Daxian Shan

Works (5)

Updated: July 5th, 2023 16:04

2000 journal article

A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis

Chemical & Pharmaceutical Bulletin, 48(2), 238–244.

By: D. Shan, A. Zheng, C. Ballard, W. Wang, R. Borchardt & B. Wang

Source: NC State University Libraries
Added: August 6, 2018

1999 article

Coumarinic Acid-Based Cyclic Prodrugs of Opioid Peptides that Exhibit Metabolic Stability to Peptidases and Excellent Cellular Permeability

Gudmundsson, O. S., Pauletti, G. M., Wang, W., Shan, D., Zhang, H., Wang, B., & Borchardt, R. T. (1999, January 1). Pharmaceutical Research.

By: O. Gudmundsson*, G. Pauletti *, W. Wang n, D. Shan n, H. Zhang  n, B. Wang n, R. Borchardt*

author keywords: esterase-sensitive prodrugs; peptide delivery; opioid peptides; Caco-2 cells; membrane permeability; chemical and enzymatic stability
MeSH headings : Animals; Caco-2 Cells; Cell Membrane Permeability; Coumaric Acids / metabolism; Endorphins / metabolism; Enzyme Stability; Humans; Male; Molecular Sequence Data; Peptide Hydrolases / metabolism; Peptides, Cyclic / metabolism; Prodrugs; Rats; Rats, Sprague-Dawley
topics (OpenAlex): Chemical Synthesis and Analysis; Molecular spectroscopy and chirality; Asymmetric Synthesis and Catalysis
TL;DR: The cell permeation characteristics and the chemical and enzymatic stability of coumarinic acid-based cyclic pro-drugs were evaluated andcyclic prodrugs exhibited significantly greater stability against peptidase metabolism than did [Leu5]-enkephalin and DADLE. (via Semantic Scholar)
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Source: Web Of Science
Added: August 6, 2018

1999 article

Synthesis and evaluation of the physicochemical properties of esterase‐sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers

Wang, B., Wang, W., Zhang, H., Shan, D., Nimkar, K., Gudmundsson, O., … Borchardt, R. T. (1999, April 1). Journal of Peptide Research.

By: B. Wang n, W. Wang n, H. Zhang*, D. Shan*, K. Nimkar*, O. Gudmundsson *, S. Gangwar *, T. Siahaan *, R. Borchardt*

author keywords: membrane transport; opioid peptide; physicochemical properties; prodrugs
MeSH headings : Amino Acid Sequence; Cell Membrane Permeability / drug effects; Chemical Phenomena; Chemistry, Physical; Coumaric Acids / chemistry; Enkephalin, Leucine / chemistry; Enkephalin, Leucine / pharmacology; Enkephalin, Leucine-2-Alanine / chemistry; Enkephalin, Leucine-2-Alanine / pharmacology; Esterases / metabolism; Membranes, Artificial; Models, Biological; Opioid Peptides / chemical synthesis; Opioid Peptides / chemistry; Opioid Peptides / metabolism; Peptides, Cyclic / chemical synthesis; Peptides, Cyclic / chemistry; Peptides, Cyclic / metabolism; Permeability; Phenylpropionates / chemistry; Prodrugs / chemical synthesis; Prodrugs / chemistry; Prodrugs / metabolism; Prodrugs / pharmacology; Structure-Activity Relationship
topics (OpenAlex): Chemical Synthesis and Analysis; Neuropeptides and Animal Physiology; Receptor Mechanisms and Signaling
TL;DR: The enhanced cellular permeation of the cyclic prodrugs is apparently due to the alteration of their lipophilicity and hydrogen bonding potential, but not their molecular sizes. (via Semantic Scholar)
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Source: Web Of Science
Added: August 6, 2018

1998 article

A Redox-Sensitive Resin Linker for the Solid Phase Synthesis of C-Terminal Modified Peptides

Zheng, A., Shan, D., & Wang, B. (1998, December 9). The Journal of Organic Chemistry.

By: A. Zheng n, D. Shan n & B. Wang n

topics (OpenAlex): Chemical Synthesis and Analysis; Click Chemistry and Applications; Peptidase Inhibition and Analysis
TL;DR: A redox-sensitive resin linker is developed for the synthesis of C-terminal-modified peptides by taking advantage of a "trimethyl lock"-facilitated lactonization reaction, which allows for the ready cleavage of the linker under mild conditions. (via Semantic Scholar)
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Source: Web Of Science
Added: August 6, 2018

1997 article

Prodrug Strategies Based on Intramolecular Cyclization Reactions

Shan, D., Nicolaou, M. G., Borchardt, R. T., & Wang, B. (1997, July 1). Journal of Pharmaceutical Sciences.

By: D. Shan n, M. Nicolaou, R. Borchardt & B. Wang n

MeSH headings : Animals; Carbamates / chemical synthesis; Carbamates / metabolism; Coumarins / chemical synthesis; Cyclization; Humans; Lactones / chemical synthesis; Mustard Compounds / chemical synthesis; Mustard Compounds / metabolism; Prodrugs / chemical synthesis; Prodrugs / metabolism
topics (OpenAlex): Chemical Synthesis and Analysis; Carbohydrate Chemistry and Synthesis; Asymmetric Synthesis and Catalysis
TL;DR: Several new prodrug systems for amines, alcohols, and peptides are reviewed, which takes advantage of several facile intramolecular cyclization reactions, that permit separate manipulation of the release kinetics independent of the structural features of the drug moiety. (via Semantic Scholar)
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Source: Web Of Science
Added: August 6, 2018

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