endo-BCN-PEG3-PFP ester - CAS 2101206-48-6

endo-BCN-PEG3-PFP ester - CAS 2101206-48-6 Catalog number: BADC-00416

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Category
ADCs Linker
Product Name
endo-BCN-PEG3-PFP ester
CAS
2101206-48-6
Catalog Number
BADC-00416
Molecular Formula
C26H30F5NO7
Molecular Weight
563.51
endo-BCN-PEG3-PFP ester

Ordering Information

Catalog Number Size Price Quantity
BADC-00416 -- $--
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Synonyms
perfluorophenyl 1-(bicyclo[6.1.0]non-4-yn-9-yl)-3-oxo-2,7,10,13-tetraoxa-4-azahexadecan-16-oate
Canonical SMILES
C1CC2C(C2COC(=O)NCCOCCOCCOCCC(=O)OC3=C(C(=C(C(=C3F)F)F)F)F)CCC#C1
InChI
InChI=1S/C26H30F5NO7/c27-20-21(28)23(30)25(24(31)22(20)29)39-19(33)7-9-35-11-13-37-14-12-36-10-8-32-26(34)38-15-18-16-5-3-1-2-4-6-17(16)18/h16-18H,3-15H2,(H,32,34)
InChIKey
KXWYFDXVBMIXQH-UHFFFAOYSA-N
Appearance
Soild powder
Purity
98%
Shipping
Room temperature
Storage
-20°C

endo-BCN-PEG3-PFP ester, a versatile bifunctional linker molecule, finds extensive utility in bioconjugation and chemical biology. Here are four key applications of endo-BCN-PEG3-PFP ester creatively:

Bioconjugation: Positioned as a cornerstone in scientific pursuits, endo-BCN-PEG3-PFP ester emerges as a crucial player in coupling biomolecules like proteins, peptides, and antibodies through the intricate art of click chemistry. The BCN group engages in selective reactions with azide-functionalized molecules, giving birth to robust triazole linkages. This coupling maneuver, renowned for its efficacy, enables the meticulous assembly of functional bioconjugates tailored for a myriad of diagnostic and therapeutic ventures.

Drug Delivery: Pioneering targeted drug delivery innovations, endo-BCN-PEG3-PFP ester assumes a pivotal role in crafting precision drug delivery systems. By conjugating therapeutic agents to targeting entities, such as ligands or antibodies, this ester facilitates the accurate transport of drugs to specific cellular destinations. This focused delivery mechanism not only enhances treatment efficacy but also mitigates unintended off-target effects and toxicit.

Surface Modification: Venturing into the realm of surface engineering, endo-BCN-PEG3-PFP ester emerges as a crucial contributor in functionalizing surfaces for a myriad of biomedical devices and biosensor applications. Through the strategic attachment of designated biomolecules to azide-functionalized surfaces, this versatile ester enables the creation of bioactive surfaces imbued with tailored characteristics. These modified surfaces have the potential to enhance biocompatibility, elevate sensor sensitivity, or facilitate intricate cell culture experiments, emphasizing the transformative impact of surface modification in biological inquiries.

Chemical Biology Research: Within the dynamic domain of chemical biology, endo-BCN-PEG3-PFP ester assumes a pivotal role in exploring and manipulating biological systems. Harnessing this ester to label biomolecules with fluorophores or affinity tags empowers researchers to precisely monitor and isolate specific proteins or cellular components. This methodical approach, integral to unraveling intricate biological pathways and pinpointing promising drug targets, underscores the indispensable nature of endo-BCN-PEG3-PFP ester in advancing our understanding of the complex mechanisms governing biological processes.

1. Catalytic antibodies
A Tramontano, R A Lerner, K D Janda Science . 1986 Dec 19;234(4783):1566-70. doi: 10.1126/science.3787261.
Monoclonal antibodies elicited to haptens that are analogs of the transition state for hydrolysis of carboxylic esters behaved as enzymic catalysts with the appropriate substrates. These substrates are distinguished by the structural congruence of both hydrolysis products with haptenic fragments. The haptens were potent inhibitors of this esterolytic activity, in agreement with their classification as transition state analogs. Mechanisms are proposed to account for the different chemical behavior of these antibodies with two types of ester substrates. The generation of an artificial enzyme through transition state stabilization by antibodies was thus demonstrated. These studies indicate a potentially general approach to catalyst design.
2. [Esters and stereoisomers]
V Nigrovic, C Diefenbach, H Mellinghoff Anaesthesist . 1997 Apr;46(4):282-6. doi: 10.1007/s001010050402.
This review discusses concepts of isomers, stereoisomers, chirality, and enantiomers as applied to drugs used in anaesthesia. The inhalational anaesthetics enflurane and isoflurane are examples of stereoisomers. A chiral centre is formed when a carbon or quaternary nitrogen atom is connected to four different atoms. A molecule with one chiral centre is then present in one of two possible configurations termed enantiomers. A racemate is a mixture of both enantiomers in equal proportions. Many of the drugs used in anaesthesia are racemic mixtures (the inhalation anaesthetics, local anaesthetics, ketamine, and others). The shape of the atracurium molecule is comparable to that of a dumb-bell:the two isoquinoline groups representing the two bulky ends connected by an aliphatic chain. In each isoquinoline group there are two chiral centres, one formed by a carbon and the other by a quaternary nitrogen atom. From a geometric point of view, the connections from the carbon atom to a substituted benzene ring and from the quaternary nitrogen to the aliphatic chain may point in the same direction (cis configuration) or in opposite directions (trans configuration). The two isoquinoline groups in atracurium are paired in three geometric configurations: cis-cis, trans-trans, or cis-trans. However, the two chiral centres allow each isoquinoline group to exist in one of four stereoisometric configurations. In the symmetrical atracurium molecule, the number of possible stereoisomers is limited to ten. Among these, 1 R-cis, 1'R-cis atracurium was isolated and its pharmacologic properties studied. This isomer, named cis-atracurium, offers clinical advantages over the atracurium mixture, principally due to the lack of histamine-releasing propensity and the higher neuromuscular blocking potency. The ester groups appear in one of two steric configurations true and reverse esters. In the true esters, oxygen is positioned between the nitrogen atom and the carbonyl group, while in the reverse esters in its positioned on the other side of the carbonyl group. True esters, suxamethonium and mivacurium, are hydrolysed by the enzyme plasma cholinesterase (butyrylcholinesterase), albeit at different rates. The more rapid degradation of suxamethonium is responsible for its fast onset and short duration of action in comparison with mivacurium. The reverse esters, atracurium, cisatracurium, and remifentanil, are hydrolysed by nonspecific esterases in plasma (carboxyesterases). Remifentanil is hydrolysed rapidly; the degradation leads to its inactivation and short duration of action. Cis-atracurium is preferentially degraded and inactivated by a process known as Hofmann elimination. In a second step, one of the degradation products, the monoester acrylate, is hydrolysed by a nonspecific esterase.
3. [Evaluation of the Oral Absorption of Ester-type Prodrugs]
Kayoko Ohura Yakugaku Zasshi . 2020;140(3):369-376. doi: 10.1248/yakushi.19-00225.
The first-pass hydrolysis of oral ester-type prodrugs in the liver and intestine is mediated mainly by hCE1 and hCE2 of the respective predominant carboxylesterase (CES) isozymes. In order to provide high blood concentrations of the parent drugs, it is preferable that prodrugs are absorbed as an intact ester in the intestine, then rapidly converted to active parent drugs by hCE1 in the liver. In the present study, we designed a prodrug of fexofenadine (FXD) as a model parent drug that is resistant to hCE2 but hydrolyzed by hCE1, utilizing the differences in catalytic characteristics of hCE1 and hCE2. In order to precisely predict the intestinal absorption of an FXD prodrug candidate, we developed a novel high-throughput system by modifying Caco-2 cells. Further, we evaluated species differences and aging effects in the intestinal and hepatic hydrolysis of prodrugs to improve the estimation of in vivo first-pass hydrolysis of ester-type prodrugs. Consequently, it was possible to design a hepatotropic prodrug utilizing the differences in tissue distribution and substrate specificity of CESs. In addition, we successfully established three useful in vitro systems for predicting the intestinal absorption of hCE1 substrate using Caco-2 cells. However, some factors involved in estimating the bioavailability of prodrugs in human, such as changes in recognition of drug transporters by esterification, and species differences of the first-pass hydrolysis, should be comprehensively considered in prodrug development.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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