Cell-penetrating Peptide Synthesis

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Cell-penetrating Peptide Synthesis

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Peptide synthesis: Cell Penetrating Peptide Oligonucleotide Conjugate

Amino acid sequences and properties of CPPs

Tat, the transcription activator of the human immunodeficiency virus type 1 (HIV-1) viral genome, enters cells in a non-toxic and highly efficient manner. Tat is the first known cell-penetrating peptide.

CPPs have been used as a carrier to deliver proteins or genes into cells and tissues. In this study, a CPP library composed of 55 CPPs were used to deliver genes into plant cells. Many CPPs showed efficient penetration into plant cells. The Lys-containing CPPs have higher penetration efficiency in the plant than in animal cells. This could be due to differences in lipid composition and surface charge of the cell membranes. No correlations were detected between the penetration efficiency and the cationic, amphipathic, or hydrophobic properties of peptides.

D-R9 is composed of D-form amino acids. D-R9 bound preferentially to the membrane and did not penetrate the cytosol or vacuole. In mammalian cells, poly-Lysine-based CPPs are efficient and interact with membrane lipid head groups to induce wrapping of the membrane monolayers. Arg-rich peptides, such as the Tat peptide, are among the most efficient CPPs. Arg-rich CPPs may generate negative Gaussian membrane curvature to form pores or protrusions from endocytosis. The cell penetration efficiency of CPPs containing poly-Arg is higher than those containing poly-Lys. However, in the plant, Arg-rich CPPs are not the most efficient at penetrating plant cell.

Peptide No. CPP Amino acid sequence Number of amino acids CPP type:
C: cationic, A: amphipathic, H: hydrophobic.
Net charge at pH7
1 BP100 KKLFKKILKYL 11 A 5
2 2BP100 KKLFKKILKYLKKLFKKILKYL 22 C 10
3 Rev(34–50) TRQARRNRRRRWRERQR 17 C 9
4 R9 RRRRRRRRR 9 C 9
5 D-R9 rrrrrrrrr (D form) 9 C 9
6 R12 RRRRRRRRRRRR 12 C 12
7 KH9 KHKHKHKHKHKHKHKHKH 18 C 9.9
8 K9 KKKKKKKKK 9 C 9
9 K18 KKKKKKKKKKKKKKKKKK 18 C 18
10 Pen2W2F RQIKIFFQNRRMKFKK 16 C 7
11 DPV3 RKKRRRESRKKRRRES 16 C 10
12 6-Oct GRKRKKRT 8 C 6
13 R9-TAT GRRRRRRRRRPPQ 13 C 9
14 Tat(49–57) RKKRRQRRR 9 C 8
15 Retro - Tat(57–49) RRRQRRKKR 9 C 8
16 Sc18 GLRKRLRKFRNKIKEK 16 A 8
17 KLA10 KALKKLLAKWLAAAKALL 18 A 5
18 IX QLALQLALQALQAALQLA 18 H 0
19 XI LKTLATALTKLAKTLTTL 18 H 3
20 No. 14–12 RAWMRWYSPTTRRYG 15 A 4
21 pVEC LLIILRRRIRKQAHAHSK 18 A 6.2
22 PenArg RQIRIWFQNRRMRWRR 16 A 7
23 M918 MVTVLFRRLRIRRACGPPRVRV 22 A 6.9
24 Penetratin RQIKIWFQNRRMKWKK 16 A 7
25 PolyP 3 (SAP) VRLPPPVRLPPPVRLPPP 18 H 3
26 dhvar5 LLLFLLKKRKKRKY 14 A 7
27 HPV33L2-445/467 SYFILRRRRKRFPYFFTDVRVAA 23 A 6
28 buforin II (5–21) RAGLQFPVGRVHRLLRK 17 A 5.1
29 scrambled pVEC IAARIKLRSRQHIKLRHL 18 A 6.2
30 HPV33L2-DD447 SYDDLRRRRKRFPYFFTDVRVAA 23 A 4
31 LAH4 KKALLALALHHLAHLALHLALALKKA 26 H 4.4
32 ppTG1 GLFKALLKLLKSLWKLLLKA 20 A 5
33 Transportan (TP) GWTLNSAGYLLGKINLKALAALAKKIL 27 H 4
34 2 × ppTG1 GLFKA LLKLL KSLWK LLLKA GLFKA LLKLL KSLWKLLLKA 40 A 10
35 pAntpHD(Pro50) RQIKIWFPNRRMKWKK 16 A 7
36 pAntp(44–58) QIKIWFQNRRMKWKK 15 A 6
37 Crot(27–39) KMDCRWRWKCCKK 13 A 4.8
38 Crot(27–39) derevative (1) MDCRWRWKCCKK 12 A 3.8
39 Crot(27–39) derevative (2) KCGCRWRWKCGCKK 14 A 5.7
40 CyLoP-1 CRWRWKCCKK 10 A 4.8
41 Inv3 TKRRITPKDV IDVRSVTTEINT 22 H 2
42 Inv5 AEKVDPVKLN LTLSAAAEALTGLGDK 26 H -1
43 Inv3.5 TKRRITPKDV IDVRSVTTKINT 22 H 4
44 Inv3.10 HHHHHH TKRRITPK DVIDVRSVTTEINT 28 H 2.6
45 ARF(1–22) MVRRFLVTLRIRRACGPPRVRV 22 A 6.9
46 Cyt C 77–101 GTKMIFVGI KKKEERADLIAYLKKA 25 A 4
47 hLF peptide KCFQWQRNM RKVRGPPVSCIKR 22 A 6.9
48 Glu-Oct-6 EEEAAGRKRKKRT 13 A 3
49 M511 FLGKKFKKYFLQLLK 15 A 5
50 G53-4 FLIFIRVICIVIAKLKANLMCKT 23 H 3.9
51 M591 YIVLRRRRKRVNTKRS 16 A 8
52 E162 KTVLLRKLLKLLVRKI 16 A 6
53 E165 LLKKRKVVRLIKFLLK 16 A 7
54 M867 KKICTRKPRFMSAWAQ 16 A 4.9
55 MG2d GIGKFLHSAKK WGKAFVGQIMNC 23 H 4
56 Antitrypsin (358-374) CSIPPEVKFNKPFVYLI 17 H 0.9
57 BAC715-24 PRPLPFPRPG 10 A 2
58 BMV Gag-(7-25) KMTRAQRRAAARRNRWTAR 19 C 8
59 BUFORIN II TRSSRAGLQFPVGRVHRLLRK 21 A 6.1
60 CADY Ac-GLWRALWRLLRSLWRLLWRA-cysteamide 21 H 4
61 CCMV Gag-(7-25) KLRTRAQRRAAARKNKRNTR 20 C 10
62 ARF Peptide (26-44) H-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg -D-Arg-D-Arg-D-Arg-D-Arg-Lys -Phe-Val-Arg-Arg-Ser -Arg-Arg-Pro-Arg-Thr- Ala-Ser-Cys-Ala-Leu- Ala-Phe-Val-Asn-OH 29 A 14.9
63 FHV COAT-(35-49) RRRRNRTRRNRRRVR 15 C 11
64 Calcitonin LGTYTQDFNKFHTFPQTAIGVGAP 24 H 0.1
65 HN-1 TSPLNIHNGQKL 12 H 1.1
66 HTLV-II Rex-(4-16) TRRQRTRRARRNR 13 C 8
67 Human P: MGLGLHLLVLAAALQGAWSQPKKKRKV 27 H 5.1
68 Human P MGLGLHLLVLAAALQGAWSQPKKKRKV 27 H 5.1
69 K-FGF AAVALLPAVLLALLAP 16 H 0
70 Ku70 VPMLKPMLKE 10 A 1
71 MAP KLALKLALHA LKAALKLAKL ALKLALKALK AALKLA-NH2 36 H 10.1
72 Maurocalcine GDC(acm)LPHLKLC 10 H 0
73 Neurturin GAAEAAARVYDLGLRRLRQRRRLRRERVRA 30 A 8

Other examples are:

  • Antennapedia (43-58):RQIKIWFQNRRMKWKK;
  • Antitrypsin (358-374): CSIPPEVKFNKPFVYLI;
  • BAC715-24: PRPLPFPRPG;
  • BMV Gag-(7-25): KMTRAQRR AAARRNRWTAR;
  • BUFORIN II: TRSSRAGLQF PVGRVHRLLRK;
  • CADY: Ac-GLWRALWRLLR SLWRLLWRA-cysteamide;
  • CCMV Gag-(7-25): KLRTRAQRRAAARKNKRNTR;
  • ARF Peptide (26-44): H-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg-D-Arg -D-Arg-D-Arg-D-Arg-Lys-Phe-Val-Arg-Arg-Ser-Arg -Arg-Pro-Arg-Thr-Ala-Ser-Cys-Ala-Leu-Ala-Phe-Val-Asn-OH
  • D-TAT: Grkkrrqrrrppq-NH2;
  • FHV COAT-(35-49): RRRRNRT RRNRRRVR;
  • hCT (9-32) Calcitonin: LGTYTQDFNKF HTFPQTAIGVGAP;
  • HIV-1 Rev (34-50): TRQARRNRR RRWRERQR;
  • HN-1: TSPLNIHNGQKL;
  • HTLV-II Rex-(4-16): TRRQRTRRARRNR;
  • Human P1: MGLGLHLLVLAA ALQGAWSQPKKKRKV;
  • K-FGF: AAVALLPAVLLALLAP;
  • Ku70: VPMLKPMLKE;
  • MAP: KLALKLALHALKAALKLAKL ALKLALKALKAALKLA-NH2;
  • Maurocalcine: GDC(acm)LPHLKLC;
  • MPG: Ac-GALFLAFLAAALSLMGLWSQPKKKRRV-Cya;
  • MPG(ΔNLS): Ac-GALFLGFLGAAGS TMGAWSQPKKKRKV-Cys;
  • Neurturin: GAAEAAARVYDLGL RRLRQRRRLRRERVRA;
  • P22 N-(14-30): NAKTRRHERRRKLAIER;
  • Pen2W2F: Fluo-RQIKIFFQNRRMKFKK-NH2;
  • Penetratin-Arg: RQIRIWFQNRRMRWRR;
  • Penetratin: RQIKIWFQNRRMKWKKGG;
  • Pep-1: Ac-KETWWETWWTEWSQPKKKRKV-Cys;
  • Pep-2: Ac-KETWFETWFTEWSQPKKKRKV-Cys;
  • Pep-7: SDLWEMMMVSLACQY;
  • plsl-1: RVIRVWFQNKRCKDKK;
  • pVEC (Cadherin-5): LLIILRRRIRKQAHAHSK;
  • R7W: Fluo-RRRRRRRW-NH2;
  • RVG-9R: YTIWMPENPRPGTP CDIFTNSRGKRASN GGGGRRRRRRRRR;
  • SAP: VRLPPPVRLPPPVRLPPP;
  • SV-40 Large T-antigen Nuclear Localization Signal:CGGGPKKKRKVED;
  • SynB1: RGGRLSYSRRRFSTSTGR;
  • SynB3: RRLSYSRRRF;
  • HIV-1 Tat (48-60):GRKKRRQRRRPPQ;
  • TAT (HIV-1 (48-61)): GRKKRRQRRRPPQQ;
  • TAT (HIV-1 (49-57)): RKKRRQRRR;
  • TAT (47-57): YGRKKRRQRRR;
  • TAT R9: GRRRRRRRRRPPQ;
  • TAT P59W: Fluo-GRKKRRQRRRPWQ-NH2;
  • TAT-HA2 Fusion Peptide: RRRQRRKKRGGD IMGEWGNEIFGAIAGFLG;
  • Temporin L: FVQWFSKFLGRIL-NH2;
  • Transportan: GWTLNSAGYLLGKINLKALAALAKKIL;
  • VP-22: DAATATRGRSAASRPTE RPRAPARSASRPRRPVD;
  • PTD-4: PIRRRKKLRRLK;
  • PTD-5: RRQRRTSKLMKR;
  • SBP: MGLGLHLLVLAAALQGAWSQPKKKRKV;
  • FBP: GALFLGWLGAAGSTMGAWSQPKKKRKV;

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