temen – temen!! kali ini andy dapat pertanyaan dari temen andy yang bernama titis.

begini isi pertanyaannya:

“Ndi….tau mekanisme aspirin menghambat cyclookxigenase G?”

karena basic yang aku ketahui adalah kimia organik maka setelah aku jelasin lewat farmakologi, akan aku jelaskan melalui kimia organik

Intro

image

Aspirin adalah obat yang menghambat enzym COX (baik COX1 maupun COX2) melalui asetilasi residu dari COX. Obat ini tergolong NSAID(non steroid antiinflamatory drug).

 

image   Nah…sesungguhnya apabila kita tahu residu apa yang akan diasetilisasi oleh aspirin, jawabannya udah selesai jika berhadapan dengan dosen farmakologi. dan ternyata aspirin ini menghambat enzym cox di bagian (residu) serin-530 .

 

aspirin ini sangat unik, karena Beliau (karena obat ini tua banget usianya, udah 100 tahun lebih dipakai) bereaksi secara kovalen dan sifat dari reaksinya adalah ireeversible.

image  Nah…jika ada pertanyaan bagaimana mekanisme reaksinya?

akan andy jawab..

Pada mekanisme reaksi suatu reaksi kimia dalam enzym, kondisi berjalan lunak karena ada bantuan dari enzym- enzym tersebut.

 

Ternyata pada asetalisasi cox oleh aspirin, Senyawa carbonil dari aspirin di ganggu kestabilannya oleh residu Tyr 385 secara langsung dan residu Tyr 348 secara tidak langsung.

tahap 1 :

image Tahap 2 (C karbonil aspirin kekurangan elektron)

image Tahap 3 (gugus Hidroksil serin 530) berperan sebagai nucleofil menyerang C karbonil yang bersifat elektrofil (kekurangan elektron) :

image

Tahap 4 (gugus hidroksil serin menjadi kekurangan elektron sehingga terjadi protonasi/pelepasan proton)image Tahap 5 (gugus carbonil kembali beresonansi). Namun, karena sekarang gugus ester (O-fenil) merupakan leaving group yang baik, maka akan terlepas.

image tahap 6 Serin 530 teracetilkan sehingga in aktif dalam mengubah arachidonat acid menjadi PGG (anti inflamatory drug berhasil) image

Tahap 7. Hasil akhir menjadi senyawa di bawah ini :

 

image Oke…sekian lah..

oh iya…sebenernya dengan kit tahu struktur senyawa tersebut, karena banyak gugus OH nya, senyawa ini akan langsung dimetabolisme pad fase 1 atau G tau ding…

bereaksi dengan glukoronat dkk…

 

 

oke titis, ini jawaban dariku..sekian dan sukses buat seminarnya….

^^

DAFTAR PUSTAKA

G. Phillip Hochgesang, Jr., Scott W. Rowlinson, and Lawrence J. Marnett ,Tyrosine-385 Is Critical for Acetylation of Cyclooxygenase-2 by Aspirin, J. Am. Chem. Soc. 2000, 122, 6514-6515

776 Comments on Mekanisme aspirin menghambat Cycloooxygenase (Pertanyaan dari Titis FSI 06)

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