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19916-73-5

19916-73-5 structure
19916-73-5 structure
  • Name: O6-Benzylguanine
  • Chemical Name: 6-phenylmethoxy-7H-purin-2-amine
  • CAS Number: 19916-73-5
  • Molecular Formula: C12H11N5O
  • Molecular Weight: 241.249
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-09-10 15:09:17
  • Modify Date: 2024-01-03 18:30:28
  • O6-Benzylguanine, a guanine analog, is the DNA repair enzyme O6-alkylguanine-DNA alkyltransferase (MGMT/AGT) inhibitor. O6-Benzylguanine acts as an AGT substrate, which transfers its benzyl group to the AGT cysteine residue, thereby irreversibly inactivating AGT and preventing DNA repair. O6-Benzylguanine induces tumor cell apoptosis. Antineoplastic activity[1][2].
Name 6-phenylmethoxy-7H-purin-2-amine
Synonyms O(6)-Benzylguanine
7H-purin-2-amine, 6-(phenylmethoxy)-
O6-Benzylguanine
2-amino-6-(phenylmethoxy)-9H-purine
O(6)-bGua
2-Amino-6-benzyloxy-9H-purine
O-6-Benzylguanine
6-Benzyloxy guanine
6-(Benzyloxy)-3H-purin-2-amine
2-Amino-6-(benzyloxy)purine
6-O-Benzylguanine
9H-Purin-2-amine, 6-(phenylmethoxy)-
6-(benzyloxy)guanine
O-Benzylguanine
6-(phenylmethoxy)-9H-purin-2-amine
MFCD00269931
amino-6-(phenylmethoxy)-9H-purine
6-(Benzyloxy)-7H-purin-2-amine
Description O6-Benzylguanine, a guanine analog, is the DNA repair enzyme O6-alkylguanine-DNA alkyltransferase (MGMT/AGT) inhibitor. O6-Benzylguanine acts as an AGT substrate, which transfers its benzyl group to the AGT cysteine residue, thereby irreversibly inactivating AGT and preventing DNA repair. O6-Benzylguanine induces tumor cell apoptosis. Antineoplastic activity[1][2].
Related Catalog
In Vitro The L3.6pl cells are relatively sensitive to O6-Benzylguanine (24-72 hours) in a dose- and time-dependent manner. The IC50 is 50 μg (at 48 hours)[2]. O6-Benzylguanine (50 μg; 48 hours) modulates p53 downstream target protein expression, induces apoptosis, and decreases cell proliferation[2]. O6-Benzylguanine (50 μg; 48 hours) significantly decreases the MGMT transcriptional activity in L3.6pl[2]. Western Blot Analysis[2] Cell Line: L3.6pl and PANC1 cells Concentration: 50 μg Incubation Time: 48 hours Result: Expressions of O6 methyl guanine DNA methyl transferase (MGMT), cyclin B1, cyclin B2, cyclin A, p53, and ki-67 were decreased, whereas p21 was increased. The levels of cyto C and caspase 9 were increased, whereas the levels of PARP1 protein were decreased. RT-PCR[2] Cell Line: L3.6pl cells Concentration: 50 μg Incubation Time: 48 hours Result: Decreased the MGMT transcriptional activity in L3.6pl.
In Vivo O6-Benzylguanine (100 μg; i.p.; daily for 35 days) inhibits pancreatic cancer cell growth and increases pancreatic cell sensitivity to Gemcitabine (100 mg/kg)[2]. O6-Benzylguanine inhibits pancreatic cancer cell proliferation and induces tumor cell apoptosis in vivo[2]. Animal Model: Male athymic nude mice (NCI-nu) (bearing human pancreatic cancer L3.6pl cells)[2] Dosage: 100 μg Administration: i.p; daily for 35 days Result: Significantly decreased median tumor volume and weight.
References

[1]. Rabik CA, Njoku MC, Dolan ME. Inactivation of O6-alkylguanine DNA alkyltransferase as a means to enhance chemotherapy. Cancer Treat Rev. 2006;32(4):261‐276.

[2]. Konduri, Santhi D et al. Blockade of MGMT expression by O6 benzyl guanine leads to inhibition of pancreatic cancer growth and induction of apoptosis. Clinical cancer research : an official journal of the American Association for Cancer Research vol. 15,19 (2009): 6087-95.
Density 1.4±0.1 g/cm3
Boiling Point 621.4±63.0 °C at 760 mmHg
Melting Point 193(dec.)
Molecular Formula C12H11N5O
Molecular Weight 241.249
Flash Point 329.6±33.7 °C
Exact Mass 241.096359
PSA 89.71000
LogP 1.95
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.743
Storage condition -20°C Freezer
Water Solubility methanol: 20 mg/mL
Material Safety Data Sheet
Section1. Identification of the substance
O6-Benzylguanine
Product Name:
Synonyms:
Section2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315:Causes skin irritation
H319:Causes serious eye irritation
H335:May cause respiratory irritation
P261:Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340:IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405:Store locked up
Section3. Composition/information on ingredients.
O6-Benzylguanine
Ingredient name:
CAS number:19916-73-5
Section4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:
Section5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.
Section6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution:Wear approved mask/respirator
Hand precaution:Wear suitable gloves/gauntlets
Skin protection:Wear suitable protective clothing
Eye protection:Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.
Section7. Handling and storage
Handling:This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage:Store in closed vessels.
Section8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.
Section9. Physical and chemical properties
Not specified
Appearance:
Boiling point:No data
Melting point:No data
Flash point:No data
Density:No data
Molecular formula:C12H11N5O
Molecular weight:241.3
Section10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.
Section11. Toxicological information
No data.
Section12. Ecological information
No data.
Section13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.
Section14. Transportation information
Non-harzardous for air and ground transportation.
Section15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

SECTION 16 - ADDITIONAL INFORMATION
N/A
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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