Isonicotinic acid (BioDeep_00000000762)

 

Secondary id: BioDeep_00000400243

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Pyridine-4-carboxylic Acid; Nicotinic Acid Imp. E (EP); Isonicotinic Acid; Isoniazid Impurity A; Nicotinic Acid Impurity E

化学式: C6H5NO2 (123.032027)
中文名称: 异烟酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.09%

分子结构信息

SMILES: C1=CN=CC=C1C(=O)O
InChI: InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)

描述信息

Isonicotinic acid is a pyridinemonocarboxylic acid in which the carboxy group is at position 4 of the pyridine ring. It has a role as a human metabolite and an algal metabolite. It is a conjugate acid of an isonicotinate.
Isonicotinic acid is a natural product found in Aloe africana, Chlamydomonas reinhardtii, and other organisms with data available.
Heterocyclic acids that are derivatives of 4-pyridinecarboxylic acid (isonicotinic acid).
Isonicotinic acid is a metabolite of isoniazid. Isonicotinic acid is an organic compound with a carboxyl group on a pyridine ring. It is an isomer of nicotinic acid. The carboxyl group for isonicotinic acid is on the 4-position instead of the 3-position for nicotinic acid (Wikipedia).
A pyridinemonocarboxylic acid in which the carboxy group is at position 4 of the pyridine ring.
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID I017
Isonicotinic acid is a metabolite of Isoniazid. Isoniazid is converted to Isonicotinic acid by hydrazinolysis, with the Isoniazid to Isonicotinic acid biotransformation also to be catalyzed by cytochrome P450 (CYP) enzymes, e.g., CYP2C[1].

同义名列表

54 个代谢物同义名

Pyridine-4-carboxylic Acid; Nicotinic Acid Imp. E (EP); Isonicotinic Acid; Isoniazid Impurity A; Nicotinic Acid Impurity E; Isonicotinic acid; Isoniazid, 4-pyridinecarboxylic acid, p-pyridinecarboxylic acid, 4-Picolinic acid; InChI=1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9; Pyridine-4-carboxylic Acid (Isonicotinic Acid); Isonicotinic acid, SAJ special grade, >=99.0\\%; Isonicotinic acid, purum, >=99.0\\% (T); ISONIAZID IMPURITY A [EP IMPURITY]; .gamma.-pyridinecarboxylic acid; Acide iso-nicotinique [French]; gamma-Pyridinecarboxylic acid; 1,4-Dihydroisonicotinic acid; Pyridinecarboxylic acid-(4); ISONICOTINIC ACID [WHO-DD]; 4-pyridine-carboxylic acid; Pyridine-4-carboxylic acid; gamma-Pyridinecarboxylate; 4-Pyridinecarboxylic acid; g-Pyridinecarboxylic acid; p-Pyridinecarboxylic acid; Γ-pyridinecarboxylic acid; Isonicotinic acid, 99\\%; .gamma.-Picolinic acid; .alpha.-Picolinic acid; ISONICOTINIC ACID [MI]; g-Pyridinecarboxylate; Γ-pyridinecarboxylate; p-Pyridinecarboxylate; Acide iso-nicotinique; 4-Pyridinecarboxylate; isonicotinic-d4 acid; gamma-Picolinic acid; Acids, Isonicotinic; Acid, Isonicotinic; Isonicotinic Acids; isonicotonic acid; Isonicotinic acid; 4-Carboxypyridine; isonicotinicacid; Γ-picolinic acid; gamma-Picolinate; g-Picolinic acid; 4-Picolinic acid; UNII-Y8SYN761TQ; BPBio1_001365; Isonicotinate; Oprea1_749724; Tox21_200502; g-Picolinate; Γ-picolinate; CAS-55-22-1; Y8SYN761TQ; AI3-19239; MN1; S3V



数据库引用编号

33 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

8 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Zainab Fakih, Mélodie B Plourde, Charlène Eugénie Tomi Nkouankou, Victor Fourcassié, Sylvie Bourassa, Arnaud Droit, Hugo Germain. Specific alterations in riboproteomes composition of isonicotinic acid treated arabidopsis seedlings. Plant molecular biology. 2023 Mar; 111(4-5):379-392. doi: 10.1007/s11103-022-01332-2. [PMID: 36790538]
  • Shengfu Wang, Chunyan Wang, Xiao Wang, Xiang Wang, Lina Huang, Jiajie Kuai, Wei Wei, Xiaorong Lu, Shangxue Yan. Antitumor efficacy of CHMFL-KIT-110 solid dispersion in mouse xenograft models of human gastrointestinal stromal tumors. Cancer chemotherapy and pharmacology. 2021 11; 88(5):795-804. doi: 10.1007/s00280-021-04332-z. [PMID: 34309733]
  • Xu-Xu Huang, Yong Wang, Ji-Shan Lin, Lu Chen, Yan-Jie Li, Qian Liu, Guan-Feng Wang, Fang Xu, Lijing Liu, Bing-Kai Hou. The novel pathogen-responsive glycosyltransferase UGT73C7 mediates the redirection of phenylpropanoid metabolism and promotes SNC1-dependent Arabidopsis immunity. The Plant journal : for cell and molecular biology. 2021 07; 107(1):149-165. doi: 10.1111/tpj.15280. [PMID: 33866633]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Keren Martínez-Aguilar, José Luis Hernández-Chávez, Raúl Alvarez-Venegas. Priming of seeds with INA and its transgenerational effect in common bean (Phaseolus vulgaris L.) plants. Plant science : an international journal of experimental plant biology. 2021 Apr; 305(?):110834. doi: 10.1016/j.plantsci.2021.110834. [PMID: 33691968]
  • Yiming Yin, Mengge Wang, Wenjie Gu, Lili Chen. Intestine-specific FXR agonists as potential therapeutic agents for colorectal cancer. Biochemical pharmacology. 2021 04; 186(?):114430. doi: 10.1016/j.bcp.2021.114430. [PMID: 33556338]
  • Galyna P Volynets, Michail A Tukalo, Volodymyr G Bdzhola, Nataliia M Derkach, Mykola I Gumeniuk, Sergiy S Tarnavskiy, Sergiy M Yarmoluk. Novel isoniazid derivative as promising antituberculosis agent. Future microbiology. 2020 07; 15(?):869-879. doi: 10.2217/fmb-2019-0085. [PMID: 32662670]
  • Keyur Patel, Stephen A Harrison, Magdy Elkhashab, James F Trotter, Robert Herring, Sergio E Rojter, Zeid Kayali, Vincent Wai-Sun Wong, Susan Greenbloom, Saumya Jayakumar, Mitchell L Shiffman, Bradley Freilich, Eric J Lawitz, Edward J Gane, Eliza Harting, Jun Xu, Andrew N Billin, Chuhan Chung, C Stephen Djedjos, G Mani Subramanian, Robert P Myers, Michael S Middleton, Mary Rinella, Mazen Noureddin. Cilofexor, a Nonsteroidal FXR Agonist, in Patients With Noncirrhotic NASH: A Phase 2 Randomized Controlled Trial. Hepatology (Baltimore, Md.). 2020 07; 72(1):58-71. doi: 10.1002/hep.31205. [PMID: 32115759]
  • Mingming Liu, Tatsunori Masatani, Paul Franck Adjou Moumouni, Seung-Hun Lee, Eloiza May Galon, Yang Gao, Huanping Guo, Jixu Li, Yongchang Li, Xuenan Xuan. Inhibitory effects of the phytohormone inhibitors fluridone and inabenfide against Babesia gibsoni in vitro. Veterinary parasitology. 2019 Jan; 265(?):19-23. doi: 10.1016/j.vetpar.2018.11.018. [PMID: 30638516]
  • Hongshi Jin, Sun-Mee Choi, Min-Jeong Kang, Se-Hun Yun, Dong-Jin Kwon, Yoo-Sun Noh, Bosl Noh. Salicylic acid-induced transcriptional reprogramming by the HAC-NPR1-TGA histone acetyltransferase complex in Arabidopsis. Nucleic acids research. 2018 12; 46(22):11712-11725. doi: 10.1093/nar/gky847. [PMID: 30239885]
  • Muhammad Binyameen, Masood Ejaz, Sarfraz Ali Shad, Muhammad Razaq, Rizwan Mustafa Shah, Fredrik Schlyter. Eugenol, a Plant Volatile, Synergizes the Effect of the Thrips Attractant, Ethyl Iso-Nicotinate. Environmental entomology. 2018 12; 47(6):1560-1564. doi: 10.1093/ee/nvy153. [PMID: 30346518]
  • Diego Durango, Jennifer Murillo, Fernando Echeverri, Gustavo Escobar, Winston Quiñones. Isoflavonoid composition and biological activity of extracts from soybean seedlings treated by different elicitors. Anais da Academia Brasileira de Ciencias. 2018 Aug; 90(2 suppl 1):1955-1971. doi: 10.1590/0001-3765201820170785. [PMID: 30066748]
  • D Cocking, J Cinatl, D A Boltz, X Peng, W Johnson, M Muzzio, O Syarkevych, G Kostyuk, A Goy, L Mueller, V I Margitich. Antiviral effect of a derivative of isonicotinic acid enisamium iodide (FAV00A) against influenza virus. Acta virologica. 2018 ; 62(2):191-195. doi: 10.4149/av_2018_211. [PMID: 29895160]
  • Rana Abu Farha, Yasser Bustanji, Yusuf Al-Hiari, Sanaa Bardaweel, Tariq Al-Qirim, Ghassan Abu Sheikha, Rabab Albashiti. Pharmacological Evaluation of Novel Isonicotinic Carboxamide Derivatives as Potential Anti-Hyperlipidemic and Antioxidant Agents. Archiv der Pharmazie. 2017 Oct; 350(10):. doi: 10.1002/ardp.201700024. [PMID: 28837755]
  • Felicitas Groß, Eva-Esther Rudolf, Björn Thiele, Jörg Durner, Jeremy Astier. Copper amine oxidase 8 regulates arginine-dependent nitric oxide production in Arabidopsis thaliana. Journal of experimental botany. 2017 04; 68(9):2149-2162. doi: 10.1093/jxb/erx105. [PMID: 28383668]
  • Stanislav A Pshenichnyuk, Alexei S Komolov. Why Can Unnatural Electron Acceptors Protect Photosynthesizing Organisms but Kill the Others?. The journal of physical chemistry. B. 2017 02; 121(4):749-757. doi: 10.1021/acs.jpcb.6b12007. [PMID: 28072544]
  • Sergio Molinari. Systemic acquired resistance activation in solanaceous crops as a management strategy against root-knot nematodes. Pest management science. 2016 May; 72(5):888-96. doi: 10.1002/ps.4063. [PMID: 26085141]
  • Ekaterina Lakontseva, Ruben Karapetian, Mikhail Krasavin. New Antimycobacterial Leads from Multicomponent Hydrazino-Ugi Reaction. Medicinal chemistry (Shariqah (United Arab Emirates)). 2016; 12(2):191-9. doi: 10.2174/157340641202160209111507. [PMID: 26427929]
  • Kok-Yong Seng, Kim-Hor Hee, Gaik-Hong Soon, Nicholas Chew, Saye H Khoo, Lawrence Soon-U Lee. Population pharmacokinetic analysis of isoniazid, acetylisoniazid, and isonicotinic acid in healthy volunteers. Antimicrobial agents and chemotherapy. 2015 Nov; 59(11):6791-9. doi: 10.1128/aac.01244-15. [PMID: 26282412]
  • Yan Zhang, Mark S Warren, Xuexiang Zhang, Sharon Diamond, Bill Williams, Naresh Punwani, Jane Huang, Yong Huang, Swamy Yeleswaram. Impact on creatinine renal clearance by the interplay of multiple renal transporters: a case study with INCB039110. Drug metabolism and disposition: the biological fate of chemicals. 2015 Apr; 43(4):485-9. doi: 10.1124/dmd.114.060673. [PMID: 25605813]
  • Martina Sutovska, Michaela Kocmalova, Marta Joskova, Marian Adamkov, Sona Franova. The effect of long-term administered CRAC channels blocker on the functions of respiratory epithelium in guinea pig allergic asthma model. General physiology and biophysics. 2015 Apr; 34(2):167-76. doi: 10.4149/gpb_2014031. [PMID: 25730896]
  • Jan Bureš, Hana Jansová, Ján Stariat, Tomáš Filipský, Přemysl Mladěnka, Tomáš Šimůnek, Radim Kučera, Jiří Klimeš, Qin Wang, Katherine J Franz, Petra Kovaříková. LC-UV/MS methods for the analysis of prochelator-boronyl salicylaldehyde isonicotinoyl hydrazone (BSIH) and its active chelator salicylaldehyde isonicotinoyl hydrazone (SIH). Journal of pharmaceutical and biomedical analysis. 2015 Feb; 105(?):55-63. doi: 10.1016/j.jpba.2014.11.044. [PMID: 25527982]
  • Lei Ding, Run Gao, Xiao-Qing Xiong, Xing-Ya Gao, Qi Chen, Yue-Hua Li, Yu-Ming Kang, Guo-Qing Zhu. GABA in Paraventricular Nucleus Regulates Adipose Afferent Reflex in Rats. PloS one. 2015; 10(8):e0136983. doi: 10.1371/journal.pone.0136983. [PMID: 26317425]
  • Łukasz Janus, Grzegorz Milczarek, Magdalena Arasimowicz-Jelonek, Dariusz Abramowski, Hanna Billert, Jolanta Floryszak-Wieczorek. Normoergic NO-dependent changes, triggered by a SAR inducer in potato, create more potent defense responses to Phytophthora infestans. Plant science : an international journal of experimental plant biology. 2013 Oct; 211(?):23-34. doi: 10.1016/j.plantsci.2013.06.007. [PMID: 23987808]
  • Magdalena Arasimowicz-Jelonek, Arkadiusz Kosmala, Łukasz Janus, Dariusz Abramowski, Jolanta Floryszak-Wieczorek. The proteome response of potato leaves to priming agents and S-nitrosoglutathione. Plant science : an international journal of experimental plant biology. 2013 Jan; 198(?):83-90. doi: 10.1016/j.plantsci.2012.10.004. [PMID: 23199689]
  • Jolanta Floryszak-Wieczorek, Magdalena Arasimowicz-Jelonek, Grzegorz Milczarek, Lukasz Janus, Sylwia Pawlak-Sprada, Dariusz Abramowski, Joanna Deckert, Hanna Billert. Nitric oxide-mediated stress imprint in potato as an effect of exposure to a priming agent. Molecular plant-microbe interactions : MPMI. 2012 Nov; 25(11):1469-77. doi: 10.1094/mpmi-02-12-0044-r. [PMID: 22835274]
  • Sarah D Brown, Katherine D Trotter, Oliver B Sutcliffe, Jane A Plumb, Bruce Waddell, Naomi E B Briggs, Nial J Wheate. Combining aspects of the platinum anticancer drugs picoplatin and BBR3464 to synthesize a new family of sterically hindered dinuclear complexes; their synthesis, binding kinetics and cytotoxicity. Dalton transactions (Cambridge, England : 2003). 2012 Oct; 41(37):11330-9. doi: 10.1039/c2dt31313h. [PMID: 22886151]
  • Shiraz A Markarian, Mikayel G Aznauryan. Study on the interaction between isoniazid and bovine serum albumin by fluorescence spectroscopy: the effect of dimethylsulfoxide. Molecular biology reports. 2012 Jul; 39(7):7559-67. doi: 10.1007/s11033-012-1590-3. [PMID: 22327779]
  • Veronika Biricová, Alice Lázničková, Milan Lázníček, Miloslav Polášek, Petr Hermann. Radiolabeling of PAMAM dendrimers conjugated to a pyridine-N-oxide DOTA analog with ¹¹¹In: Optimization of reaction conditions and biodistribution. Journal of pharmaceutical and biomedical analysis. 2011 Nov; 56(3):505-12. doi: 10.1016/j.jpba.2011.06.009. [PMID: 21757312]
  • Manal K Abdel-Rahman. Can apricot kernels fatty acids delay the atrophied hepatocytes from progression to fibrosis in dimethylnitrosamine (DMN)-induced liver injury in rats?. Lipids in health and disease. 2011 Jul; 10(?):114. doi: 10.1186/1476-511x-10-114. [PMID: 21736706]
  • V E Kataev, I Iu Strobykina, O V Andreeva, B F Garifullin, R R Sharipova, V F Mironov, R V Chestnova. [Synthesis and antituberculosis activity of the derivatives of glycoside steviolbioside from the plant Stevia rebaudiana and diterpenoid isosteviol containing hydrazone, hydrazide and pyridinoyl moieties]. Bioorganicheskaia khimiia. 2011 Jul; 37(4):542-51. doi: 10.1134/s1068162011030095. [PMID: 22096997]
  • Yann-Lii Leu, Chih-Lung Lin, Ping-Chung Kuo. Constituents from Senecio scandens and their antioxidant bioactivity. Archives of pharmacal research. 2011 Mar; 34(3):377-82. doi: 10.1007/s12272-011-0304-z. [PMID: 21547668]
  • Yan Jia, Ji Jing, Yang Bai, Zhen Li, Lande Liu, Jian Luo, Mingyao Liu, Huaqing Chen. Amelioration of experimental autoimmune encephalomyelitis by plumbagin through down-regulation of JAK-STAT and NF-κB signaling pathways. PloS one. 2011; 6(10):e27006. doi: 10.1371/journal.pone.0027006. [PMID: 22066025]
  • Oliver Fiehn, W Timothy Garvey, John W Newman, Kerry H Lok, Charles L Hoppel, Sean H Adams. Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women. PloS one. 2010 Dec; 5(12):e15234. doi: 10.1371/journal.pone.0015234. [PMID: 21170321]
  • Frederikke G Malinovsky, Peter Brodersen, Berthe Katrine Fiil, Lea Vig McKinney, Stephan Thorgrimsen, Martina Beck, H Bjørn Nielsen, Stefano Pietra, Cyril Zipfel, Silke Robatzek, Morten Petersen, Daniel Hofius, John Mundy. Lazarus1, a DUF300 protein, contributes to programmed cell death associated with Arabidopsis acd11 and the hypersensitive response. PloS one. 2010 Sep; 5(9):e12586. doi: 10.1371/journal.pone.0012586. [PMID: 20830211]
  • Lu Lin, Houhui Song, Yuetong Ji, Zhili He, Yunting Pu, Jizhong Zhou, Jian Xu. Ultrasound-mediated DNA transformation in thermophilic gram-positive anaerobes. PloS one. 2010 Sep; 5(9):e12582. doi: 10.1371/journal.pone.0012582. [PMID: 20838444]
  • Po-Chang Chiang, Nandini N Kishore, David C Thompson. Combined use of pharmacokinetic modeling and a steady-state delivery approach allows early assessment of IkappaB kinase-2 (IKK-2) target safety and efficacy. Journal of pharmaceutical sciences. 2010 Mar; 99(3):1278-87. doi: 10.1002/jps.21909. [PMID: 19743500]
  • Jun Zhang, Xianyong Yu, Pinggui Yi, Haowen Huang, Shuhui Cai, Zhong Chen. Multinuclear NMR and theoretical investigation on interactions between diperoxovanadate complex and 4-picoline-like ligands. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2010 Jan; 75(1):83-7. doi: 10.1016/j.saa.2009.09.046. [PMID: 19900838]
  • Sanghyeob Lee, Jong-Chan Hong, Woong Bae Jeon, Young-Soo Chung, Soonkee Sung, Doil Choi, Young Hee Joung, Boung-Jun Oh. The salicylic acid-induced protection of non-climacteric unripe pepper fruit against Colletotrichum gloeosporioides is similar to the resistance of ripe fruit. Plant cell reports. 2009 Oct; 28(10):1573-80. doi: 10.1007/s00299-009-0756-5. [PMID: 19701640]
  • Michael J Hearn, Michael H Cynamon, Michaeline F Chen, Rebecca Coppins, Jessica Davis, Helen Joo-On Kang, Abigail Noble, Becky Tu-Sekine, Marianne S Terrot, Daniella Trombino, Minh Thai, Eleanor R Webster, Rebecca Wilson. Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid. European journal of medicinal chemistry. 2009 Oct; 44(10):4169-78. doi: 10.1016/j.ejmech.2009.05.009. [PMID: 19524330]
  • Devinder Sandhu, I Made Tasma, Ryan Frasch, Madan K Bhattacharyya. Systemic acquired resistance in soybean is regulated by two proteins, Orthologous to Arabidopsis NPR1. BMC plant biology. 2009 Aug; 9(?):105. doi: 10.1186/1471-2229-9-105. [PMID: 19656407]
  • Benjamin Fode, Tanja Siemsen, Corinna Thurow, Ralf Weigel, Christiane Gatz. The Arabidopsis GRAS protein SCL14 interacts with class II TGA transcription factors and is essential for the activation of stress-inducible promoters. The Plant cell. 2008 Nov; 20(11):3122-35. doi: 10.1105/tpc.108.058974. [PMID: 18984675]
  • S Lakshmi Narayana, K Janardhan Reddy, S Adi Narayana Reddy, Y Sarala, A Varada Reddy. A highly sensitive spectrophotometric determination of micro amounts of vanadium(V) in environmental and alloy samples by using 3,4-dihydroxybenzaldehydeisonicotinoylhydrazone (3,4-DHBINH). Environmental monitoring and assessment. 2008 Sep; 144(1-3):341-9. doi: 10.1007/s10661-007-9997-3. [PMID: 17968666]
  • Yiguang Jin, Shufeng Chen, Rui Xin, Yisheng Zhou. Monolayers of the lipid derivatives of isoniazid at the air/water interface and the formation of self-assembled nanostructures in water. Colloids and surfaces. B, Biointerfaces. 2008 Jul; 64(2):229-35. doi: 10.1016/j.colsurfb.2008.01.023. [PMID: 18329860]
  • Ming-Kui Zhong, Zhen Shi, Li-Min Zhou, Juan Gao, Zhao-Hui Liao, Wei Wang, Xing-Ya Gao, Guo-Qing Zhu. Regulation of cardiac sympathetic afferent reflex by GABA(A) and GABA(B) receptors in paraventricular nucleus in rats. The European journal of neuroscience. 2008 Jun; 27(12):3226-32. doi: 10.1111/j.1460-9568.2008.06261.x. [PMID: 18554298]
  • K K Dholwani, A K Saluja, A R Gupta, D R Shah. A review on plant-derived natural products and their analogs with anti-tumor activity. Indian journal of pharmacology. 2008 Mar; 40(2):49-58. doi: 10.4103/0253-7613.41038. [PMID: 21279166]
  • Martin Fenske. Determination of cortisol in human plasma by thin-layer chromatography and fluorescence derivatization with isonicotinic acid hydrazide. Journal of chromatographic science. 2008 Jan; 46(1):1-3. doi: 10.1093/chromsci/46.1.1. [PMID: 18218180]
  • Vincentius A Halim, Lennart Eschen-Lippold, Simone Altmann, Mandy Birschwilks, Dierk Scheel, Sabine Rosahl. Salicylic acid is important for basal defense of Solanum tuberosum against Phytophthora infestans. Molecular plant-microbe interactions : MPMI. 2007 Nov; 20(11):1346-52. doi: 10.1094/mpmi-20-11-1346. [PMID: 17977146]
  • Adriaan E Basson, Ian A Dubery. Identification of a cytochrome P450 cDNA (CYP98A5) from Phaseolus vulgaris, inducible by 3,5-dichlorosalicylic acid and 2,6-dichloro isonicotinic acid. Journal of plant physiology. 2007 Apr; 164(4):421-8. doi: 10.1016/j.jplph.2006.02.006. [PMID: 16584810]
  • Hiroyuki Kawahigashi, Sakiko Hirose, Takayoshi Iwai, Yuko Ohashi, Wataru Sakamoto, Masahiko Maekawa, Yasunobu Ohkawa. Chemically induced expression of rice OSB2 under the control of the OsPR1.1 promoter confers increased anthocyanin accumulation in transgenic rice. Journal of agricultural and food chemistry. 2007 Feb; 55(4):1241-7. doi: 10.1021/jf062339w. [PMID: 17253710]
  • Nazmul H Bhuiyan, Akira Hamada, Nana Yamada, Vandna Rai, Takashi Hibino, Teruhiro Takabe. Regulation of betaine synthesis by precursor supply and choline monooxygenase expression in Amaranthus tricolor. Journal of experimental botany. 2007; 58(15-16):4203-12. doi: 10.1093/jxb/erm278. [PMID: 18182425]
  • Dominique Maciejewski-Lenoir, Jeremy G Richman, Yaron Hakak, Ibragim Gaidarov, Dominic P Behan, Daniel T Connolly. Langerhans cells release prostaglandin D2 in response to nicotinic acid. The Journal of investigative dermatology. 2006 Dec; 126(12):2637-46. doi: 10.1038/sj.jid.5700586. [PMID: 17008871]
  • Zhi-Gang Qian, Zhen-Jiang Zhao, Yufang Xu, Xuhong Qian, Jian-Jiang Zhong. Novel synthetic 2,6-dichloroisonicotinate derivatives as effective elicitors for inducing the biosynthesis of plant secondary metabolites. Applied microbiology and biotechnology. 2006 Jun; 71(2):164-7. doi: 10.1007/s00253-005-0151-2. [PMID: 16172887]
  • Suzana Borovic, Gunars Tirzitis, Dace Tirzite, Ana Cipak, Gholam A Khoschsorur, Georg Waeg, Franz Tatzber, Mira Scukanec-Spoljar, Neven Zarkovic. Bioactive 1,4-dihydroisonicotinic acid derivatives prevent oxidative damage of liver cells. European journal of pharmacology. 2006 May; 537(1-3):12-9. doi: 10.1016/j.ejphar.2006.03.004. [PMID: 16600211]
  • F A Sirgel, J S Maritz, A Venter, G Langdon, P J Smith, P R Donald. Monitoring the ingestion of anti-tuberculosis drugs by simple non-invasive methods. International journal of pharmaceutics. 2006 Jan; 307(2):182-7. doi: 10.1016/j.ijpharm.2005.09.033. [PMID: 16303269]
  • T Scior, S J Garcés-Eisele. Isoniazid is not a lead compound for its pyridyl ring derivatives, isonicotinoyl amides, hydrazides, and hydrazones: a critical review. Current medicinal chemistry. 2006; 13(18):2205-19. doi: 10.2174/092986706777935249. [PMID: 16918349]
  • Souleiman El Balkhi, Pierre Sandouk, Martine Galliot-Guilley. Determination of ethylene thiourea in urine by HPLC-DAD. Journal of analytical toxicology. 2005 May; 29(4):229-33. doi: 10.1093/jat/29.4.229. [PMID: 15975251]
  • Thomas Wittek, Kathleen Wittek, Manfred Fürll. [Effects of a single dose of dexamethasone-21-isonicotinate on the phagocytosis performance of neutrophilic granulocytes and monocytes in periparturient dairy cows]. Berliner und Munchener tierarztliche Wochenschrift. 2005 Mar; 118(3-4):140-9. doi: ". [PMID: 15803762]
  • Marcos Marques da Silva Paula, Claus Tröger Pich, Fabrícia Petronilho, Lilian Batista Drei, Martina Rudnicki, Marcos Roberto de Oliveira, José Cláudio Fonseca Moreira, João Antônio Pegas Henriques, César Vittorio Franco, Felipe Dal Pizzol. Antioxidant activity of new ruthenium compounds. Redox report : communications in free radical research. 2005; 10(3):139-43. doi: 10.1179/135100005x38897. [PMID: 16156952]
  • Jaber S Mossa, Farouk S El-Feraly, Ilias Muhammad. Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide. Phytotherapy research : PTR. 2004 Nov; 18(11):934-7. doi: 10.1002/ptr.1420. [PMID: 15597311]
  • R Jorritsma, J Thanasak, M Houweling, J P T M Noordhuizen, K E Müller. Effects of a single dose of dexamethasone-21-isonicotinate on the metabolism of heifers in early lactation. The Veterinary record. 2004 Oct; 155(17):521-3. doi: 10.1136/vr.155.17.521. [PMID: 15551926]
  • Christof Geigerseder, Richard F G Doepner, Andrea Thalhammer, Annette Krieger, Artur Mayerhofer. Stimulation of TM3 Leydig cell proliferation via GABA(A) receptors: a new role for testicular GABA. Reproductive biology and endocrinology : RB&E. 2004 Mar; 2(?):13. doi: 10.1186/1477-7827-2-13. [PMID: 15040802]
  • M M Ghoneim, K Y el-Baradie, A Tawfik. Electrochemical behavior of the antituberculosis drug isoniazid and its square-wave adsorptive stripping voltammetric estimation in bulk form, tablets and biological fluids at a mercury electrode. Journal of pharmaceutical and biomedical analysis. 2003 Nov; 33(4):673-85. doi: 10.1016/s0731-7085(03)00311-x. [PMID: 14623593]
  • Yuelin Zhang, Mark J Tessaro, Michael Lassner, Xin Li. Knockout analysis of Arabidopsis transcription factors TGA2, TGA5, and TGA6 reveals their redundant and essential roles in systemic acquired resistance. The Plant cell. 2003 Nov; 15(11):2647-53. doi: 10.1105/tpc.014894. [PMID: 14576289]
  • A Dmitriev, M Tena, J Jorrin. Systemic acquired resistance in sunflower (Helianthus annuus L.). TSitologiia i genetika. 2003 May; 37(3):9-15. doi: . [PMID: 12945177]
  • Michael Dalgaard Mikkelsen, Bent Larsen Petersen, Erich Glawischnig, Anders Bøgh Jensen, Erik Andreasson, Barbara Ann Halkier. Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways. Plant physiology. 2003 Jan; 131(1):298-308. doi: 10.1104/pp.011015. [PMID: 12529537]
  • Piotr Rusiński, Zbigniew Kołaciński. [Acute poisoning with selected hepatotoxic agents: biochemistry of toxic effect, clinical symptoms and treatment]. Przeglad lekarski. 2003; 60(4):210-7. doi: ". [PMID: 14569886]
  • W Hartung, R G Ratcliffe. Utilization of glycine and serine as nitrogen sources in the roots of Zea mays and Chamaegigas intrepidus. Journal of experimental botany. 2002 Dec; 53(379):2305-14. doi: 10.1093/jxb/erf092. [PMID: 12432023]
  • Fengming Song, Robert M Goodman. OsBIMK1, a rice MAP kinase gene involved in disease resistance responses. Planta. 2002 Oct; 215(6):997-1005. doi: 10.1007/s00425-002-0794-5. [PMID: 12355160]
  • Han Suk Kim, Terrence P Delaney. Over-expression of TGA5, which encodes a bZIP transcription factor that interacts with NIM1/NPR1, confers SAR-independent resistance in Arabidopsis thaliana to Peronospora parasitica. The Plant journal : for cell and molecular biology. 2002 Oct; 32(2):151-63. doi: 10.1046/j.1365-313x.2001.01411.x. [PMID: 12383081]
  • Hideo Nakashita, Michiko Yasuda, Masanori Nishioka, Satoru Hasegawa, Yuko Arai, Masakazu Uramoto, Shigeo Yoshida, Isamu Yamaguchi. Chloroisonicotinamide derivative induces a broad range of disease resistance in rice and tobacco. Plant & cell physiology. 2002 Jul; 43(7):823-31. doi: 10.1093/pcp/pcf097. [PMID: 12154146]
  • Han Suk Kim, Terrence P Delaney. Arabidopsis SON1 is an F-box protein that regulates a novel induced defense response independent of both salicylic acid and systemic acquired resistance. The Plant cell. 2002 Jul; 14(7):1469-82. doi: 10.1105/tpc.001867. [PMID: 12119368]
  • Uwe Conrath, Corné M J Pieterse, Brigitte Mauch-Mani. Priming in plant-pathogen interactions. Trends in plant science. 2002 May; 7(5):210-6. doi: 10.1016/s1360-1385(02)02244-6. [PMID: 11992826]
  • Huub J J M Rennen, Julliëtte E van Eerd, Wim J G Oyen, Frans H M Corstens, D Scott Edwards, Otto C Boerman. Effects of coligand variation on the in vivo characteristics of Tc-99m-labeled interleukin-8 in detection of infection. Bioconjugate chemistry. 2002 Mar; 13(2):370-7. doi: 10.1021/bc015579k. [PMID: 11906276]
  • Jan M Lucht, Brigitte Mauch-Mani, Henry-York Steiner, Jean-Pierre Metraux, John Ryals, Barbara Hohn. Pathogen stress increases somatic recombination frequency in Arabidopsis. Nature genetics. 2002 Mar; 30(3):311-4. doi: 10.1038/ng846. [PMID: 11836502]
  • Gojen N Bordoloi, Babita Kumari, Arijit Guha, Debajit Thakur, Manabjyoti Bordoloi, Monoj K Roy, Tarun C Bora. Potential of a novel antibiotic, 2-methylheptyl isonicotinate, as a biocontrol agent against fusarial wilt of crucifers. Pest management science. 2002 Mar; 58(3):297-302. doi: 10.1002/ps.457. [PMID: 11975177]
  • G J Rairdan, N M Donofrio, T P Delaney. Salicylic acid and NIM1/NPR1-independent gene induction by incompatible Peronospora parasitica in arabidopsis. Molecular plant-microbe interactions : MPMI. 2001 Oct; 14(10):1235-46. doi: 10.1094/mpmi.2001.14.10.1235. [PMID: 11605963]
  • K Z Shen, S W Johnson. Potentiation of GABA(A) receptor agonists by GABA uptake inhibitors in the rat ventral midbrain. European journal of pharmacology. 2001 Sep; 428(1):1-7. doi: 10.1016/s0014-2999(01)01218-3. [PMID: 11779025]
  • T B Creczynski-Pasa, V R Bonetti, A Beirith, K Ckless, M Konzen, I Seifriz, M S Paula, C V Franco, D Wilhelm Filho, J B Calixto. Complexes trans-[RuCl(2)(nic)(4)] and trans-[RuCl(2)(i-nic)(4)] as free radical scavengers. Journal of inorganic biochemistry. 2001 Sep; 86(2-3):587-94. doi: 10.1016/s0162-0134(01)00222-7. [PMID: 11566331]
  • C Pillonel. Identification of a 2,6-dichloroisonicotinic-acid-sensitive protein kinase from tobacco by affinity chromatography on benzothiadiazole-sepharose and NIM-metal chelate adsorbent. Pest management science. 2001 Aug; 57(8):676-82. doi: 10.1002/ps.347. [PMID: 11517720]
  • K Sasaki, T Tatsuno, M Nakamura, A Anazawa, T Imazawa, O Utsunomiya, S Terasawa, H Osada, M Kaneko, M Toyoda. [Method-performance studies of notified analytical method for inabenfide]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan. 2001 Aug; 42(4):269-72. doi: 10.3358/shokueishi.42.269. [PMID: 11817144]
  • R Subramaniam, D Desveaux, C Spickler, S W Michnick, N Brisson. Direct visualization of protein interactions in plant cells. Nature biotechnology. 2001 Aug; 19(8):769-72. doi: 10.1038/90831. [PMID: 11479572]
  • E N Bum, M Schmutz, C Meyer, A Rakotonirina, M Bopelet, C Portet, A Jeker, S V Rakotonirina, H R Olpe, P Herrling. Anticonvulsant properties of the methanolic extract of Cyperus articulatus (Cyperaceae). Journal of ethnopharmacology. 2001 Jul; 76(2):145-50. doi: 10.1016/s0378-8741(01)00192-1. [PMID: 11390127]
  • M C Gennaro, R Calvino, C Abrigo. Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids. Journal of chromatography. B, Biomedical sciences and applications. 2001 Apr; 754(2):477-86. doi: 10.1016/s0378-4347(01)00037-8. [PMID: 11339291]
  • U Schaffrath, F Zabbai, R Dudler. Characterization of RCI-1, a chloroplastic rice lipoxygenase whose synthesis is induced by chemical plant resistance activators. European journal of biochemistry. 2000 Oct; 267(19):5935-42. doi: 10.1046/j.1432-1327.2000.01660.x. [PMID: 10998053]
  • M Rauscher, A L Adám, S Wirtz, R Guggenheim, K Mendgen, H B Deising. PR-1 protein inhibits the differentiation of rust infection hyphae in leaves of acquired resistant broad bean. The Plant journal : for cell and molecular biology. 1999 Sep; 19(6):625-33. doi: 10.1046/j.1365-313x.1999.00545.x. [PMID: 10571848]
  • Z H He, I Cheeseman, D He, B D Kohorn. A cluster of five cell wall-associated receptor kinase genes, Wak1-5, are expressed in specific organs of Arabidopsis. Plant molecular biology. 1999 Apr; 39(6):1189-96. doi: 10.1023/a:1006197318246. [PMID: 10380805]
  • J P Kamat, T P Devasagayam. Nicotinamide (vitamin B3) as an effective antioxidant against oxidative damage in rat brain mitochondria. Redox report : communications in free radical research. 1999; 4(4):179-84. doi: 10.1179/135100099101534882. [PMID: 10658823]
  • A Molina, J Görlach, S Volrath, J Ryals. Wheat genes encoding two types of PR-1 proteins are pathogen inducible, but do not respond to activators of systemic acquired resistance. Molecular plant-microbe interactions : MPMI. 1999 Jan; 12(1):53-8. doi: 10.1094/mpmi.1999.12.1.53. [PMID: 9885193]
  • J M Manners, I A Penninckx, K Vermaere, K Kazan, R L Brown, A Morgan, D J Maclean, M D Curtis, B P Cammue, W F Broekaert. The promoter of the plant defensin gene PDF1.2 from Arabidopsis is systemically activated by fungal pathogens and responds to methyl jasmonate but not to salicylic acid. Plant molecular biology. 1998 Dec; 38(6):1071-80. doi: 10.1023/a:1006070413843. [PMID: 9869413]
  • A Guevara-García, L López-Ochoa, J López-Bucio, J Simpson, L Herrera-Estrella. A 42 bp fragment of the pmas1' promoter containing an ocs-like element confers a developmental, wound- and chemically inducible expression pattern. Plant molecular biology. 1998 Nov; 38(5):743-53. doi: 10.1023/a:1006004430138. [PMID: 9862492]
  • A Guo, J Durner, D F Klessig. Characterization of a tobacco epoxide hydrolase gene induced during the resistance response to TMV. The Plant journal : for cell and molecular biology. 1998 Sep; 15(5):647-56. doi: 10.1046/j.1365-313x.1998.00241.x. [PMID: 9778847]
  • M N Ritta, J C Calamera, D E Bas. Occurrence of GABA and GABA receptors in human spermatozoa. Molecular human reproduction. 1998 Aug; 4(8):769-73. doi: 10.1093/molehr/4.8.769. [PMID: 9733434]
  • Z H He, D He, B D Kohorn. Requirement for the induced expression of a cell wall associated receptor kinase for survival during the pathogen response. The Plant journal : for cell and molecular biology. 1998 Apr; 14(1):55-63. doi: 10.1046/j.1365-313x.1998.00092.x. [PMID: 9681026]
  • O Melnyk, P Chaurand, C Rommens, H Drobecq, J M Wieruszeski, B Spengler, H Gras-Masse. Identification of a sequence-dependent reversible acylation of tosylarginine in a peptidyl-resin reacted with isonicotinyl p-nitrophenylcarbonate. The journal of peptide research : official journal of the American Peptide Society. 1998 Mar; 51(3):188-93. doi: 10.1111/j.1399-3011.1998.tb01215.x. [PMID: 9531421]
  • J Shah, F Tsui, D F Klessig. Characterization of a salicylic acid-insensitive mutant (sai1) of Arabidopsis thaliana, identified in a selective screen utilizing the SA-inducible expression of the tms2 gene. Molecular plant-microbe interactions : MPMI. 1997 Jan; 10(1):69-78. doi: 10.1094/mpmi.1997.10.1.69. [PMID: 9002272]
  • C Dominguez-Perrot, P Feltz, M O Poulter. Recombinant GABAA receptor desensitization: the role of the gamma 2 subunit and its physiological significance. The Journal of physiology. 1996 Nov; 497 ( Pt 1)(?):145-59. doi: 10.1113/jphysiol.1996.sp021756. [PMID: 8951718]
  • NULL. A controlled trial of a 4-weekly supplement of rifampicin, pyrazinamide and streptomycin in the continuation phase of a 7-month daily chemotherapy regimen for pulmonary tuberculosis. Tanzania/British Medical Research Council Collaborative Investigation. South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde. 1996 Aug; 86(8):960-5. doi: NULL. [PMID: 8823423]
  • J Durner, D F Klessig. Inhibition of ascorbate peroxidase by salicylic acid and 2,6-dichloroisonicotinic acid, two inducers of plant defense responses. Proceedings of the National Academy of Sciences of the United States of America. 1995 Nov; 92(24):11312-6. doi: 10.1073/pnas.92.24.11312. [PMID: 7479986]