Thapsigargin, Origin, Chemistry, Structure-Activity Relationships and Prodrug Development.

No abstract is available for this paper.

• Publication year

  2015

• Venue

  Current pharmaceutical design

• Publication date

  2015-10-31

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.2174/1381612821666151002112824PMID 26429715
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Targeted Prodrug Approaches for Hormone Refractory Prostate Cancer

  2015cited by this paper
• Acyloxylation of cyclic enones: synthesis of densely oxygenated guaianolides.

  2014cited by this paper
• The European Medicines Agency approval of ingenol mebutate (Picato) for the cutaneous treatment of non-hyperkeratotic, non-hypertrophic actinic keratosis in adults: Summary of the scientific assessment of the Committee for Medicinal Products for Human Use (CHMP)

  2014cited by this paper
• Trilobolide and related sesquiterpene lactones from Laser trilobum possessing immunobiological properties.

  2013cited by this paper
• Water-mediated interactions influence the binding of thapsigargin to sarco/endoplasmic reticulum calcium adenosinetriphosphatase.

  2013influential reference
• Engineering a Prostate-Specific Membrane Antigen–Activated Tumor Endothelial Cell Prodrug for Cancer Therapy

  2012cited by this paper
• Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase.

  2010influential reference
• Critical Roles of Hydrophobicity and Orientation of Side Chains for Inactivation of Sarcoplasmic Reticulum Ca2+-ATPase with Thapsigargin and Thapsigargin Analogs*

  2010influential reference
• Mechanistic insights into the inhibition of prostate specific antigen by beta-lactam class compounds.

  2008cited by this paper
• Total synthesis of five thapsigargins: guaianolide natural products exhibiting sub-nanomolar SERCA inhibition.

  2007cited by this paper
• Mechanistic insights into the inhibition of prostate specific antigen by β‐lactam class compounds

  2007cited by this paper
• Natural products as starting materials for development of second-generation SERCA inhibitors targeted towards prostate cancer cells.

  2006cited by this paper
• Toward the synthesis of thapsigargin: enantioselective synthesis of 7,11-dihydroxyguaianolides.

  2006cited by this paper
• Total synthesis of two novel subpicomolar sarco/endoplasmatic reticulum Ca2+-ATPase inhibitors designed by an analysis of the binding site of thapsigargin.

  2005cited by this paper
• Expression of prostate‐specific antigen (PSA) and human glandular kallikrein 2 (hK2) in ileum and other extraprostatic tissues

  2005cited by this paper
• The SERCA pump as a therapeutic target: Making a “smart bomb” for prostate cancer

  2005influential reference
• Thapsigargin, a histamine secretagogue, is a non-12-O-tetradecanolphorbol-13-acetate (TPA) type tumor promoter in two-stage mouse skin carcinogenesis

  2004cited by this paper
• Synthesis of the thapsigargins.

  2004cited by this paper
• Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer.

  2003influential reference
• Structural changes in the calcium pump accompanying the dissociation of calcium

  2002cited by this paper
• Design, synthesis, and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells.

  2001cited by this paper
• Thapsigargin analogues for targeting programmed death of androgen-independent prostate cancer cells.

  1999cited by this paper
• A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases.

  1998cited by this paper
• Prostate-specific antigen forms complexes with human alpha 2-macroglobulin and binds to the alpha 2-macroglobulin receptor/LDL receptor-related protein.

  1998cited by this paper
• Specific and efficient peptide substrates for assaying the proteolytic activity of prostate-specific antigen.

  1997influential reference
• Sesquiterpenoids from Thapsia species and medicinal chemistry of the thapsigargins.

  1997cited by this paper
• Characterization of prostate-specific antigen proteolytic activity on its major physiological substrate, the sperm motility inhibitor precursor/semenogelin I.

  1997cited by this paper
• Structure-activity relationships of analogues of thapsigargin modified at O-11 and O-12.

  1995cited by this paper
• SELECTIVE TRANSFORMATIONS OF THE CA2+ PUMP INHIBITOR THAPSIGARGIN

  1994influential reference
• Derivatives of thapsigargin as probes of its binding site on endoplasmic reticulum Ca2+ ATPase

  1993cited by this paper
• Prostate-specific antigen in serum occurs predominantly in complex with alpha 1-antichymotrypsin.

  1991cited by this paper
• Nortrilobolide, a New Potent Guaianolide Secretagogue from Thapsi garganica

  1991cited by this paper
• Thapsigargin, a tumor promoter, discharges intracellular Ca2+ stores by specific inhibition of the endoplasmic reticulum Ca2(+)-ATPase.

  1990influential reference
• Enzymatic activity of prostate-specific antigen and its reactions with extracellular serine proteinase inhibitors.

  1990cited by this paper
• Semenogelin, the predominant protein in human semen. Primary structure and identification of closely related proteins in the male accessory sex glands and on the spermatozoa.

  1989cited by this paper
• The Potencies of Thapsigargin and Analogues as Activators of Rat Peritoneal Mast Cells

  1986cited by this paper
• The ability of thapsigargin and thapsigargicin to activate cells involved in the inflammatory response

  1985cited by this paper
• Absolute configurations of the histamine liberating sesquiterpene lactones thapsigargin and trilobolide

  1985cited by this paper
• Structure of histamine releasing guaianolides from Thapsia species

  1984cited by this paper
• Thapsigargin and thapsigargicin, two histamine liberating sesquiterpene lactones from Thapsia garganica. X-ray analysis of the 7,11-epoxide of thapsigargin

  1982cited by this paper
• Thapsigargin, constitution of a sesquiterpene lactone histamine liberator from thapsia garganica

  1980cited by this paper
• On the mechanism of histamine release induced by thapsigargin fromThapsia garganica L.

  1979cited by this paper
• Thapsigargine and thapsigargicine, two new histamine liberators from Thapsia garganica L.

  1978cited by this paper
• On terpenes. CCXXVII. The structure of the sesquiterpenic triester lactone trilobolide

  1973cited by this paper

• Modulation of Endoplasmic Reticulum Stress in Experimental Anti-Cancer Therapy

  2025cites this paper
• Natural sesquiterpene lactones in prostate cancer therapy: mechanisms and sources

  2025cites this paper
• Recent advances in direct asymmetric reaction of furanone

  2025cites this paper
• Sesquiterpenes and prostate cancer

  2025cites this paper
• Molecular mechanism of ultrafast transport by plasma membrane Ca2+-ATPases

  2025cites this paper
• Traversing the chiral pool potential of carvone in total synthesis of natural products

  2024cites this paper
• Plant sesquiterpene lactones

  2024cites this paper
• LC3A-mediated autophagy elicits PERK-eIF2α-ATF4 axis activation and mitochondrial dysfunction: Exposing vulnerability in aggresome-positive cancer cells

  2024cites this paper
• Stereo-Differentiating Asymmetric Rh(I)-Catalyzed Pauson–Khand Reaction: A DFT-Informed Approach to Thapsigargin Stereoisomers

  2024cites this paper
• Thapsigargin and its prodrug derivatives: exploring novel approaches for targeted cancer therapy through calcium signaling disruption

  2024cites this paper
• Persianolide-A, an eudesmanolide-type sesquiterpene lactone from Artemisia kopetdaghensis, induces apoptosis by regulating ERK signaling pathways

  2024cites this paper
• Chrysin stimulates UCP1-independent thermogenesis in 3T3-L1 adipocytes and mouse model

  2024cites this paper
• Selenium preserves cytosolic-Ca^2+ homeostasis in olive callus cells during oxidative stress

  2023cites this paper
• Citrullination profile analysis reveals peptidylarginine deaminase 3 as an HSV-1 target to dampen the activity of candidate antiviral restriction factors

  2023cites this paper
• Honey bee Apis mellifera L. responses to oxidative stress induced by pharmacological and pesticidal compounds

  2023cites this paper
• β-Carotene induces UCP1-independent thermogenesis via ATP-consuming futile cycles in 3T3-L1 white adipocytes.

  2023cites this paper
• A Review on Mechanistic Insight of Plant Derived Anticancer Bioactive Phytocompounds and Their Structure Activity Relationship

  2022cites this paper
• Curcumin Stimulates UCP1-independent Thermogenesis in 3T3-L1 White Adipocytes but Suppresses in C2C12 Muscle Cells

  2022cites this paper
• Rh(I)-Catalyzed Allenic Pauson-Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity.

  2022cites this paper
• From Plant to Patient: Thapsigargin, a Tool for Understanding Natural Product Chemistry, Total Syntheses, Biosynthesis, Taxonomy, ATPases, Cell Death, and Drug Development.

  2021cites this paper
• Store-operated Ca2+ entry as a key oncogenic Ca2+ signaling driving tumor invasion-metastasis cascade and its translational potential.

  2021cites this paper
• Small molecule drug conjugates (SMDCs): an emerging strategy for anticancer drug design and discovery

  2021cites this paper
• Targeting oncogenic Notch signaling with SERCA inhibitors

  2021cites this paper
• Thapsigargin—From Traditional Medicine to Anticancer Drug

  2020influential citation
• Cell death induced by the ER stressor thapsigargin involves death receptor 5, a non-autophagic function of MAP1LC3B, and distinct contributions from unfolded protein response components

  2020cites this paper
• Antitumor activity and mechanism of costunolide and dehydrocostus lactone: Two natural sesquiterpene lactones from the Asteraceae family.

  2020cites this paper
• Comparison of the pharmacologic profiles of arginine vasopressin and oxytocin analogs at marmoset, titi monkey, macaque, and human oxytocin receptors

  2020cites this paper
• Sarco/endoplasmic reticulum calcium ATPase inhibitors: Beyond anticancer perspective.

  2020cites this paper
• The GPR120 Agonist TUG-891 Inhibits the Motility and Phagocytosis of Mouse Alveolar Macrophages

  2020cites this paper
• Comparison of the pharmacological profiles of arginine vasopressin and oxytocin analogs at marmoset, macaque, and human vasopressin 1a receptor.

  2020cites this paper
• Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications

  2020cites this paper
• Action of the insecticide cyfluthrin on Ca2+ signal transduction and cytotoxicity in human osteosarcoma cells

  2020cites this paper
• Blockade of Oncogenic NOTCH1 with the SERCA Inhibitor CAD204520 in T Cell Acute Lymphoblastic Leukemia.

  2020cites this paper
• Natural Sesquiterpene Lactones in the Prevention and Treatment of Inflammatory Disorders and cancer: A Systematic Study of this Emerging Therapeutic Approach based on Chemical and Pharmacological Aspect

  2020cites this paper
• Co-targeting Mitochondrial Ca2+ Homeostasis and Autophagy Enhances Cancer Cells' Chemosensitivity

  2020cites this paper
• Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.

  2020cites this paper
• Biological Activities of Phytochemicals in Plants

  2020cites this paper
• A Comparison of the Ability of Leu8- and Pro8-Oxytocin to Regulate Intracellular Ca2+ and Ca2+-Activated K+ Channels at Human and Marmoset Oxytocin Receptors

  2019cites this paper
• A stress-responsive enhancer induces dynamic drug resistance in acute myeloid leukemia

  2019cites this paper
• Structural modification of trilobolide for upgrading its immunobiological properties and reducing its cytotoxic action.

  2019cites this paper
• Epigenetic loss of the endoplasmic reticulum-associated degradation inhibitor SVIP induces cancer cell metabolic reprogramming.

  2019influential citation
• A Comparison of the Ability of Leu 8-and Pro 8-Oxytocin to Regulate Intracellular Ca 2 1 and Ca 2 1-Activated K 1 Channels at Human and Marmoset Oxytocin Receptors s

  2019cites this paper
• Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

  2019cites this paper
• Peptide Conjugates with Small Molecules Designed to Enhance Efficacy and Safety

  2019cites this paper
• 15-Hydroxygermacranolides as Sources of Structural Diversity: Synthesis of Sesquiterpene Lactones by Cyclization and Rearrangement Reactions. Experimental and DFT Study.

  2018cites this paper
• Divergent synthesis of thapsigargin analogs.

  2018cites this paper
• Promising anticancer drug thapsigargin: A perspective toward the total synthesis

  2018cites this paper
• Antiproliferative and Cytotoxic Activities

  2018cites this paper
• Use of a temporary immersion bioreactor system for the sustainable production of thapsigargin in shoot cultures of Thapsia garganica

  2018cites this paper
• Thapsigargin Increases IL-2 Production in T Cells at Nanomolar Concentrations

  2018cites this paper
• Endothelial Ca2+ Signaling and the Resistance to Anticancer Treatments: Partners in Crime

  2018cites this paper
• The Crosstalk of Endoplasmic Reticulum (ER) Stress Pathways with NF-κB: Complex Mechanisms Relevant for Cancer, Inflammation and Infection

  2018cites this paper
• Computationally Guided Catalyst Design in the Type I Dynamic Kinetic Asymmetric Pauson-Khand Reaction of Allenyl Acetates.

  2017cites this paper
• Calcitox-aging counterbalanced by endogenous farnesol-like sesquiterpenoids: An undervalued evolutionarily ancient key signaling pathway

  2017cites this paper
• Calcium-regulatory proteins as modulators of chemotherapy in human neuroblastoma

  2017cites this paper
• Structure/activity relationship of thapsigargin inhibition on the purified Golgi/secretory pathway Ca2+/Mn2+-transport ATPase (SPCA1a)

  2017cites this paper
• A Concise, Efficient and Scalable Total Synthesis of Thapsigargin and Nortrilobolide from (R)-(-)-Carvone.

  2017cites this paper
• Proteases in cancer drug delivery.

  2016cites this paper
• Metabolic engineering and synthetic biology of plant secondary metabolism

  2016cites this paper
• The rise of proteostasis promoters

  2016influential citation
• Demethoxycurcumin Is A Potent Inhibitor of P-Type ATPases from Diverse Kingdoms of Life

  2016cites this paper
• Digitoxin enhances the growth inhibitory effects of thapsigargin and simvastatin on ER negative human breast cancer cells.

  2016cites this paper
• Biosynthesis, regulation, and significance of cyanogenic glucosides

  2016cites this paper
• Editorial: Challenging Organic Syntheses and Pharmacological Applications of Natural Products and their Derivatives.

  2015cites this paper