What is the IUPAC name for Bryostatin 1?

The IUPAC (International Union of Pure and Applied Chemistry) name for Bryostatin 1 is (1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,20R,23R,25S)-25-Acetoxy-1,11,20-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^3,7^.1^11,15^]nonacos-8-en-12-yl (2E,4E)-2,4-octadienoate. This systematic chemical name precisely describes the molecule's complex structure according to established nomenclature rules.

What is the CAS Registry Number assigned to Bryostatin 1?

The CAS Registry Number for Bryostatin 1 is 83314-01-6. This number serves as a unique identifier for the chemical substance across scientific literature and databases.

What is the chemical formula for Bryostatin 1?

The chemical formula for Bryostatin 1 is C47H68O17. This formula indicates that each molecule contains 47 carbon atoms, 68 hydrogen atoms, and 17 oxygen atoms.

What is the molar mass of Bryostatin 1?

The molar mass of Bryostatin 1 is approximately 905.044 grams per mole (g/mol). Molar mass is a fundamental property representing the mass of one mole of a substance.

Under what standard conditions are the properties listed in the Bryostatin 1 infobox assumed to be valid?

The properties listed in the Bryostatin 1 infobox are assumed to be valid under standard state conditions. These conditions are defined as 25 degrees Celsius (77 degrees Fahrenheit) and a pressure of 100 kilopascals (kPa), ensuring consistency for comparative data.

What are bryostatins, and what is their general chemical classification?

Bryostatins are a group of macrolide lactones. Macrolides are large molecules characterized by a macrocyclic lactone ring, and lactones are a class of organic compounds that are cyclic esters.

From what marine organism are bryostatins derived?

Bryostatins are derived from the marine organism *Bugula neritina*. This organism is a type of bryozoan, commonly known as a moss animal, which typically lives in colonies attached to surfaces in marine environments.

Who was instrumental in collecting the initial samples of *Bugula neritina* for anticancer drug discovery research that led to the identification of bryostatins?

Jack Rudloe was instrumental in collecting the initial samples of *Bugula neritina*. These samples were subsequently provided to Jack L. Hartwell's anticancer drug discovery group at the National Cancer Institute (NCI), initiating the research into bryostatins.

What is the primary biological mechanism of action for bryostatins?

Bryostatins are potent modulators of protein kinase C (PKC). Protein kinase C is a family of enzymes that play a critical role in intracellular signal transduction pathways, influencing various cellular processes.

What are some of the significant medical conditions for which bryostatins have been studied?

Bryostatins have been investigated in clinical trials for several medical conditions, including their use as anti-cancer agents, anti-AIDS/HIV agents, and in the treatment of Alzheimer's disease. Their ability to modulate protein kinase C underlies these potential therapeutic applications.

What specific biological effect is Bryostatin 1 known for being a potent modulator of?

Bryostatin 1 is specifically known as a potent modulator of protein kinase C (PKC). PKC is a key enzyme involved in regulating cell growth, differentiation, and other vital cellular functions.

Why was Bryostatin 1 advanced into clinical trials?

Bryostatin 1 was advanced into clinical trials because it demonstrated significant activity in laboratory tests using cells and in studies involving model animals. These preclinical findings suggested potential therapeutic benefits that warranted further investigation in humans.

What was the overall outcome of the clinical trials conducted for cancer treatment using bryostatin?

Despite more than thirty clinical trials being conducted for cancer treatment, using bryostatin both alone and in combination with other therapies, it did not demonstrate a sufficiently favorable risk-to-benefit ratio. Consequently, it was not advanced further for cancer treatment development.

For which neurological condition did bryostatin show enough promise in animal models to initiate a Phase II clinical trial by 2010?

Bryostatin showed sufficient promise in animal models of Alzheimer's disease to warrant the initiation of a Phase II clinical trial by 2010. This suggested potential efficacy in addressing aspects of the disease.

Which institute sponsored the initial Phase II clinical trial for bryostatin in Alzheimer's disease?

The Blanchette Rockefeller Neurosciences Institute sponsored the initial Phase II clinical trial investigating bryostatin for Alzheimer's disease. This institute is dedicated to research on neurological disorders.

What company was founded by scientists from the Blanchette Rockefeller Neurosciences Institute to further investigate bryostatin for Alzheimer's disease?

Scientists from the Blanchette Rockefeller Neurosciences Institute founded a company named Neurotrope to further investigate bryostatin for Alzheimer's disease. Neurotrope subsequently launched additional clinical trials for the condition.

When were preliminary results released for a clinical trial involving bryostatin in Alzheimer's disease patients?

Preliminary results from a clinical trial involving bryostatin in patients with Alzheimer's disease were released in 2017. These results offered early insights into the compound's performance in human trials.

In addition to cancer and Alzheimer's disease, what other medical condition has been studied in relation to bryostatin?

Bryostatin has also been studied in individuals with HIV (Human Immunodeficiency Virus). Research has explored its potential effects and applications in the context of HIV infection.

Who is credited with the initial isolation of Bryostatin 1, and from which organism was it extracted?

George Pettit is credited with the initial isolation of Bryostatin 1. It was extracted from the marine bryozoan species *Bugula neritina*, based on research stemming from samples originally provided by Jack Rudloe to the National Cancer Institute.

In what year was the chemical structure of bryostatin 1 determined?

The chemical structure of bryostatin 1 was determined in 1982. Identifying the precise structure is a fundamental step in understanding a molecule's properties and potential applications.

By 2010, approximately how many different types of bryostatins had been identified and isolated?

As of 2010, approximately 20 different bryostatins had been isolated. This indicates that bryostatin is not a single compound but rather a family of related molecules.

What is the primary challenge that makes extracting bryostatins from their natural source, *Bugula neritina*, unviable for large-scale production?

The primary challenge is the extremely low concentration of bryostatins within the bryozoans. It requires approximately one tonne of the raw marine organism to extract just one gram of bryostatin, making this method impractical for producing the quantities needed for widespread use.

Why has the total synthesis of bryostatins been a difficult endeavor?

The total synthesis of bryostatins has proven difficult due to their significant structural complexity. Constructing these intricate molecules from simpler chemical precursors requires highly advanced and multi-step synthetic strategies.

Which specific bryostatins have had their total synthesis reported in scientific literature?

Total syntheses have been reported for bryostatins 1, 2, 3, 7, 9, and 16. This demonstrates considerable progress in synthetic organic chemistry in replicating these complex natural products.

Whose total synthesis of bryostatin 1 is noted as being the shortest reported to date?

The total synthesis of bryostatin 1 reported by Wender and colleagues is noted as the shortest synthesis of any bryostatin reported to date. This achievement signifies a notable advancement in synthetic efficiency for this class of compounds.

What alternative approach, besides direct extraction or total synthesis, is being explored to provide a practical supply of bryostatins?

The preparation of structurally simpler synthetic analogs is being explored as a practical alternative. These analogs are designed to replicate the biological activity and potency of the natural bryostatins, potentially offering a more feasible route for clinical applications.

In which organism does the biosynthesis of bryostatins occur?

Bryostatin biosynthesis occurs within the marine invertebrate *Bugula neritina*. It is understood that bacterial symbionts residing within this organism are responsible for producing the bryostatin compounds.

What type of enzyme system is responsible for bryostatin biosynthesis in *Bugula neritina*?

Bryostatin biosynthesis is carried out through a type I polyketide synthase (PKS) cluster, specifically designated as 'bry'. Polyketide synthases are large, multi-domain enzyme complexes essential for synthesizing many complex natural products.

What is the specific role of the enzyme BryR in the bryostatin biosynthetic pathway?

BryR functions as a secondary metabolism homolog of HMG-CoA synthase. Within the bryostatin pathway, BryR catalyzes the critical beta-branching step, which involves facilitating an aldol reaction between different molecular components.

What specific reaction does BryR catalyze during the beta-branching step in bryostatin biosynthesis?

BryR catalyzes an aldol reaction between the alpha-carbon of a BryU unit attached to an acyl carrier protein (ACP-a) and the beta-ketone of another acyl carrier protein (ACP-d). This reaction is analogous to the beta-branching reactions seen in primary metabolism.

What is the function of BryU acetyl-ACP (ACP-d) in the initial stages of bryostatin biosynthesis?

The initial step involves loading a malonyl unit onto a discrete BryU ACP-d. This loaded molecule then participates in the subsequent beta-branching reaction catalyzed by BryR, forming a key intermediate in the pathway.

What are the functions of BryT, BryA, and BryB in the bryostatin pathway after the initial beta-branching step?

Following beta-branching, BryT, which is a homolog of enoyl-CoA hydratase, performs a dehydration step. BryA is involved in O-methylation, and BryB facilitates double bond isomerization. These modifications collectively lead to the formation of the vinyl methylester moieties found in natural bryostatins.

What roles do BryC and BryD play in the final stages of bryostatin production?

BryC and BryD are responsible for further molecular extension, the closure of the pyran ring, and the final cyclization of the intermediate product. These enzymes are crucial for assembling the complete, complex structure of the bryostatin molecule.

What observation was made regarding the conversion of ACP-d in the presence of BryR during biosynthesis studies?

Studies observed that ACP-d conversion to its holo-ACP-d form occurred prior to the beta-branching reaction when BryR was present. BryR exhibited high specificity for ACP-d only after this conversion had taken place.

How do the substrates utilized in the bryostatin pathway, particularly those bound to proteins, differ from those typically found in primary metabolism?

A key difference lies in the substrate binding. BryR in the bryostatin pathway shows specificity for protein-bound acyl carrier proteins (ACPs), specifically after ACP-d is converted to holo-ACP-d. In contrast, homologs of HMG-CoA synthase found in primary metabolism typically act on substrates linked to Coenzyme A, not ACPs.

What does the image titled 'B. Neritina biosynthetic pathway for bryostatins' depict?

The image depicts the biosynthetic pathway for bryostatins within the organism *Bugula neritina*. This visual representation illustrates the sequence of enzymatic reactions and molecular transformations involved in the natural production of these compounds by the organism's bacterial symbionts.

What is the significance of the *Bugula neritina* organism in the context of bryostatin research?

The *Bugula neritina* organism is significant because it is the natural source from which bryostatins are derived. These complex molecules are produced by bacterial symbionts living within this marine bryozoan.

What is the historical context of bryostatin research, particularly regarding its discovery for potential medical use?

Bryostatin research began in the 1960s when samples of *Bugula neritina* were collected and provided to the National Cancer Institute (NCI) for anticancer drug discovery. This initiative, led by Jack L. Hartwell, aimed to identify novel therapeutic agents from natural marine sources.

What does the term 'macrolide lactone' signify in the chemical classification of bryostatins?

The term 'macrolide lactone' indicates that bryostatins belong to a class of compounds characterized by a large macrocyclic ring structure that includes a lactone functional group. A lactone is a cyclic ester, formed when a hydroxyl group and a carboxyl group within the same molecule react to form an ester linkage and close the ring.

What are the potential therapeutic applications that have driven research into bryostatins?

Research into bryostatins has been driven by their potential therapeutic applications, primarily as anti-cancer agents, anti-HIV/AIDS agents, and treatments for Alzheimer's disease. These investigations are based on their potent biological activities, particularly their modulation of protein kinase C.

What is the role of protein kinase C (PKC) in cellular processes?

Protein kinase C (PKC) is a family of enzymes that play a crucial role in intracellular signal transduction. They are involved in regulating a wide variety of cellular functions, including cell growth, differentiation, metabolism, and immune responses, by phosphorylating target proteins.

What challenges are associated with the *in vivo* production of bryostatins by *Bugula neritina*?

The primary challenge associated with *in vivo* production is the extremely low yield of bryostatins from the organism. Approximately one tonne of *Bugula neritina* is required to isolate just one gram of bryostatin, making natural extraction impractical for large-scale pharmaceutical production.

What is the significance of reporting total syntheses for specific bryostatins like Bryostatin 1, 2, 3, 7, 9, and 16?

Reporting total syntheses demonstrates the feasibility of chemically constructing these complex molecules in the laboratory from basic starting materials. This achievement offers potential alternative routes for production, potentially overcoming the limitations and low yields associated with natural extraction.

What is the 'standard state' reference used for chemical properties in the infobox?

The 'standard state' is a reference condition used for comparing chemical properties consistently. It is defined as a temperature of 25°C (77°F) and a pressure of 100 kPa, ensuring that measurements are taken under uniform, specified environmental conditions.

What does the term 'modulator' imply regarding bryostatin's effect on protein kinase C?

The term 'modulator' suggests that bryostatins can influence the activity of protein kinase C in various ways, not necessarily just activating or inhibiting it. They can alter the enzyme's function, its interactions with other molecules, or its localization within the cell, thereby affecting cellular signaling pathways.

What is the implication of bryostatin not showing a 'good enough risk:benefit ratio' in cancer trials?

This statement implies that during clinical trials for cancer, the observed side effects, toxicity, or adverse events associated with bryostatin were considered too significant in proportion to the therapeutic benefits achieved. This unfavorable balance prevented its further development as a cancer treatment.

What is a 'polyketide synthase' (PKS) cluster in the context of biosynthesis?

A polyketide synthase (PKS) cluster is a set of genes that encode large, multi-domain enzymes responsible for synthesizing polyketides, a diverse group of natural products. Bryostatins are synthesized via a type I PKS cluster, indicating a specific mechanism involving large, modular enzyme complexes.

What is the significance of BryR being a homolog of HMG-CoA synthase?

BryR's classification as a homolog of HMG-CoA synthase suggests a shared evolutionary origin or functional similarity in catalyzing reactions involving beta-ketoacyl substrates. However, BryR operates within the specialized bryostatin pathway, acting on acyl carrier protein-bound substrates, which differs from the Coenzyme A-bound substrates typically used by HMG-CoA synthase in primary metabolism.

What are 'acyl carrier proteins' (ACPs) in the context of biosynthesis?

Acyl carrier proteins (ACPs) are small protein molecules that serve as essential carriers for acyl groups, such as acetyl or malonyl groups, during the synthesis of fatty acids and polyketides. They are integral components of the enzymatic machinery involved in building these carbon-based molecules.

Bryostatin: Nature's Complex Macrolide Unveiled

An exploration into the structure, biological activity, and synthesis of a potent marine natural product.

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Bryostatin 1
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Names
IUPAC name	(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,20R,23R,25S)-25-Acetoxy-1,11,20-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.1^3,7.1^11,15]nonacos-8-en-12-yl (2E,4E)-2,4-octadienoate
Identifiers
CAS Number	83314-01-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:88353
ChEMBL	ChEMBL449158
ChemSpider	27022418
DrugBank	DB11752
KEGG	C05149
PubChem CID	5280757
UNII	37O2X55Y9E
InChI	InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-42-31(24-41(53)58-9)23-34-25-37(28(2)48)61-43(54)36(50)17-16-33-26-38(59-29(3)49)45(6,7)46(55,63-33)27-35-21-30(22-40(52)57-8)20-32(60-35)18-19-44(4,5)47(42,56)64-34/h12-15,18-19,22,24,28,32-38,42,48,50,55-56H,10-11,16-17,20-21,23,25-27H2,1-9H3/b13-12+,15-14+,19-18+,30-22+,31-24+/t28-,32+,33-,34+,35+,36-,37-,38+,42+,46+,47-/m1/s1 Key: XYXASLYZTKBYQJ-OAUMSBLFSA-N 1: InChI=1/C47H68O17/c1-10-11-12-13-14-15-39(51)62-42-31(24-41(53)58-9)23-34-25-37(28(2)48)61-43(54)36(50)17-16-33-26-38(59-29(3)49)45(6,7)46(55,63-33)27-35-21-30(22-40(52)57-8)20-32(60-35)18-19-44(4,5)47(42,56)64-34/h12-15,18-19,22,24,28,32-38,42,48,50,55-56H,10-11,16-17,20-21,23,25-27H2,1-9H3/b13-12+,15-14+,19-18+,30-22+,31-24+/t28-,32+,33-,34+,35+,36-,37-,38+,42+,46+,47-/m1/s1 Key: XYXASLYZTKBYQJ-OAUMSBLFBY
SMILES	1: CCC/C=C/C=C/C(=O)O[C@H]1/C(=C/C(=O)OC)/C[C@H]2C[C@@H](OC(=O)[C@@H](CC[C@@H]3C[C@@H](C([C@@](O3)(C[C@@H]4C/C(=C/C(=O)OC)/C[C@@H](O4)/C=C/C([C@@]1(O2)O)(C)C)O)(C)C)OC(=O)C)O)[C@@H](C)O
Properties
Chemical formula	C₄₇H₆₈O₁₇
Molar mass	905.044 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

What is Bryostatin?

Marine Origin

Bryostatins constitute a class of complex macrolide lactones, originally isolated from the marine invertebrate *Bugula neritina*. These organisms, often referred to as sea moss or sea lace, harbor bacterial symbionts that are believed to be the true producers of these intricate molecules. The initial discovery and subsequent research into bryostatins were driven by their potential as anticancer agents.

Molecular Mechanism

Bryostatins are recognized as potent modulators of protein kinase C (PKC) enzymes. PKC plays a critical role in numerous cellular signaling pathways, influencing cell growth, differentiation, and survival. By interacting with PKC, bryostatins can profoundly affect cellular behavior, making them subjects of intense investigation for various therapeutic applications.

Therapeutic Potential

The unique biological activity of bryostatins has led to their investigation in clinical trials for several challenging conditions. Research has explored their efficacy as anti-cancer agents, treatments for HIV/AIDS, and even as potential therapies for neurodegenerative diseases like Alzheimer's disease, highlighting their broad pharmacological scope.

Biological Effects

Protein Kinase C Modulation

Bryostatin 1, the most studied congener, acts as a potent activator of protein kinase C (PKC) isoforms. This interaction is central to its biological effects, influencing downstream signaling cascades involved in cell proliferation, apoptosis, and differentiation. This modulation makes bryostatins attractive candidates for diseases where PKC signaling is dysregulated.

Clinical Trial History

Over the past decades, bryostatins have undergone extensive preclinical and clinical evaluation. More than thirty clinical trials have been conducted, investigating their use in various cancers, including solid tumors and hematological malignancies, both as monotherapy and in combination regimens. While demonstrating biological activity, the risk-benefit profile has historically limited their advancement in oncology.

Neurodegenerative and Viral Applications

Beyond oncology, bryostatins have shown promise in other therapeutic areas. Preclinical studies in animal models of Alzheimer's disease indicated potential benefits, leading to Phase II clinical trials. Furthermore, their activity against HIV has also been explored, suggesting a versatile therapeutic profile stemming from their fundamental interaction with cellular signaling pathways.

Chemistry & Synthesis

Natural Product Isolation

Bryostatin 1 was first isolated in the 1960s by George Pettit from extracts of the marine bryozoan *Bugula neritina*. The process involves extracting large quantities of the organism, as the concentration of bryostatins is exceedingly low—approximately one ton of raw material is needed for just one gram of Bryostatin 1. This low yield poses significant challenges for large-scale production.

Synthetic Challenges

The complex macrocyclic structure of bryostatins has made their total synthesis a formidable challenge in organic chemistry. Despite considerable effort, only a limited number of total syntheses for various bryostatin congeners have been reported. These synthetic endeavors, while academically significant, often involve numerous steps and low overall yields, further complicating practical supply.

Key milestones in bryostatin synthesis include:

The structure of Bryostatin 1 was elucidated in 1982.
As of 2010, twenty different bryostatins had been isolated.
Total syntheses have been reported for Bryostatins 1, 2, 3, 7, 9, and 16.
Notable synthetic efforts include Wender's concise synthesis of Bryostatin 1 and Trost's atom-economical approach to Bryostatin 16.

Analogs and Future Supply

Recognizing the difficulties in natural extraction and total synthesis, researchers have focused on developing structurally simpler synthetic analogs. These analogs aim to retain the beneficial biological profile of natural bryostatins while offering a more feasible route for scalable production, potentially enabling wider clinical application.

Biosynthesis Pathway

Polyketide Synthase Machinery

Within *Bugula neritina*, bryostatin biosynthesis is orchestrated by a Type I polyketide synthase (PKS) gene cluster, denoted as 'bry'. This complex enzymatic machinery is responsible for constructing the macrocyclic core of the bryostatin molecule through a series of iterative condensation reactions.

Key Enzymatic Steps

Central to the pathway is the enzyme BryR, a homolog of HMG-CoA synthase, which catalyzes a crucial β-branching step. This involves the condensation of an acyl carrier protein (ACP)-linked donor with an acceptor molecule. Subsequent enzymatic modifications, including dehydration, methylation, isomerization, and cyclization, are carried out by other domains within the PKS cluster (e.g., BryT, BryA, BryB, BryC, BryD) to yield the final bryostatin structure.

The biosynthesis involves intricate steps:

Loading: Malonyl units are loaded onto discrete ACP domains (e.g., BryU ACP-d).
β-Branching: BryR catalyzes the formation of a β-branched carbon chain, a key step differentiating it from primary metabolism.
Elongation & Modification: Subsequent domains perform dehydration, methylation, and isomerization.
Cyclization: Final steps involve ring closure and formation of the characteristic macrocyclic lactone structure.

The specificity of these enzymatic interactions, particularly BryR's reliance on a converted ACP-d, highlights the sophisticated regulation within the PKS pathway.

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References

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Bryostatin: Nature's Complex Macrolide Unveiled

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What is Bryostatin? ℹ️

🌊 Marine Origin

⚙️ Molecular Mechanism

🔬 Therapeutic Potential

Biological Effects 🧬

🎯 Protein Kinase C Modulation

🧪 Clinical Trial History

🧠 Neurodegenerative and Viral Applications

Chemistry & Synthesis 🧪

🌿 Natural Product Isolation

🏗️ Synthetic Challenges

💡 Analogs and Future Supply

Biosynthesis Pathway 🌱

🔗 Polyketide Synthase Machinery

酶 Key Enzymatic Steps

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📜 Important Notice

Dive in with Flashcard Learning!

What is Bryostatin?

Marine Origin

Molecular Mechanism

Therapeutic Potential

Biological Effects

Protein Kinase C Modulation

Clinical Trial History

Neurodegenerative and Viral Applications

Chemistry & Synthesis

Natural Product Isolation

Synthetic Challenges

Analogs and Future Supply

Biosynthesis Pathway

Polyketide Synthase Machinery

Key Enzymatic Steps

Teacher's Corner

True or False?

Test Your Knowledge!

Gamer's Corner

Discover other topics to study!

References

Feedback & Support

Disclaimer

Important Notice