： a negative control group and four T-injected groups. The latter were comprised of a positive control group treated with the vehicle, and three groups treated with D-004 （200, 400 or 800 mg/kg）. Results： In normal rats, D-004 （100-800 mg/kg） inhibited significantly and dose-dependently iron-initiated malondialdehyde （MDA） accumulation in prostate homogenates （35.7%-80.0%） vs. the controls. D-004 （200-800 mg/kg） significantly reduced baseline MDA and carbonyl groups in prostate homogenates of normal rats to approximately 80% and 50%, respectively, and totally （100%） in T-treated rats. Conclusion： Oral treatment with D-004 reduced MDA and carbonyl groups dose-dependently and markedly in normal and T-injected rats. These findings show that D-004 given at doses effective to prevent prostate hyperplasia also produces antioxidant effects in the prostate tissue.

关键词： D-004 Roystonea regia Cuban royal palm prostate hyperplasia lipid peroxidation antioxidant

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Allantoin Alleviates Seed Germination Thermoinhibition in Arabidopsis

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Phyton-International Journal of Experimental Botany 2022年第9期91卷 1893-1904页

作者： Songbei Ying Sasa Jing Leheng Cheng Haiqing Sun Yuan Tian Lulu Zhi Ping Li Shanghai Key Laboratory of Bio-Energy Crops Research Center for Natural ProductsPlant Science CenterSchool of Life SciencesShanghai UniversityShanghai200444China

Allantoin as the metabolite of purine catabolism can store and remobilize nitrogen for plant growth and development.However,emerging evidence suggests it also contributes to plant tolerance to stress response through altering abscisic acid(ABA)and reducing reactive oxygen species(ROS)level.1-CYS PEROXIREDOXIN(PER1)is a seed-specific antioxidant that enhances seed longevity through scavenging ROS over-accumulation.High temperature(HT)suppresses seed germination and induces seed secondary dormancy,called as seed germination thermoinhibition.However,the mechanism that allantoin and PER1 regulate seed germination thermoinhibition remains unknown.In this study,we reported that allantoin treatment enhances seed germination under HT stress.Consistently,the aln mutants displayed higher seed germination,as well as more accumulation of endogenous allantoin,than that of wild-type control.Further biochemical and genetic analyses showed that allantoin reduces ABA content under HT,and allantoin targets PER1 to efficiently scavenge HT-induced ROS accumulation,meanwhile,the function of allantoin requires PER1 during seed gemination thermotolerance.Collectively,our finding proposes a novel function of allantoin in enhancing seed germination tolerance to HT,and uncovers the underlying mechanism by which allantoin regulates seed germination through altering ABA metabolism and PER1-mediated ROS level under HT stress.

关键词： Seed germination high temperature allantoin PRE1

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Putrescine Enhances Seed Germination Tolerance to Heat Stress in Arabidopsis thaliana

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Phyton-International Journal of Experimental Botany 2022年第9期91卷 1879-1891页

作者： Shiyan Lu Yulan Hu Yilin Chen Yaru Yang Yue Jin Ping Li Xiangyang Hu Shanghai Key Laboratory of Bio-Energy Crops Research Center for Natural ProductsPlant Science CenterSchool of Life SciencesShanghai UniversityShanghai200444China

Putrescine(Put)as the compound of plant polyamines is catalyzed by arginine decarboxylase(ADC),which is encoded by two members,ADC1 and ADC2 in Arabidopsis,and ADC2 is mainly responsible for Put biosynthesis.Accumulated evidence demonstrates the important function of Put in plant growth and development,but its role in regulating seed germination under high temperature(HT)has not been reported yet.SOMNUS(SOM)is the negative regulator for seed germination thermoinhibition by altering downstream gibberellin(GA)and abscisic acid(ABA)metabolism.In this study,we found exogenous application of Put obviously alleviated the inhibition effect of HT on seed germination.Whereas pharmacological inhibition of endogenous Put level reduced seed germination under HT.Consistently,HT induced the rapid accumulation of Put level,and the adc2 mutant defi-ciency in Put biosynthesis also showed more sensitivity to HT stress.Furthermore,we found that the Put signal suppressed the expression of SOM and changed the transcriptional patterns of genes associated with GA/ABA metabolism.Genetic analysis also revealed SOM was epistatic to ADC2 to alter GA/ABA metabolism.Collectively,our finding reveals the novel function of Put in controlling seed germination under HT through SOM,and provides the possibility to develop Put as the innovational regulator for uniform seed germination under HT stress.

关键词： Putrescine seed germination heat stress SOM ADC2

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Traditional Chinese Medicines Against COVID‑19:A Global Overview

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World Journal of Traditional Chinese Medicine 2022年第3期8卷 279-313页

作者： Chang‑Liang Yao Wen‑Long Wei Jian‑Qing Zhang Qi‑Rui Bi Jia‑Yuan Li Ikhlas Khan Rudolf Bauer De‑An Guo Shanghai research center for Modernization of Traditional Chinese Medicine National Engineering Laboratory Research Center for TCM Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of SciencesShanghaiChina National Center for Natural Products Research School of PharmacyUniversity of MississippiMSUSA Department of Pharmacognosy Institute of Pharmaceutical SciencesUniversity of GrazGrazAustria

Coronavirus disease 2019(COVID‑19),caused by the severe acute respiratory syndrome coronavirus 2,continues to be a global concern.Traditional Chinese medicines(TCMs)are an important element of the fight against COVID‑19 in China.The combined application of TCMs and conventional medicines in the treatment of COVID‑19 has achieved beneficial results,including the resolution of symptoms,prevention of disease progression,and reduced mortality.In this review,we summarize and discuss the current applications of TCMs with respect to COVID‑19,as well as update the preclinical and clinical research,including chemical analysis,molecular mechanisms,quality control,drug development,and studies of clinical efficacy.The expectation is that a better understanding of the roles of TCMs against COVID‑19 will improve the response to COVID‑19,both in China and globally.

关键词： Coronavirus disease 2019 clinical efficacy molecular mechanism traditional Chinese medicine

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Regulatory perspectives of combination products

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Bioactive Materials 2022年第4期7卷 492-503页

作者： Jiaxin Tian Xu Song Yongqing Wang Maobo Cheng Shuang Lu Wei Xu Guobiao Gao Lei Sun Zhonglan Tang Minghui Wang Xingdong Zhang center for Medical Device Evaluation National Medical Products AdministrationBeijingChina NMPA Key Laboratory for Quality research and Control of Tissue Regenerative Biomaterial&Institute of Regulatory Science for Medical Devices&NMPA research Base of Regulatory Science for Medical Devices Sichuan UniversityChengduChina national Engineering research center for Biomaterials&College of Biomedical Engineering Sichuan UniversityChengduChina center for Drug Evaluation National Medical Products AdministrationBeijingChina

Combination products with a wide range of clinical applications represent a unique class of medical products that are composed of more than a singular medical device or drug/biological product.The product research and development,clinical translation as well as regulatory evaluation of combination products are complex and challenging.This review firstly introduced the origin,definition and designation of combination products.Key areas of systematic regulatory review on the safety and efficacy of device-led/supervised combination products were then presented.Preclinical and clinical evaluation of combination products was discussed.Lastly,the research prospect of regulatory science for combination products was described.New tools of computational modeling and simulation,novel technologies such as artificial intelligence,needs of developing new standards,evidence-based research methods,new approaches including the designation of innovative or breakthrough medical products have been developed and could be used to assess the safety,efficacy,quality and performance of combination products.Taken together,the fast development of combination products with great potentials in healthcare provides new opportunities for the advancement of regulatory review as well as regulatory science.

关键词： Combination products Definition Designation Safety and efficacy Regulatory science

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新型2-(取代苄硫基)-5-(4,6-二甲基嘧啶-2-硫甲基)-1,3,4-噁二唑化合物的合成及生物活性

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有机化学 2018年第11期38卷 3112-3117页

作者：汪洲洋徐涵靖赵建平刘幸海翁建全浙江工业大学化学工程学院杭州310032 National Center for Natural Products Research University of Mississippioxfordms38677

为寻找新型杂环活性化合物,通过活性亚结构拼接方法,以硫脲和乙酰丙酮为起始原料合成4,6-二甲基嘧啶-2-硫醇,随后经醚化、肼化、环化反应,最后与取代苄氯在微波辐射中合成得到13个新型2-(取代苄硫基)-5-(4,6-二甲基嘧啶-2-硫甲基)-1,3,4... 详细信息

为寻找新型杂环活性化合物,通过活性亚结构拼接方法,以硫脲和乙酰丙酮为起始原料合成4,6-二甲基嘧啶-2-硫醇,随后经醚化、肼化、环化反应,最后与取代苄氯在微波辐射中合成得到13个新型2-(取代苄硫基)-5-(4,6-二甲基嘧啶-2-硫甲基)-1,3,4-噁二唑化合物.生物活性测试结果表明,在50μg/m L浓度下,部分化合物对尖孢炭疽病菌、枸杞炭疽病菌、草莓炭疽病菌具有较好的杀菌活性,其中取代基为3-氟时对尖孢炭疽病菌的抑制率达到80.22%;若干化合物还表现出良好的抗杜氏利什曼原虫活性,其中取代基为3-氯, 4-溴, 3-氟和4-叔丁基时, IC_(50)值均低于25μg/mL,优于对照药剂巴龙霉素.

关键词：嘧啶环 1 3 4-噁二唑硫醚合成杀菌活性抗杜氏利什曼原虫活性

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新型含嘧啶环结构的1,3,4-噻二唑硫醚类化合物的合成及生物活性

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有机化学 2017年第4期37卷 1009-1015页

作者：李倩梅庞凯胜赵建平刘幸海翁建全浙江工业大学化学工程学院杭州310032 National Center for Natural Products Research University of Mississippioxford38677

为寻找新型杂环活性化合物,通过活性亚结构拼接方法,以硫脲和乙酰丙酮为起始原料合成4,6-二甲基嘧啶-2-硫醇,随后经醚化、肼化、环化和苄基化反应,采用微波促进方法合成了15个新型含嘧啶环结构的1,3,4-噻二唑硫醚类化合物.利用~1H NMR,^... 详细信息

为寻找新型杂环活性化合物,通过活性亚结构拼接方法,以硫脲和乙酰丙酮为起始原料合成4,6-二甲基嘧啶-2-硫醇,随后经醚化、肼化、环化和苄基化反应,采用微波促进方法合成了15个新型含嘧啶环结构的1,3,4-噻二唑硫醚类化合物.利用~1H NMR,^(13)C NMR,IR,ESI-MS及元素分析对其结构进行了表征确认.生物活性测试结果表明,在50μg/m L浓度下,部分目标化合物对尖孢炭疽菌、枸杞炭疽菌和草莓炭疽菌具有较好的杀菌活性,其中2-(3-氟苄硫基)-5-(4,6-二甲基嘧啶-2-甲硫基)-1,3,4-噻二唑(7i)对尖孢炭疽菌和草莓炭疽菌的抑制率分别为79.84%和73.46%;若干化合物还表现出良好的抗杜氏利什曼原虫活性,其中2-(2-氟苄硫基)-5-(4,6-二甲基嘧啶-2-甲硫基)-1,3,4-噻二唑(7h)和2-(4-氟苄硫基)-5-(4,6-二甲基嘧啶-2-甲硫基)-1,3,4-噻二唑(7j)的IC50分别为21.3和23.6μg/m L.

关键词：嘧啶环 1,3,4-噻二唑硫醚微波合成杀菌活性抗杜氏利什曼原虫活性

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