M elittin,. G IGAVL KVL T T GL PAL ISW IKR KRQQ N H 2. M elittin 5, 4 C (KR KR ). M elittin, 1. 1
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1 V ol. 24 N o CHEM ICAL JOU RNAL O F CH IN ESE UN IV ERS IT IES , 1, 1, 1, 2 (1.,, ; 2. ALBA CH EM L im ited & the Edinburgh Centre for P rotein Technology, D epartm ent of Chem istry, the U niversity of Edinburgh, K ing s Building, W est M ains Road, Edinburgh, Scotland, EH 9 3JJ, U K) ittin (G IGAVL KVL TTGL PAL ISW IKR KRQQ N H 2) 26,,. C 15 ( GL PAL ISW IKR KRQQ N H 2) (15 ). ittin.,,,. (KR KR ).. (Α2 ). ittin; ; ; Q 516 A (2003) , 6.,. [1, 2 ],, (CeC rop ia moth) (Cecrop in) ; (M againin) (D efensin).,,.,, [3 ].,...,,,. (ittin) (A p ism ellifera), 26, G IGAVL KVL T T GL PAL ISW IKR KRQQ N H 2. ittin 5, 4 C (KR KR ). ittin, [4 ]. ittin,. ittin C 15,, (Boc) L A dvanced Chem T ech, A rg, L ys, Ser O 2, T rp. 12 (HOB t) (DM A P) A CRO S, 1, 22 (ED T ) M erck. (S. auveus) (B. subtilis), : : ( : ). : (1959 ),,,,,.
2 450 V ol. 24, 4.. W aters, (ΛBONDA PA KTM C nm, 10 Λm, 19 mm 300 mm ) ; (N ova2pak C 18, 4 Λm, 3. 9 mm 150 mm ). H F, L 8500, UV , JA SCO 2J2715, AB I A P I ittin [ 5 ], ittin ittin M BHA (0. 71 mmol N g), Boc (DCCgHOB t),,. Boc2L eu Boc2Ile,, DM A P HOB ṫ, 5% ED T H F 0 60 m in,. Sephadex G215, % g ( 0. 1% T FA ), (H am ilton ) 10 ΛL, ( 20 ), 28% g (0. 1% T FA ), 0. 9 ml gm in, 214 nm ΛggmL., h, ,, 1 ml 1 ml,, h, (M IC) PBS, ( 2. 5% ). PBS,, 0. 5 ml 2. 5%, PBS 1. 0 ml,, m in, rgm in 10 m in, 414 nm, PBS, T riton X % cm T ris2hc l(ph = 7. 5) 30 mmolgl SD S (CD ), nm, 4, 50 nm gm in, ΛmolgL. [Η], f h= ( [Η]222- [Η] 0 222) g[η] , [Η] nm ; [Η] [Η] % 222 nm, [6 ] ittin, [7 ],. [8 10 ], ittin [(12 26) ], ittin, [11 ]., 6 Α2 [8, 9 ], (12 26) AL ISW İ 6 2, 6 Α2, C, M BHA, H F C. ittin.
3 N o. 3 : 451 ( 2). (12 26) (12 26, L 7 ) ES , ( ),. Table 1 Sequences of peptides Sequence Sequence (12 26) GL PAL ISW IKRKRQQ NH 2 (12 26, L 4 ) GL PLL ISW IKRKRQQ NH 2 (12 26, L 3 ) GLLAL ISW IKRKRQQ NH 2 (12 26, L 7 ) GL PAL ILW IKRKRQQ NH 2 3 Am ino Table 2 Am ino Ac id Ana lysis of peptides 3 Am ino acid (12 26) (12 26, L 3 ) (12 26, L 4 ) (12 26, L 7 ) acid (12 26) (12 26, L 3 ) (12 26, L 4 ) (12 26, L 7 ) Ser (1) (1) (1) (0) L eu (2) (3) (3) (3) Glu (2) (2) (2) (2) L ys (2) (2) (2) (2) Gly (1) (1) (1) (1) A rg (2) (2) (2) (2) A la (1) (1) (0) (1) P ro (1) (0) (1) (1) Ile (2) (2) (2) (2) Theoretical ratio in parentheseṡ 2. 2 Kyte [12 ] 2 K 2D, 6 K 2D 429 K 2D 1215, 3. K 2D,. Table 3 Hydrophobic ities of peptides K 2D 4 9 K 2D 1 15 trgm in K 2D 4 9 K 2D 1 15 trgm in (12 26) (12 26, L 4 ) (12 26, L 3 ) > 80 (12 26, L 7 ) R P2H PL C C18 (tr).,. 3, K 2D 1 15 tr. (12 26, L 3 ) K 2D 1 15 tr,, tr (12 26, L 3 ) K 2D 1 15,, Α2 [13 ],,. Chou2Fasm an [14 ], 3 (12 26, L 3 ) Α2. CD ittin (S. auveus) (B. subtilis) (M IC ). ittin 1. 0 ΛggmL. (12 26), (12 26), (12 26), tr. (12 26) 6, (12 26, L 4 ) (12 26, L 7 ),. ittin,. Chou2Fasm an [14 ], (12 26, L 4 ) Α2 (12 26, L 7 ), CD,,. [ 8, 9 ], 6. (12 26) 6, (12 26, L 3 ), ittin,
4 452 V ol. 24,. Table 4 An tibacter ia l activ ities of ittin and its ana logous M ICg(Λg ml - 1 ) S. auveus B. subtilis M ICg(Λg ml - 1 ) S. auveus B. subtilis ittin (12 26, L 4 ) (12 26) (12 26, L 7 ) (12 26, L 3 ) ittin 10 ΛggmL, 100% ; 50% (HC50) 5 ΛggmL. (12 26) (1 800 ΛggmL ). 5 m ggml, 10%. (12 26, L 3 ), (12 26, L 4 ) (12 26, L 7 ) HC50 120, ΛggmL, ittin (12 26) M IC,. ittin 4, K 2D B londelle [4 ],,.,, (12 26) ittin, ;, (12 26, L 4 ) (12 26, L 7 ), (12 26, L 7 ), (12 26, L 7 ).,. F ig. 1 Hemolysis of human erythrocytes a s a function of peptide concen tra tion s ittin; ( ) ; ( 12 26, L 3 ) ; (12 26, L 4 ) ; (12 26, L 7 ) F ig. 2 C ircular dichro ism (CD ) spectra of peptides ittin; ( ) ; ( 12 26, L 3 ) ; (12 26, L 4 ) ; (12 26, L 7 ), in aqueous buffer (open sym bols) and 30 mmolgl SDS (closeded sym bols). ( 2), ittin,. SD S, nm, Α2. SD S,. SD S Α2. T ris2hcl Table 5 Ca lcula ted percen tages of Α-hel ix in peptides SDS - [Η]222 f h - [Η]222 f h T ris2hcl SDS - [ Η]222 f h - [Η]222 f h ittin (12 26, L 4 ) (12 26) (12 26, L 7 ) (12 26, L 3 ) Α2. Α2, Α2, (12 26) (12 26,
5 N o. 3 : 453 L 3 ), Α2 (12 26). (12 26, L 4 ) Α2 (12 26, L 7 ),. 5 4, Α2, Ziv [15 ] Α2. [ 1 ] Zasloff M.. P roc. A cad. Sci. U SA [J ], 1987, 84 (8) : [ 2 ] Deborah A. S., M alinda A. H., Craig A. T. et al.. A ntim icrob. A gents Chemotherapy[J ], 1997, 41 (8) : [ 3 ] Ziv O., J iang H., Yechiel S.. J. B iol. Chem. [J ], 1997, 272 (23) : [ 4 ] B londelle S. E.. Houghten R. A.. B iochem. [J ], 1991, 30 (19) : [ 5 ] Vogel H., Jahnig F.. B iophyṡ J. [J ], 1986, 50 (8) : [ 6 ] Tosteson M. T., Holm es S. T., Razin M. et al.. J. M em bṙ B iol. [J ], 1985, 87 (1) : [ 7 ] FAN G Zhu ( ), YAN G Yu2L in ( ), ZHOU Bang2Xun ( ). Studies and App lications on Toxins( ) [M ], Beijing: Science P ress, 1988: [ 8 ] YAN Hu2Sheng, HE B ing2l in. Chinese J. B iochem. B iophyṡ [J ], 1992, 24 (4) : [ 9 ] Yan H. S., N i A. G., L iu L. P. et al.. Science in China, Series B [J ], 1996, 39 (2) : [ 10 ] L iu L. P., Yan H. S., N i A. G. et al.. Inṫ J. P rotein Reṡ [J ], 1994, 43 (1) : [ 11 ] L iu L. P., Xie Z. D., Yan H. S. et al.. s: B iology and Chem istry[m ], N etherlands: L eiden, ESCOM, 1995: [ 12 ] Kyte J., Doolittle R. F.. J. M ol. B iol. [J ], 1982, 157 (2) : [ 13 ] B ttner K., B londelle S. E., O stresh J. M.. B iopolym ers[j ], 1992, 32 (6) : [ 14 ] Chou P. Y., Fasm an G. D.. A dv. Enzymol. [J ], 1978, 47 (1) : [ 15 ] Ziv O., Yechiel S.. J. B iol. Chem. [J ], 1996, 271 (13) : Studies on Syn thesis and Biological Activities of Analogues of ittin L I Shun2Zi 1, YAN H u2sheng 13, L IU Guo2Dong 1, H E B ing2l in 1, J IAN G L u 2 (1. S tate K ey L aboratory of F unction P olym er M aterials f or A d sorp tion and S ep aration, Institute of P olym er Chem istry, N ankai U niversity, T ianj in , Ch ina; 2. A L B A CH EM L im ited & the E d inburg h Centre f or P rotein T echnolog y, D ep artm ent of Chem istry, the U niversity of E d inburg h, K ing s B uild ing, W est M ains R oad, E d inburg h, S cotland, EH 9 3J J, U K ) Abstract ittin (G IGAVL KVL T T GL PAL ISW IKR KRQQ N H 2), a 262residue pep tide, is the m ajor component of the venom of the honey bee A p ism ellifera, exh ibits h igh ly potent antibacterial activity in ad2 dition to its hemolytic activity. A pep tide corresponding to ittin s C2term inal 15 residues and 4 ana2 logues w ith 15 residues, respectively, w ere designed and syn thesized. T he pure pep tides w ere obtained by sem i2p reparative R P2H PL C. A nalytical R P2H PL C show ed a single peak and am ino acid analysis show ed that the pep tides had expected am ino acid com po sition ṡ A n tibio tic activities, hem o lytic activities, hy2 drophobicities and secondary structures of the pep tides w ere studied. A ll these analogues exh ibited po ten t antibacterial activities and had m uch decreased abilities to lyse hum an red blood cellṡ ties w ere rough ly co rrelated w ith the hydrophobicitieṡ T he antibiotic activi2 T he hydrophobicities of the residues farther from the basic cluster (KR KR ), how ever, contributed more to the antibiotic activitieṡ W h ile the m echanism of hemolysis of pep tides is not the sam e as antibacterial action. N o clear correlation betw een the hydrophobici2 ties o r the hem o lytic activities and the secondary structures(α2helical structures) w as found. Keywords ittin; A ntibacterial activity; H emolytic activity; CD spectrum (Ed. : H, J, Z)
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