4.6 Review

Marine Cyanobacteria as Sources of Lead Anticancer Compounds: A Review of Families of Metabolites with Cytotoxic, Antiproliferative, and Antineoplastic Effects

Related references

Note: Only part of the references are listed.
Article Plant Sciences

Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium, Hormoscilla sp

David A. Brumley et al.

Summary: Our ongoing efforts in exploring the chemical space of marine cyanobacteria have led to the discovery of two new members of the anaenamide family. These compounds, isolated from a novel cyanobacterium, show potential activation of the Nrf2 pathway at noncytotoxic concentrations.

JOURNAL OF NATURAL PRODUCTS (2022)

Review Oncology

Hallmarks of Cancer: New Dimensions

Douglas Hanahan

Summary: The concept of the hallmarks of cancer is a tool for simplifying the complexity of cancer phenotypes and genotypes into basic principles. This article proposes phenotypic plasticity and disrupted differentiation as distinct hallmark capabilities, and discusses nonmutational epigenetic reprogramming and polymorphic microbiomes as enabling characteristics. Additionally, the importance of senescent cells in the tumor microenvironment is highlighted. The integrative concept of the hallmarks of cancer helps in understanding the mechanisms of cancer development and applying that knowledge to cancer medicine.

CANCER DISCOVERY (2022)

Article Neurosciences

Thallium Induces Antiproliferative and Cytotoxic Activity in Glioblastoma C6 and U373 Cell Cultures via Apoptosis and Changes in Cell Cycle

Edgar Rangel-Lopez et al.

Summary: Thallium (Tl+) is a heavy metal that exhibits cytotoxic and antiproliferative effects in glioblastoma cells. The effects of Tl+ vary between different cell lines and concentrations, with C6 cells being more sensitive than U373 cells. Tl+ also affects cell viability, cell cycle, and induces apoptosis in these cells. Neural and astrocytic primary cultures show lower sensitivity to Tl+ compared to glioblastoma cells. The combination of Tl+ and temozolamide further alters the cell cycle in glioblastoma cells. These findings suggest the potential of Tl+ as a therapeutic agent for glioblastoma.

NEUROTOXICITY RESEARCH (2022)

Article Chemistry, Multidisciplinary

Structural Determination, Total Synthesis, and Biological Activity of Iezoside, a Highly Potent Ca2+-ATPase Inhibitor from the Marine Cyanobacterium Leptochromothrix valpauliae

Naoaki Kurisawa et al.

Summary: In this study, a new SERCA inhibitor, iezoside (1), isolated from the marine cyanobacterium Leptochromothrix valpauliae, is reported. Iezoside (1) is the second-strongest SERCA inhibitor known to date, with a structure fundamentally different from any other SERCA inhibitor, and the highest potency among marine natural products (K_i 7.1 nM). The comprehensive analysis of iezoside (1), including its isolation, structural characterization supported by density functional theory (DFT) calculations and statistical analysis, total synthesis, and clarification of the mode of action of its potent antiproliferative activity (IC50 6.7 +/- 0.4 nM against HeLa cells), is described.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Isolation of Caldorazole, a Thiazole-Containing Polyketide with Selective Cytotoxicity under Glucose-Restricted Conditions

Osamu Ohno et al.

Summary: A new polyketide, Caldorazole (1), was isolated from Caldora sp., a marine cyanobacterium collected in Ishigaki Island, Okinawa, Japan. It exhibited strong cytotoxicity against tumor cells by selectively inhibiting complex I in the mitochondrial respiratory chain.

ORGANIC LETTERS (2022)

Article Pharmacology & Pharmacy

Targeting of HER/ErbB family proteins using broad spectrum Sec61 inhibitors coibamide A and apratoxin A

Soheila Kazemi et al.

Summary: Coibamide A is a potent inhibitor of HER/ErbB signaling, particularly sensitive to HER3 and EGFR. It can decrease HER2 expression through Sec61-dependent inhibition, and enhance the cytotoxic efficacy of small molecule kinase inhibitors in breast and lung cancer cells.

BIOCHEMICAL PHARMACOLOGY (2021)

Review Oncology

Targeting oncogenic Notch signaling with SERCA inhibitors

Luca Pagliaro et al.

Summary: P-type ATPase inhibitors are widely used in modern pharmacology, but clinical translation of Ca2+ -ATPase modulators remains challenging. Recent evidence suggests that SERCA inhibitors can exert anti-leukemia effects by inhibiting Notch1 signaling.

JOURNAL OF HEMATOLOGY & ONCOLOGY (2021)

Review Biotechnology & Applied Microbiology

Heterologous production of cyanobacterial compounds

Dipesh Dhakal et al.

Summary: In summary, cyanobacteria have great potential for producing new natural products, but progress in discovering these compounds has been slow due to silent biosynthetic gene clusters and difficulties with cyanobacterial strains. Heterologous expression in genetically tractable hosts is a promising approach for unlocking the discovery of new cyanobacterial natural products.

JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY (2021)

Article Chemistry, Medicinal

Novel N-Methylated Cyclodepsipeptide Prodrugs for Targeted Cancer Therapy

Chunlei Wu et al.

Summary: Researchers discovered a simplified analogue of Coibamide A and designed two novel peptide-drug conjugates, with one showing better drug release in vitro and significant tumor growth suppression in mice-bearing human tumor xenografts, indicating great potential in cancer drug discovery.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Review Chemistry, Medicinal

Synthesis and Biological Activities of Cyclodepsipeptides of Aurilide Family from Marine Origin

Synthia Michon et al.

Summary: Aurilides, a class of depsipeptides found mainly in marine cyanobacteria, have shown strong cytotoxicity against various cancer cell lines. Numerous studies on aurilides have emerged since 1996, summarizing both their biological activities and total syntheses of natural compounds and synthetic analogues.

MARINE DRUGS (2021)

Review Biochemistry & Molecular Biology

Cyanobacteria as Natural Therapeutics and Pharmaceutical Potential: Role in Antitumor Activity and as Nanovectors

Hina Qamar et al.

Summary: Cyanobacteria are considered one of the most efficient sources of bioactive secondary metabolites, with their natural compounds showing anticancer activity by inducing cytotoxicity in cancer cells through various pathways.

MOLECULES (2021)

Article Cell Biology

Long noncoding RNA LINC00518 induces radioresistance by regulating glycolysis through an miR-33a-3p/HIF-1α negative feedback loop in melanoma

Yan Liu et al.

Summary: LINC00518 is a long noncoding RNA that is highly expressed in various cancers, including cutaneous malignant melanoma (CMM), and plays a role in promoting cancer progression. In CMM, LINC00518 induces radioresistance by regulating the glycolysis pathway through a negative feedback loop involving miR-33a-3p and hypoxia-inducible factor 1 alpha (HIF-1 alpha). Knockdown of LINC00518 expression sensitizes CMM cells to radiotherapy, suggesting a potential strategy to improve treatment outcomes.

CELL DEATH & DISEASE (2021)

Article Biochemistry & Molecular Biology

Coibamide A kills cancer cells through inhibiting autophagy

Wenli Shi et al.

Summary: Coibamide A is a promising lead compound for cancer treatment due to its excellent tumor cell growth inhibitory profile and sub-nanomolar potency. It induces caspase-independent cell death and severe lysosome defects, blocking autophagosomelysosome fusion and leading to tumor cell death. These findings provide novel insights into the anti-cancer mechanism of action of Coibamide A.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2021)

Article Oncology

Cancer statistics for the year 2020: An overview

Jacques Ferlay et al.

Summary: The study briefly reviews the methods and data sources used in compiling the IARC GLOBOCAN cancer statistics for 2020 and summarizes the main results. It estimated that there were nearly 19.3 million new cancer cases and almost 10 million cancer deaths worldwide in 2020, with the most commonly diagnosed cancers being female breast cancer and lung cancer, and the most common causes of cancer death being lung cancer and liver cancer.

INTERNATIONAL JOURNAL OF CANCER (2021)

Review Chemistry, Medicinal

Cyanobacteria-From the Oceans to the Potential Biotechnological and Biomedical Applications

Shaden A. M. Khalifa et al.

Summary: Cyanobacteria produce bioactive compounds that have shown promising pharmacological activities in clinical trials, making them potential candidates for COVID-19 treatment. Large-scale synthesis of these compounds is essential to overcome issues with chemical isolation and further investigate their biological activities.

MARINE DRUGS (2021)

Review Chemistry, Medicinal

Marine Antitumor Peptide Dolastatin 10: Biological Activity, Structural Modification and Synthetic Chemistry

Gang Gao et al.

Summary: Dolastatin 10 is a marine pentapeptide derived from the Indian Ocean mollusk Dolabella auricularia, which has shown significant potency in inducing apoptosis of tumor cells. It has been developed into commercial drugs for specific lymphomas and further research using ADCs has shown promising antitumor activity with enhanced targeting and reduced systemic toxicity.

MARINE DRUGS (2021)

Article Chemistry, Medicinal

Metabolomic Characterization of a cf. Neolyngbya Cyanobacterium from the South China Sea Reveals Wenchangamide A, a Lipopeptide with In Vitro Apoptotic Potential in Colon Cancer Cells

Lijian Ding et al.

Summary: Metabolomics was used to analyze a biomass from the South China Sea, resulting in the discovery of a new natural product with potential anticancer properties. Through untargeted metabolomics and bioassay-guided fractionation, a structural proposal for a new natural product analogue was generated, providing important insights for anticancer drug discovery and synthetic analogue development.

MARINE DRUGS (2021)

Article Chemistry, Applied

Neo-debromoaplysiatoxin C, with new structural rearrangement, derived from debromoaplysiatoxin

Yang-Hua Tang et al.

NATURAL PRODUCT RESEARCH (2020)

Article Biochemistry & Molecular Biology

Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens

Mioko Kawaguchi et al.

MOLECULES (2020)

Review Biochemistry & Molecular Biology

Marine Cyanobacteria: A Source of Lead Compounds and their Clinically-Relevant Molecular Targets

Lik Tong Tan et al.

MOLECULES (2020)

Article Biochemistry & Molecular Biology

Coibamide A Targets Sec61 to Prevent Biogenesis of Secretory and Membrane Proteins

Dale Tranter et al.

ACS CHEMICAL BIOLOGY (2020)

Article Biochemistry & Molecular Biology

Largazole is a Brain-Penetrant Class I HDAC Inhibitor with Extended Applicability to Glioblastoma and CNS Diseases

Fatma H. Al-Awadhi et al.

ACS CHEMICAL NEUROSCIENCE (2020)

Article Biochemistry & Molecular Biology

Bioactivities of Lyngbyabellins from Cyanobacteria ofMooreaandOkeaniaGenera

Imam Fathoni et al.

MOLECULES (2020)

Article Chemistry, Organic

Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta

Shimpei Sumimoto et al.

ORGANIC LETTERS (2019)

Article Chemistry, Organic

New aplysiatoxin derivatives from the Okinawan cyanobacterium Moorea producens

Hiroshi Nagai et al.

TETRAHEDRON (2019)

Review Chemistry, Medicinal

Natural Products from Cyanobacteria: Focus on Beneficial Activities

Justine Demay et al.

MARINE DRUGS (2019)

Review Pharmacology & Pharmacy

Advances in exploring the therapeutic potential of marine natural products

Xiao Liang et al.

PHARMACOLOGICAL RESEARCH (2019)

Article Food Science & Technology

Oscillatoxin I: A New Aplysiatoxin Derivative, from a Marine Cyanobacterium

Hiroshi Nagai et al.

TOXINS (2019)

Article Plant Sciences

Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium Moorea producens

Hao-Bing Yu et al.

JOURNAL OF NATURAL PRODUCTS (2019)

Article Chemistry, Medicinal

Exploration of the carmaphycins as payloads in antibody drug conjugate anticancer agents

Jehad Almaliti et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Chemistry, Organic

Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp.

Yiwen Tao et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Medicinal

Improved Total Synthesis and Biological Evaluation of Coibamide A Analogues

Guiyang Yao et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Biotechnology & Applied Microbiology

The Swinholide Biosynthesis Gene Cluster from a Terrestrial Cyanobacterium, Nostoc sp Strain UHCC 0450

Anu Humisto et al.

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2018)

Article Plant Sciences

Serinolamides and Lyngbyabellins from an Okeania sp Cyanobacterium Collected from the Red Sea

Julie G. Petitbois et al.

JOURNAL OF NATURAL PRODUCTS (2017)

Review Oncology

Proteasome inhibitors in cancer therapy

Elisabet E. Manasanch et al.

NATURE REVIEWS CLINICAL ONCOLOGY (2017)

Article Chemistry, Medicinal

Apratoxin S10, a Dual Inhibitor of Angiogenesis and Cancer Cell Growth To Treat Highly Vascularized Tumors

Weijing Cai et al.

ACS MEDICINAL CHEMISTRY LETTERS (2017)

Article Multidisciplinary Sciences

A quantitative shRNA screen identifies ATP1A1 as a gene that regulates cytotoxicity by aurilide B

Shohei Takase et al.

SCIENTIFIC REPORTS (2017)

Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of Santacruzamate-A based analogues

Rosario Randino et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2017)

Review Oncology

Novel Therapeutic Strategies Against Cancer: Marine-derived Drugs May Be the Answer?

Maria Alessandra Gammone et al.

ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY (2016)

Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of santacruzamate A analogues for anti-proliferative and immunomodulatory activity

Samantha M. Gromek et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2016)

Article Biochemistry & Molecular Biology

Naturally Inspired Peptide Leads: Alanine Scanning Reveals an Actin-Targeting Thiazole Analogue of Bisebromoamide

Heather J. Johnston et al.

CHEMBIOCHEM (2016)

Article Plant Sciences

Bartolosides E-K from a Marine Coccoid Cyanobacterium

Tiago B. Afonso et al.

JOURNAL OF NATURAL PRODUCTS (2016)

Article Oncology

Apratoxin A Shows Novel Pancreas-Targeting Activity through the Binding of Sec 61

Kuan-Chun Huang et al.

MOLECULAR CANCER THERAPEUTICS (2016)

Review Biochemistry & Molecular Biology

Unique marine derived cyanobacterial biosynthetic genes for chemical diversity

Karin Kleigrewe et al.

NATURAL PRODUCT REPORTS (2016)

Article Chemistry, Organic

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

Kosuke Sueyoshi et al.

TETRAHEDRON (2016)

Article Biochemistry & Molecular Biology

Apratoxin Kills Cells by Direct Blockade of the Sec61 Protein Translocation Channel

Anja O. Paatero et al.

Cell Chemical Biology (2016)

Article Chemistry, Multidisciplinary

Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria

Pedro N. Leao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Biochemistry & Molecular Biology

Modular synthesis and biological activity of pyridyl-based analogs of the potent Class I Histone Deacetylase Inhibitor Largazole

Dane J. Clausen et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2015)

Article Chemistry, Medicinal

Synthesis and biological evaluation of the [D-MeAla11]-epimer of coibamide A

Ryota Nabika et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2015)

Article Medicine, Research & Experimental

Recent Advances in the Development of New Auristatins: Structural Modifications and Application in Antibody Drug Conjugates

Andreas Maderna et al.

MOLECULAR PHARMACEUTICS (2015)

Review Biochemistry & Molecular Biology

Biological targets and mechanisms of action of natural products from marine cyanobacteria

Lilibeth A. Salvador-Reyes et al.

NATURAL PRODUCT REPORTS (2015)

Article Biochemistry & Molecular Biology

Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis

Jairo Quintana et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2014)

Article Oncology

Brentuximab Vedotin

Changchun Deng et al.

CLINICAL CANCER RESEARCH (2013)

Article Plant Sciences

Apratoxin H and Apratoxin A Sulfoxide from the Red Sea Cyanobacterium Moorea producens

Christopher C. Thornburg et al.

JOURNAL OF NATURAL PRODUCTS (2013)

Article Multidisciplinary Sciences

Coibamide A Induces mTOR-Independent Autophagy and Cell Death in Human Glioblastoma Cells

Andrew M. Hau et al.

PLOS ONE (2013)

Article Multidisciplinary Sciences

Improving the coverage of the cyanobacterial phylum using diversity-driven genome sequencing

Patrick M. Shih et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2013)

Article Chemistry, Medicinal

Largazole Arrests Cell Cycle at G1 Phase and Triggers Proteasomal Degradation of E2F1 in Lung Cancer Cells

Li-Chuan Wu et al.

ACS MEDICINAL CHEMISTRY LETTERS (2013)

Article Pharmacology & Pharmacy

Brentuximab Vedotin: A New Age in the Treatment of Hodgkin Lymphoma and Anaplastic Large Cell Lymphoma

Stephanie S. Minich

ANNALS OF PHARMACOTHERAPY (2012)

Article Chemistry, Organic

Lyngbyabellins K-N from Two Palmyra Atoll Collections of the Marine Cyanobacterium Moorea bouillonii

Hyukjae Choi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Multidisciplinary Sciences

Largazole and Its Derivatives Selectively Inhibit Ubiquitin Activating Enzyme (E1)

Dana Ungermannova et al.

PLOS ONE (2012)

Review Biochemistry & Molecular Biology

Hallmarks of Cancer: The Next Generation

Douglas Hanahan et al.

Article Biochemistry & Molecular Biology

Marine Natural Product Aurilide Activates the OPA1-Mediated Apoptosis by Binding to Prohibitin

Shin-ichi Sato et al.

CHEMISTRY & BIOLOGY (2011)

Article Plant Sciences

Malyngamide 3 and Cocosamides A and B from the Marine Cyanobacterium Lyngbya majuscula from Cocos Lagoon, Guam

Sarath P. Gunasekera et al.

JOURNAL OF NATURAL PRODUCTS (2011)

Article Chemistry, Medicinal

Swinholide J, a Potent Cytotoxin from the Marine Sponge Theonella swinhoei

Simona De Marino et al.

MARINE DRUGS (2011)

Article Biochemistry & Molecular Biology

Lagunamide C, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Lyngbya majuscula

Ashootosh Tripathi et al.

PHYTOCHEMISTRY (2011)

Review Biotechnology & Applied Microbiology

Cyanobactins-ribosomal cyclic peptides produced by cyanobacteria

Kaarina Sivonen et al.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2010)

Review Biochemistry & Molecular Biology

Azole-Based Cyclic Peptides from the Sea Squirt Lissoclinum Patella: Old Scaffolds, New Avenues

Wael E. Houssen et al.

CHEMBIOCHEM (2010)

Article Plant Sciences

Caylobolide B, a Macrolactone from Symplostatin 1-Producing Marine Cyanobacteria Phormidium spp. from Florida

Lilibeth A. Salvador et al.

JOURNAL OF NATURAL PRODUCTS (2010)

Article Pharmacology & Pharmacy

Anticolon Cancer Activity of Largazole, a Marine-Derived Tunable Histone Deacetylase Inhibitor

Yanxia Liu et al.

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS (2010)

Article Pharmacology & Pharmacy

Apratoxin A Reversibly Inhibits the Secretory Pathway by Preventing Cotranslational Translocation

Yanxia Liu et al.

MOLECULAR PHARMACOLOGY (2009)

Article Chemistry, Multidisciplinary

Total synthesis and biological mode of action of largazole: A potent Class I histone deacetylase inhibitor

Albert Bowers et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp.

Kanchan Taori et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Coibamide A, a potent antiproliferative cyclic depsipeptide from the panamanian marine cyanobacterium Leptolyngbya sp.

Rebecca A. Medina et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Biochemistry & Molecular Biology

Natural combinatorial peptide libraries in cyanobacterial symbionts of marine ascidians

Mohamed S. Donia et al.

NATURE CHEMICAL BIOLOGY (2006)

Article Biochemistry & Molecular Biology

Characterization of apoptosis induced by marine natural products in non small cell lung cancer A549 cells

A. Catassi et al.

CELLULAR AND MOLECULAR LIFE SCIENCES (2006)

Article Biochemistry & Molecular Biology

A functional genomics approach to the mode of action of apratoxin A

H Luesch et al.

NATURE CHEMICAL BIOLOGY (2006)

Article Biochemistry & Molecular Biology

Dolastatin 11 conformations, analogues and pharmacophore

MA Ali et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2005)

Article Plant Sciences

Hectochlorin and morpholine derivatives from the Thai sea hare, Bursatella leachii

S Suntornchashwej et al.

JOURNAL OF NATURAL PRODUCTS (2005)

Article Multidisciplinary Sciences

Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiont of Lissoclinum patella

EW Schmidt et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2005)

Article Oncology

The molecular pharmacology of symplostatin 1: A new antimitotic dolastatin 10 analog

SL Mooberry et al.

INTERNATIONAL JOURNAL OF CANCER (2003)

Article Plant Sciences

Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly

BL Marquez et al.

JOURNAL OF NATURAL PRODUCTS (2002)

Article Biochemistry & Molecular Biology

New apratoxins of marine cyanobacterial origin from Guam and Palau

H Luesch et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2002)

Article Chemistry, Organic

Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula

JB MacMillan et al.

ORGANIC LETTERS (2002)

Article Plant Sciences

Symplostatin 3, a new dolastatin 10 analogue from the marine cyanobacterium Symploca sp VP452

H Luesch et al.

JOURNAL OF NATURAL PRODUCTS (2002)

Article Chemistry, Multidisciplinary

Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula

H Luesch et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)