7313-32-8

Basic information

• Product Name: Cyclopentadiene dimer
• CAS NO: 7313-32-8
• Molecular Formula: C10H12
• Molecular Weight: 132.20228
• Mol File: 7313-32-8.mol
• Article Data: 310

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopentadiene dimer(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentadiene dimer(7313-32-8)
• EPA Substance Registry System: Cyclopentadiene dimer(7313-32-8)

Safety Data

• Hazardous Substances Data: 7313-32-8(Hazardous Substances Data)

Upstream product

• 142-29-0 cyclopentene 
• 71-36-3 butan-1-ol 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 
• 2684-60-8 2-diazopropane 
• 2101-87-3 p-methoxy-phenylazide 
• 14548-31-3 hex-1-en-5-yne 
• 128375-79-1 prop-2-enyl 2-thiabicyclo<2.2.1>hept-5-ene-endo/exo-3-carboxylate 
• 128375-80-4 but-3-enyl 2-thiabicyclo<2.2.1>hept-5-ene-endo/exo-3-carboxylate 
• 128399-12-2 pent-4-enyl 2-thiabicyclo<2.2.1>hept-5-ene-endo/exo-3-carboxylate 
• 122902-50-5 5-(cyclopentadienylidenemethyl)bicyclo<2.2.1>hept-2-ene 
• 37734-07-9 methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate 
• 98230-14-9 hexacyclo<5.4.1.0^2.6.0^3.10.0^5.9.0^8.11>dodecane-4,12-dione 
• 74428-26-5 4,4a,8,8a-Tetrahydro-1H-1,4-methano-naphthalen-5-one 
• 83927-49-5 Acetic acid 8-((1S,3S,7R)-4,4-dioxo-4λ⁶-thia-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl)-octyl ester 

Downstream Products

• 6143-30-2 5-phenylbicyclo[2.2.1]hept-2-ene 
• 57467-58-0 2-phenyl-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethano-naphthalene 
• 941567-71-1 (1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol 
• 68326-89-6 4,7-dimethyl-5,6-diphenyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-8-one 
• 100532-30-7 cyclohexyl-norborn-5-en-2-yl ether 
• 59259-40-4 (+/-)-3endo-(4-chloro-phenyl)-norborn-5-ene-2exo-carboxylic acid 
• 59259-40-4 (+/-)-3exo-(4-chloro-phenyl)-norborn-5-ene-2endo-carboxylic acid 
• 54705-50-9 4,9-dibenzoyl-3a,4,9,9a-tetrahydro-1H-cyclopenta[b]quinoxaline 
• 92549-26-3 3-endo-benzoylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid 
• 92549-26-3 3-exo-benzoylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 
• 132752-51-3 (3-chloro-norborn-5-en-2-yl)-p-tolyl ketone 
• 569-45-9 3exo-(4-nitro-phenyl)-norborn-5-ene-2endo-sulfonyl fluoride 
• 102448-26-0 (1RS)-5endo,6endo-[(RS,RS)-bis-(toluene-4-sulfinyl)]-norborn-2-ene 
• 114888-66-3 (1RS)-5endo,6endo-[(RS,RS)-bis-(4-methoxy-benzenesulfinyl)]-norborn-2-ene 

Relevant articles and documents

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This contribution describes the design and synthesis of multifunctional micelles based on amphiphilic brush block copolymers (BBCPs) for imaging and selective drug delivery of natural anticancer compounds. Well-defined BBCPs were synthesized via one-pot multi-step sequential grafting-through ring-opening metathesis polymerization (ROMP) of norbornene-based macroinitiators. The norbornenes employed contain a poly(ethylene glycol) methyl ether chain, an alkyl bromide chain, and/or a near-infrared (NIR) fluorescent cyanine dye. After block copolymerization, post-polymerization transformations using bromide-azide substitution, followed by the strain-promoted azide-alkyne cycloaddition (SPAAC) allowed for the functionalization of the BBCPs with the piplartine (PPT) moiety, a natural product with well-documented cytotoxicity against cancer cell lines, via an ester linker between the drug and the polymer side chain. The amphiphilic BBCPs self-assembled in aqueous media into nano-sized spherical micelles with neutral surface charges, as confirmed by dynamic light scattering analysis and transmission electron microscopy. During self-assembly, paclitaxel (PTX) could be effectively encapsulated into the hydrophobic core to form stable PTX-loaded micelles with high loading capacities and encapsulation efficiencies. The NIR fluorescent dye-containing micelles exhibited remarkable photophysical properties, excellent colloidal stability under physiological conditions, and a pH-induced disassembly under slightly acidic conditions, allowing for the release of the drug in a controlled manner. The in vitro studies demonstrated that the micelles without the drug (blank micelles) are biocompatible at concentrations of up to 1 mg mL-1 and present a high cellular internalization capacity toward MCF-7 cancer cells. The drug-functionalized micelles showed in vitro cytotoxicity comparable to free PPT and PTX against MCF-7 and PC3 cancer cells, confirming efficient drug release into the tumor environment upon cellular internalization. Furthermore, the drug-functionalized micelles exhibited higher selectivity than the pristine drugs and preferential cellular uptake in human cancer cell lines (MCF-7 and PC3) when compared to the normal breast cell line (MCF10A). This study provides an efficient strategy for the development of versatile polymeric nanosystems for drug delivery and image-guided diagnostics. Notably, the easy functionalization of BBCP side chains via SPAAC opens up the possibility for the preparation of a library of multifunctional systems containing other drugs or functionalities, such as target groups for recognition.

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